Roots & Rhinestones

When I was a sophomore in high school, I applied to be a volunteer at The Vinny, a charity golf tournament hosted by Vince Gill to benefit the Tennessee Junior Golf Association. 

I was just learning the sport and wasn’t familiar with many professional golfers. But I loved country music and had seen photos in Country Music Magazine of some of my favorite stars playing in The Vinny. One memorable shot was of Reba, shoulders hunched up to her ears with a worried expression on her face, after hitting a wayward shot that nearly hit a spectator. 

I was thrilled to receive a letter saying I had been selected. 

After a full day of pro-am action in the hot June sun, Vince gave an exclusive concert at the Grand Ole Opry. The junior volunteers sat in the back of the floor section and listened as Vince told jokes and stories, apologized for any cuss words uttered during his round, and invited his musical buddies to join him on stage. 

The next day, we were back on the course for the celebrity-amateur portion of the tournament. Reba wasn’t there, but plenty of great singers made the day fun for me and my parents. 

I went back in 1998, but the tone had shifted dramatically. Vince still told jokes, swore on the course, and signed autographs, but he was clearly hurting. When they unveiled a statue his late father Stan at Golf House, where the junior volunteers stayed, Vince sobbed openly. And at the Opry, he broke down during “I Still Believe in You,” imploring the crowd to sing the lyrics he couldn’t finish. 

The death of his dad and the dissolution of his first marriage in 1997 made for a tough year for the affable Vince, but his actions were a lesson in graciousness. Even in his grief, Vince made time for his fans. 

After the media and special guests left the statue unveiling, Vince spent a few moments admiring the memorial, which depicts a 10-year-old Vince completing his golf swing. His dad is resting a hand on Vince’s shoulder. 

A junior volunteer handed me his camera and asked Vince for a photo. Vince put his arm around the young man’s shoulders and smiled. I snapped the photo and shyly handed it back to the kid without asking for my own picture with Vince. 

That wasn’t like me back then. I was much bolder two days later when I stopped Kix Brooks in the parking lot for a photo. But Vince’s vulnerability left me a little shaken.  

In that summer of ‘98, Vince Gill showed a glimpse of the caretaker he would become — revered for his generosity as much as his talent. 

Triple Threat 

You know one of the things I miss most about the music I grew up on? The packaging. 

Cassette tapes and CDs came with glossy liner notes that included artist photos, song lyrics, credits, and thank-you notes that I read religiously. It’s how I learned Vince Gill was a triple threat: singer, songwriter, and musician. 

As my collection of country music grew, I loved finding his name in the liner notes of other artists’ work like Reba’s “You Lie” and Dolly’s “Silver and Gold.”  

Vince was a bankable bet on the charts when I started digging into his music, but he had already been on the road for nearly two decades. From regional bluegrass bands to Pure Prairie League to Emmylou Harris’s Hot Band, Vince spent those first years making friends and admirers. 

In 1984, he won the ACM Top New Male Vocalist award, but it would take another six years for him to break through in country music. “When I Call Your Name” earned him his first of 18 CMA Awards and his first of 22 Grammys. 

While that sounds like a recipe for chart success, I was surprised to learn Vince has just four U.S. No. 1’s as a solo artist. That’s four more than I’ll ever have, but his success — and legacy — reach beyond the charts. 

“Go Rest High on That Mountain” peaked at No. 14 but has only grown in popularity in the 30 years since its release. Vince and Patty Loveless, who sang background vocals with Ricky Skaggs on the single, delivered a now-legendary performance of the song at George Jones’s 2013 memorial service. 

Just like that night in 1998 at the Opry, Vince wore his heart on his sleeve and wept openly. And just like that ‘98 crowd, Patty sang the lines he couldn’t finish. 

Don’t misread it. Men who cry aren’t fragile. Vince certainly isn’t fragile — he’s a man of deep feeling. He sings with his eyes shut tight to stay inside the song, and he plays guitar as if it’s an extension of his body. 

Country music has plenty of guitar heroes, but Vince plays differently. His electric solos aren’t about showing off. They’re expressions of the song’s emotional center. 

It’s true in tender ballads like “You and You Alone” and in honky-tonkers like “What the Cowgirls Do.” Vince sings with his guitar as much as his voice. 

As his own star rose, Vince continued to lend his voice and guitar to a host of artists across all genres. And as country music lost the voices that inspired Vince, he stepped in to fill their shoes as a mentor and friend to dozens of newcomers. 

The Statesman 

I’ve been lucky to see Vince Gill live several times over the years, and I never tire of his artistry. But one of my clearest memories of Vince on stage has nothing to do with performing. 

In 2017, my parents and I went to the Opry for the 40^th anniversary of Reba’s debut there. Vince hosted her segment and caught my eye during a commercial break. With techs bustling to move mics as musicians took their places, Vince — guitar slung comfortably at his side — wandered from the side of the stage to the emcee’s lectern. 

He leaned against the podium, peering over the emcee’s shoulder, completely at home. And during the COVID-19 pandemic, Vince was integral in keeping the Opry the longest-running live radio broadcast in U.S. history. When live audiences were barred, Vince performed acoustic sets with Brad Paisley and Marty Stuart, his wife Amy Grant and daughters Jenny and Corinna, and Reba. 

And Vince was on the first show welcoming the live audience back in October 2020, showing he’s more than an Opry member. He’s a patriarch, taking the mantle from Roy Acuff, Porter Wagoner, and Little Jimmy Dickens. 

He supports new artists regardless of how their sound varies from his own. In a 2015 interview with Dan Rather during the bro country era, the legendary broadcaster teed up Vince for a monster drive.  

Vince, a student of Merle Haggard and Ralph Stanley, and with the credentials and every right to call out the checklist songwriting of the day, laid up instead.  

He admitted some of the day’s music wasn’t his “cup of tea” but showed signature graciousness and respect for artistic expression, saying “There’s a lot of it I’m not crazy about it, but it’s not personal. They don’t have anybody cheering for them harder than I do.” 

I’ve also been lucky to see Vince’s generosity in person, not only at The Vinny but at my alma mater, Belmont University, where he hosted charity basketball games to benefit our athletic and music business programs. 

Vince isn’t an alumnus, but he enjoys a close friendship with retired men’s basketball coach, Rick Byrd, who plays golf with Vince in his “One More Last Chance” music video. Students and fans were used to seeing Vince at games — and hearing him heckle the referees. 

And when his oldest daughter moved into the dorm, Vince was like any other dad, dutifully hauling her mini fridge up the stairs and to her room. That regular-guy charm is endearing and approachable. 

But fans know that Vince is an extraordinary talent. Here are five songs that showcase Vince’s unmistakable voice, songwriting prowess, and guitar greatness, along with three of my favorite album cuts. 

My Top 5 Vince Gill Songs 

1. “High Lonesome Sound” 

From his 1996 album of the same name. Written by Vince Gill. Peaked at No. 12 on the Billboard Hot Country Songs chart. 

Vince recruited Alison Krauss to sing harmony on his ode to bluegrass. It’s a magical combination, with Alison singing just above Vince’s warm tenor to create something spiritual. While the instrumentation includes traditional bluegrass, Vince took it a step further by closing the album with an alternate version of the song featuring Alison and Union Station. 

2. “Don’t Let Our Love Start Slippin’ Away” 

From his 1992 album I Still Believe in You. Written by Vince Gill and Pete Wasner. No. 1 on the Billboard Hot Country Songs chart. 

I can’t argue that Vince is at his best when he’s writing and singing about heartbreak, but my favorite Vince shows up on songs like this one. His bright vocals shine on this up-tempo track, and his guitar solo adds depth that makes the single more than just a bop. Paired with a music video that saw some of his industry buddies having a ball in a club, it’s easy to see why Vince is known as one of the nicest guys in Nashville. 

3. “Trying to Get Over You” 

From his 1992 album I Still Believe in You. Written by Vince Gill. No. 1 on the Billboard Hot Country Songs chart. 

This is Vince at his best — writing an achingly beautiful song about the kind of heartbreak that takes dying to get over. The warmth of his voice creates an intimacy that invites us into his despair. And the guitar solo doesn’t feel ornamental but as grief-stricken as the song’s narrator. 

4. “When I Call Your Name” 

From his 1990 album of the same name. Written by Vince Gill and Tim DuBois. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

Vince had been recording music as a solo artist since the mid-80s and playing live for even longer when this song catapulted him to stardom. “When I Call Your Name” should be required text for any country songwriter, but the song would lose some of its emotional weight without Patty Loveless’s Appalachian lonesomeness on harmony. 

5. “When Love Finds You” 

From his 1994 album of the same name. Written by Vince Gill and Michael Omartian. Peaked at No. 3 on the Billboard Hot Country Songs chart. 

When Love Finds You is one of Vince’s best albums, featuring six singles, at least two of which remain staples among modern country music fans. “Whenever You Come Around” and “Go Rest High on That Mountain” may eclipse the title track in popularity or staying power, but Vince turns “When Love Finds You” into a soulful, hopeful prayer even a cynic can believe. 

Bonus Album Cuts 

“I Can’t Tell You Why” 

From the 1993 album Common Thread: The Songs of the Eagles. Written by Timothy B. Schmit, Don Henley, and Glenn Frey. 

Long before the Eagles tapped Vince to replace the late Glenn Frey in 2017, he returned to his soft-rock roots on this tribute album. But his silky vocals also allow him to play in the R&B sandbox where he’s at home on his 1998 hit “If You Ever Have Forever in Mind.” 

“No Future in the Past” 

From his 1992 album I Still Believe in You. Written by Vince Gill and Carl Jackson. 

The piano intro recalls the great country standards of Patsy Cline and Ray Price, and Vince’s delivery matches that vintage sound.  

“What They All Call Love” 

From his 1998 album The Key. Written by Vince Gill. 

Vince supplied the background vocals on Faith Hill’s No. 1 hit “Let Me Let Go,” and she returned the favor here. We don’t talk about their voices together enough, but their pairing is as rich as his work with Reba. It’s a shame we didn’t get more Vince and Faith through the years. 

Thanks for taking this walk down memory lane with me. Vince Gill is a gift to country music — a devoted caretaker of its history and stalwart defender of its evolution. Let me know your favorite Vince song or story in the comments. 

Fans of The Office will remember Andy Bernard’s prescient quote from the series finale: “I wish there was a way to know you’re in the good old days before you’ve actually left them.” 

Though sincere in his gratitude for his time at Dunder Mifflin, Andy’s feelings are colored by the emotion of the evening. Nostalgia has that effect on us. 

The ‘90s were a golden era in country music, but the decade was far from perfect. Sexism was still rampant, with some radio stations refusing to play more than one female artist per hour.  And in the rush to capitalize on the genre’s global popularity, record labels didn’t always get it right. 

Fans didn’t always get it right either. At least, I didn’t. 

There were some artists I seriously disliked back then who became favorites, and others I loved who just don’t hit me the same anymore. It’s not a reflection on them so much as a testament to how my preferences have changed over the years. 

Yours probably have too. Our listening “palate” develops, and our relationship with the music from our formative years evolves. 

Here are five artists I first heard in the ‘90s that I now hear differently. 

Alison Krauss 

In 1995, Alison Krauss had a monster night at the CMA Awards, taking home four trophies: Horizon Award, Female Vocalist of the Year, Vocal Event of the Year with Shenandoah, and Single of the Year for “When You Say Nothing at All.” 

The song was everywhere, but I was 14 and unimpressed. It’s embarrassing to admit that I didn’t like Alison’s pure, crystalline voice. In hindsight, I can make some sense of that. I was listening to powerhouse vocalists like Reba, Martina McBride, and Faith Hill — singers who belted, soared, and filled every corner of a song. 

I had never heard a voice like Alison’s and didn’t know what to do with the softness. 

In college, I gave Alison another listen when I heard my friends rave about her. Thank God for positive peer pressure! I wore out her Live CD and even asked Santa for the DVD. Suddenly, I couldn’t understand how anyone could overlook Alison Krauss. As an adult, it became a running joke with a good friend who reacted to Alison’s voice with instant dislike as I once did. 

Since then, I’ve been fortunate to see Alison Krauss and Union Station in concert twice — once at the Ryman in Nashville and more recently at the Orpheum in Memphis. Both were special experiences that had me closing my eyes to fully immerse myself in the music, but the Arcadia tour stop at the Orpheum leveled up the intimacy. 

For their encore, Alison and the band gathered around a single microphone and sang a handful of songs, recalling the early days of bluegrass before every instrument or singer was plugged into a monitor. It’s a memory I hope I’ll never forget. 

You’ll have to wait for my blog about Alison Krauss for my Top 5 songs. For now, I’ll give you one example of how Alison can take a song from any genre and make it unmistakably hers. 

“Baby Mine” 

From the 1996 compilation album The Best of Country Sing the Best of Disney and her 2007 A Hundred Miles or More: A Collection album. Written by Frank Churchill and Ned Washington. 

The song first appeared in Dumbo as a lullaby sung by Dumbo’s mother and was nominated for Best Original Song at the 1942 Academy Awards. It’s a piece of film history, but Alison elevates it from sentimental to pristine. You don’t catch yourself thinking, “Hey, wasn’t this song in Dumbo?” Her version is fresh and elegant without losing the tenderness of the original. She adds strings for a lusher arrangement that still pairs perfectly with her bluegrass roots, creating something unexpected that fits her perfectly. 

Tanya Tucker 

When “Two Sparrows in a Hurricane” put Tanya Tucker back in the awards-show conversation in 1992, I had no idea she was already a bona fide star. And I did not like that song. 

I was only in sixth grade, but I had plenty of opinions about music. To my untested ears, Tanya’s husky voice didn’t fit the picture painted in the song’s lyrics — two teenagers falling in love, getting married, having a family and fighting the headwinds of life together. It’s a lovely story that starts with the line “She’s fifteen and he’s barely driving a car,” which songwriter Mark Alan Springer masterfully adapts in the last verse to “She’s eighty-three and he’s barely driving a car.” 

If anyone else had sung it, I’d probably be giving it a chef’s kiss. 

“Two Sparrows” didn’t land for me, but Tanya Tucker was recording a lot of music I really did like: “If Your Heart Ain’t Busy Tonight” and “Hangin’ In” were perfect vehicles for her signature sass. And “Soon,” a song about a married man promising his lover they’ll be together soon, is well suited for her throaty delivery. 

Still, it would be decades before I went back through Tanya’s catalog to learn what made her a star in the first place. Hearing those early hits like “Delta Dawn” and learning about her personal battles with drugs and alcohol gave me a greater appreciation for the lived-in qualities of her voice.  

Here are two Tanya Tucker songs that capture the ‘90s energy I love and the early grit I grew into. 

“Down to My Last Teardrop” 

From her 1991 album What Do I Do with Me. Written by Paul Davis. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

My buddies who sang “Two Sparrows in a Hurricane” to get on my nerves didn’t know I had this album in my collection, but it was one of the first cassettes I bought as a true country fan. This song shows Tanya’s vocal range and humor. The echo of her background vocalists on “baby” and “honey” add dimension, and there’s just enough gravel in her voice to make the song instantly recognizable. 

“What’s Your Mama’s Name” 

From her 1973 album of the same name. Written by Dallas Frazier and Earl Montgomery. No. 1 on the Billboard Hot Country Songs chart. 

Like her debut hit “Delta Dawn,” this song’s content was controversial coming from a teenager. But even at 15, Tanya’s voice was as developed as any adult on the radio. I was in my 20s when “What’s Your Mama’s Name” pulled the rug out from under me with the revelation that the “drunkard” asking a child for her mother’s name isn’t out to abduct her. He’s simply looking for his lost daughter — the one her mama disclosed to him in a letter. It’s pure country gold and difficult to imagine any other voice gracing it. 

Shania Twain 

One of the biggest differences between young me and now me isn’t the strength of my opinions but the respect for how subjective music is. So when I say I’m not a Shania Twain fan, I mean no disrespect. I appreciate her place in country music history and admire the big swings she took to take control of her career early on. 

But I liked her first two singles — the ones even her biggest fans may not remember. “What Made You Say That” and “Dance with the One That Brought You” had a breezy, straight-forward charm that blended into the early ‘90s country landscape. Blending in, however, wasn’t Shania’s intention. She recalibrated and released her second album, The Woman in Me, in 1995. 

The album paired her with then-husband Mutt Lange as producer. He added modern pop and rock elements to her still-country vocals, giving her a swagger that appealed to both men and women. It was massively successful and influenced the sound of contemporary country music, helping pave the way for Taylor Swift and Kelsea Ballerini.  

For traditional country fans and critics, Shania’s new look — sexier with a bare midriff in her now iconic “Any Man of Mine” music video — was more controversial than her sound. I didn’t care about that; I just wanted to hear songs that told compelling stories.  

Don’t get me wrong. Not every song has to be a story. I still enjoy singing along to “You Win My Love,” but Shania invested in more bops than ballads in The Woman in Me and Come on Over. The Shania songs I prefer trade in some of the shimmer for a rootsier feel. Here are two examples of Shania finding that sweet spot. 

“No One Needs to Know” 

From her 1996 album The Woman in Me. Written by Robert John “Mutt” Lange and Shania Twain. No. 1 on the Billboard Hot Country Songs chart. 

This song was also included in the 1996 summer blockbuster Twister and on the soundtrack. It’s an infectious number that features harmonica and acoustic guitars, making it lighter than her rock-infused songs. And it still sounds fresh today, while “That Don’t Impress Me Much” and “Man! I Feel Like a Woman” are largely products of their time. 

“You’re Still the One” 

From her 1997 album Come on Over. Written by Robert John “Mutt” Lange and Shania Twain. No. 1 on the Billboard Hot Country Songs chart. 

I liked this pop-country ballad when she released it in ‘98, first to pop radio and then to country. What cements its timelessness for me is Harry Styles bringing out Kacey Musgraves to sing it with him in Nashville, which I’ve watched on YouTube. The pairing of the British pop star and alt-country favorite speaks to Shania’s crossover appeal and global success. 

Toby Keith 

Toby Keith is one of those rare artists who struck it big on his first try, taking his 1993 debut single, “Should’ve Been a Cowboy,” to the top of the charts. I loved that song, and so many of the ones that followed kept me hooked. 

“Wish I Didn’t Know Now” and “Who’s That Man” stuck to the neotraditional country format, with steel guitar, a little bit of twang, and storytelling lyrics, while “You Ain’t Much Fun” and “Big Ol’ Truck” showed Toby’s personality. 

When I was a kid, my grandparents’ house was as familiar as my own, and Grandmother always told me to make myself at home, even when they weren’t there. I’d ride my bike over, grab a Little Debbie, pour a glass of sweet tea, and watch their satellite TV until I heard her pull into the carport. 

I’d run to the kitchen door to greet her. Once, just as I opened the door, I caught Grandmother coming around the driver’s side singing, “You ain’t much fun since I quit drinking.” My grandmother was a teetotaler, so hearing that line come out of her mouth was especially funny. 

She just grinned at me. “You Ain’t Much Fun” was infectious and hit the right notes of humor for both of us. 

Toby pivoted from that softer humor to his “big dog” persona in 1999 and into the 2000s. “I Wanna Talk About Me” was Toby’s seventh No. 1, and “Courtesy of the Red, White and Blue (The Angry American)” extended that streak. While many fans gravitated towards his patriotic, bar-happy songs, his later work left me behind. 

Here are two Toby Keith songs that illustrate his evolution as an artist. 

“Who’s That Man” 

From his 1994 album Boomtown. Written by Toby Keith. No. 1 on the Billboard Hot Country Songs Chart. 

This is Toby Keith at his early-’90s finest, weaving snapshots of everyday life — the old hotel, the road the county finally fixed, the tree planted out by the fence — into a heart-breaking story about a divorced man surveying his losses. And the worst part isn’t just that he’s driving by his old house where his ex-wife and kids still live, it’s the question at the end of the chorus: “But who’s that man runnin’ my life?” 

“As Good as I Once Was” 

From his 2005 album Honkytonk University. Written by Toby Keith and Scotty Emerick. No. 1 on the Billboard Hot Country Songs chart. 

I know it’s meant to be a playful song about a man coming to terms with his age while talking to younger women in a bar, but it comes across a little skeezy to me. Obviously, fans heard the fun in it, keeping it at No. 1 for six straight weeks. 

Kenny Chesney 

Kenny Chesney started his career in 1993 as a George Strait devotee, wearing a cowboy hat and boots while singing about love and lessons learned. The first sign of the island guy we know today was 1998’s “How Forever Feels” and the music video that saw him singing shoeless and shirtless on the beach. 

It was Kenny’s second No. 1 hit and helped change the course of his career, inspiring him to add more Jimmy Buffet influences into his core country sound. While he continued to give us songs like “The Good Stuff” and “Don’t Blink,” Kenny transformed himself into a bankable star who sold out stadiums across the country with arena hits like “Beer in Mexico” and “Out Last Night.” 

And as his sound shifted, his look did too. Kenny put in countless hours at the gym, showed off his biceps in sleeveless shirts, and traded his cattleman for a palm straw with a surfer curve. Fans loved his “coastal country,” making his tours some of the biggest in country music history. 

But the poet-and-pirate persona didn’t appeal to me, and I ignored a lot of Kenny’s music from the mid-2000s on. Or at least I thought I did. Surveying his singles discography now, I realize that Kenny still cut songs that spoke to me. I was just more selective, choosing “You and Tequila” over “Pirate Flag.” 

Like Alison Krauss, Kenny deserves a full blog to understand his career pivot, so for now, here’s an example of how Kenny captured a radio-friendly and arena-heavy sound in one single. 

“Living in Fast Forward” 

From his 2005 album The Road and the Radio. Written by David Lee Murphy and Rivers Rutherford. No. 1 on the Billboard Hot Country Songs chart. 

Artists are at their best when they’re singing songs we can believe, and Kenny is no different. “Hillbilly rock star out of control” may be the single best description of his assent to the top. While Kenny didn’t write that line, he lived it, and fans eagerly sang along. 

The music we grow up with often transports us to nostalgia-laden “good old days,” but a little reflection reveals how much we’ve changed. I’d love to hear your stories of rediscovery. Which artists or songs sound different to you now? Share them in the comments. 

I didn’t know The Judds’ music until I knew they were walking away from it. 

Garth and Reba had just introduced me to a new kind of country — a twang different from what my dad played — when Naomi and Wynonna Judd told the world that Naomi’s devastating hepatitis C diagnosis was forcing her into early retirement. Whether I watched their press conference live on the news or in countless retrospectives since, those images are burned into my brain. 

Wy sat stunned, gripping her mother’s hand as Naomi dabbed at her eyes with a tissue. There was a tremor in her voice as she tearfully explained the Judds’ music wasn’t the only thing at stake. Naomi’s life was in jeopardy. 

It wasn’t the last time the Judds — known for their strength, resilience and abiding faith in God — would wield their vulnerability like a superpower. On the mountaintops of professional success and in the valleys of personal tragedy, the Judds endeared fans with grit and grace that’s woven through their music. 

Like so many of my favorite ‘90s artists, I started the Book of Wynonna in the middle. She was already one of the most unmistakable voices in country music when her 1992 solo debut rocked me in my boots. Without forsaking her acoustic roots, Wy broke new ground with a fresh sound that folded in glossy keyboards, electric guitars and more pop influences. 

Producer Tony Brown — who was shaping the decade alongside Vince Gill, George Strait, and Reba — gave Wynonna even more space to explore her raw vocal power and astonishing range.  

The woman-child with Elvis Presley swagger and Tammy Wynette ache was eager to step into her own spotlight. And as established Judds’ fans embraced Wy’s next chapter, her voice — with its shades of country, rockabilly, gospel, and the blues — became my gateway to one of the most successful duos in country music history. 

My Top 5 Wynonna Songs 

“Only Love” 

From her 1993 album Tell Me Why. Written by Roger Murrah and Marcus Hummon. Peaked at No. 3 on the Billboard Hot Country Songs chart. 

Listen, I could include the entire Tell Me Why album on my list and call it a day. It didn’t have the same commercial success as her solo debut, but only because that record set the bar so high. I love the acoustic guitar intro, the soft arrangement, and the intimacy of Wynonna’s voice — how it rises to a church-choir solo on the bridge — on this song. 

“Is It Over Yet” 

From her 1993 album Tell Me Why. Written by Billy Kirsch. Peaked at No. 6 on the Billboard Hot Country Songs chart. 

Packed with raw emotion and that throaty delivery, Wynonna skillfully balances quiet devastation with wracked regret. Vocally, I think this is her best performance. There’s a live version — one that ends in a standing ovation from her peers — that I’ll include on my YouTube playlist. It’s Wynonna at her most exposed and most commanding. 

“No One Else on Earth” 

From her 1992 album Wynonna. Written by Jill Coluccia, Stewart Harris, and Sam Lorber. No. 1 on the Billboard Hot Country Songs chart. 

Her third solo single followed “She Is His Only Need” and “I Saw the Light,” two songs that could have easily been Judds hits. But “No One Else on Earth” was something new. With its horn‑like intro and killer electric guitar riff, it has a big‑band swagger distinct from her earlier recordings. There’s a “Burning Love” edge to it — a sense that Wynonna has found her voice and is done wading into her solo career. She’s plunging in headfirst. 

“Girls with Guitars” 

From her 1993 album Tell Me Why. Written by Mary Chapin Carpenter. Peaked at No. 10 on the Billboard Hot Country Songs chart. 

Skip the liner notes and you’d swear Wynonna wrote this anthem about a young girl’s rock ‘n’ roll dreams. Her parents buy her a guitar, hoping it’s a phase — but their baby girl’s in it for the long haul. My favorite image is when she “gives a little grin and blows away the jerk,” which Wy delivers with a smirk you can hear. Lyle Lovett and Naomi join her on the chorus in what I can only imagine was a joyful day in the studio. 

“Testify to Love” 

From 1998’s Touched by an Angel: The Album. Written by Paul Field, Henk Pool, Robert Riekerk, and Ralph Van Manen.  

Originally recorded by contemporary Christian group Avalon, Wynonna’s cover appears on a compilation that peaked at No. 3 on both the Billboard Top Christian Albums and Top Country Albums chart. Mom and I watched Touched by an Angel after church on Sunday nights, and she bought me the CD soundtrack. “Testify to Love” quickly became a favorite — the simple acoustic opening, the wide-open vocals, the gospel lift. I still get chills hearing it. 

My Top 5 Judds Songs 

“Love Is Alive” 

From their 1984 Why Not Me album. Written by Kent Robbins. No. 1 on the Billboard Hot Country Songs chart. 

Those early Judds’ records are marked by their simplicity — simple instrumentation and simple arrangements — but Wynonna and Naomi add layers with their high, ringing harmonies and soulful phrasing. They turn “simple” songs like “Love Is Alive” into timeless classics.  

“Rockin’ with the Rhythm of the Rain” 

From their 1985 album of the same name. Written by Brent Maher and Don Schlitz. No. 1 on the Billboard Hot Country Songs chart. 

A joyful, jubilant ode to love, with the Judds inviting us onto that front porch swing. I love the call-and-response chorus, the steady backbeat, and that opening acoustic guitar riff. It’s modern and rootsy all at once — the Judds at their most effortless and effervescent. 

“Born to Be Blue” 

From their 1990 album Love Can Build a Bridge. Written by Brent Maher, Mike Reid, and Mack David. Peaked at No. 5 on the Hot Country Songs chart. 

Wynonna gets wild on this one, and I’m for it. That growl in her voice — that bluesy bite — is a clear precursor to her solo work. You can hear her stretching out, testing the edges of her range, and leaning into that rockabilly swagger that would define her 1992 debut. 

“Grandpa (Tell Me ‘Bout the Good Old Days)” 

From their 1985 album Rockin’ with the Rhythm of the Rain. Written by Jamie O’Hara. No. 1 on the Billboard Hot Country Songs chart. 

I know I’m not the only sucker for nostalgia because fans still cling to this touching portrait of families gathered around the supper table. The Judds aren’t just singing a song — they’re pleading for a renewal of relationships, promises, and faith. Their fervent hope echoes down through the decades and still lands with the same pining. 

“Why Not Me” 

From their 1984 album of the same name. Written by Harlan Howard, Brent Maher, and Sonny Throckmorton. No. 1 on the Billboard Hot Country Songs chart. 

When you see Harlan Howard’s name in the credits, you know you’ve got a well-crafted song. The legendary songwriter preferred simple, emotionally honest lyrics that created a conversation between the singer and listener. The Judds interpreted “Why Not Me” with warmth, balancing flirtation with longing — Wynonna’s rich lead and Naomi’s bright harmony creating that unmistakable Judds shimmer. 

Life beyond the music 

I don’t usually delve into the personal lives of the artists I write about. I don’t know these people, not really. I think I know some of them — or at least the versions they’ve shared with the public — but it’s hard to separate the person from the image. With the Judds, that line feels even thinner. 

But I can’t write about Wynonna and Naomi without discussing their humanity — the childhood abuse, the generational trauma, the battles with mental illness — so going beyond their music feels necessary. 

On stage, the Judds were a perfect match — Naomi with her frilly dresses and high heels, playfully working the crowd while Wynonna embraced a more tailored style and stood grounded at the mic stand with her guitar. They told jokes, talked about their musical “heroes and sheroes,” and racked up 14 No. 1 hits. 

They were darlings of the industry, with five Grammy Awards, eight ACMs, and nine CMAs. 

How were we to know what was going on behind the scenes? It would take years of therapy to confront their reality — and courage to share it with the world. Along with daughter/sister Ashley, the Judds put on that heavy mantle of responsibility. 

They were no longer aspirational; they were relatable. I don’t know what it’s like to hear my name called at the Grammys. I don’t have the means to buy anything or go anywhere I want, and nobody’s asking for my autograph. 

But I know the burden of self-doubt. I know depression is a liar. I know grief. And so do you. 

When the Judds — in their seemingly carefree existence, didn’t just let their masks slip but willingly took them off for the world to see — people took notice. Oprah Winfrey hosted them on her eponymous talk show a combined 18 times, and her OWN network aired Wynonna and Naomi’s 2011 docuseries The Judds. 

The Judds probed the complex and at times strained relationship beneath Wy’s wry observation, “If it’s not one thing, it’s your mother.” These women were hurting, and the road to reconciliation and healing for all three Judds would be long and arduous.  

In 2012, I won tickets to a live taping of the first episode of Naomi’s limited-run talk show on SiriusXM. Before the show, I bumped into her leaving her hotel and summoned the courage to say hello. 

Her smile lit up her face and mine, and we shared a brief but warm conversation. She asked my name, my hometown — taking an interest in me that felt genuine. I walked away completely charmed. 

After the show, we met again “backstage” where SiriusXM had a photographer. Before posing for a photo, she asked me how she did and waited, almost nervously, for my answer. 

Seriously. 

After selling 20 million records, Naomi Judd looked to me — a stranger — for validation. That moment didn’t fully sink in until 2022, when she died by suicide the night before she and Wynonna were to be inducted into the Country Music Hall of Fame. 

On the precipice of the ultimate professional validation, Naomi was fighting a darkness deeper than her stardom could shine. Her adoring public wept with her family and friends in a moving memorial service televised from the Ryman Auditorium.  

Her daughters and husband are still letting us in — through 2023’s Wynonna Judd: Between Hell and Hallelujah and 2025’s The Judd Family: Truth Be Told — as they reckon with their grief and search for hope in their heartache. 

When the Judds burst on the scene in 1983, they were a breath of fresh mountain air in the crossover-friendly world of country music. They sounded like perfection, but their lives were far from it. They sang through the hard parts — and helped us feel less alone in our own struggles. That’s their legacy. 

And Wynonna — still touring and bringing audiences to their feet — keeps pushing the boundaries of country music while finding solace in her mother’s melodies and memories. 

When Patty Loveless had a big hit with “Blame It on Your Heart” in 1993, I was in middle school and just starting to fall in love with country music. With its fiddle, steel guitar, and tongue-twisting chorus, the song was an early favorite of mine. I couldn’t help but tap my toes and sing along. 

But when I bought Only What I Feel, I realized Patty’s voice held something deeper — a sound that carried both hope and heartache. I didn’t have the language for it then, but I know it now: she sings with the voice of a sorrowful angel. 

That sound was forged in the Appalachian Mountains where Patty Loveless traces her lineage. With its rich traditions of storytelling, string bands, and ethereal harmonies, mountain music is a cornerstone of country music. And Patty is a direct descendant of a line of its most influential practitioners — the Carter Family and Ralph Stanley, Loretta Lynn and Dolly Parton. 

With Appalachia always present in her music, Patty’s voice rises to the heavens while carrying the weight of Eastern Kentucky’s coal mines in every note. Never do her roots shine brighter than in her late-career Mountain Soul and bluegrass projects that helped draw a new generation of fans to her homeland. 

For this installment of Roots & Rhinestones, I’ll break down Patty’s career from her time with MCA before she underwent vocal surgery and her comeback and tenure with Epic. 

The MCA years 

Though I was unaware of Marty Stuart’s sage advice to start with what you like in country music and work your way back, that’s exactly what I did with Patty Loveless. Her Greatest Hits album — with songs like “If My Heart Had Windows” and “Don’t Toss Us Away” — was revelatory.  

Before Patty, I wasn’t a fan of the traditional country singers she loved. I couldn’t appreciate George Jones or Porter Wagoner because I thought their tones were too nasal. It didn’t happen overnight, but Patty was a bridge that helped me hear the emotion in those stone-cold country voices. 

Those traditional influences came alive on her MCA albums thanks to the musicians who surrounded her — Tony Brown, Paul Franklin, Mark O’Connor, Eddie Bayers, and her future husband Emory Gordy, Jr. With talent like that behind her, the final piece was finding songs worthy of her emotional range. 

From the start, Patty showed a knack for selecting songs that fit her voice and Appalachian roots. She worked with some of the era’s finest songwriters — Kostas, Matraca Berg, and Tony Arata — while going back in time to cover Hank Williams and Carter Stanley. 

Kostas penned Patty’s first No. 1 single and breakout hit “Timber, I’m Falling in Love,” which featured Vince Gill on background vocals. Fiddle and steel guitar drive the melody, with Patty and Vince riding the chorus upward to mirror the joy of falling in love. 

Patty continued adding to her catalog of hits with her next two albums. But in 1992, doctors found an aneurysm on one of her vocal cords. Surgery to remove it was successful, and she followed it with vocal rest and therapy. The break came just as she was hitting her stride, but praise the Lord, Patty returned with an even stronger voice. She stepped into the next chapter of her career with a new label — and a voice ready to cement her place as one of country music’s most expressive storytellers. 

Epic Records 

1993’s Only What I Feel was her first album on her new label. Critics and fans immediately noticed the change in her voice. There was a new intensity — a richer, warmer tone and bigger range that allowed her to take on some of her most demanding material. 

And at the center of this new chapter was her husband Emory Gordy, Jr. who produced her Epic albums and helped shape the sound that defined her greatest work. In 1995, they took home trophies for CMA Album of the Year for When Fallen Angels Fly. Patty was only the second solo female artist to win the coveted award. That partnership would prove to be, well, epic. 

For my money, When Fallen Angels Fly is her best work. Singles “Here I Am” and “You Don’t Even Know Who I Am” belong in the same conversation as country standards — songs that define eras and outlast trends. Patty delivers a master class in storytelling, her voice breaking in all the right places to convey heartbreak and resignation.  

Patty followed When Fallen Angels Fly with The Trouble with the Truth, scoring her third consecutive platinum-selling album. By the late ’90s as the genre trended toward pop influences, Patty’s chart success was spotty. Her fans, however, stuck with her. 

In 2001, she released her masterpiece — Mountain Soul. 

I’m no expert, but I understand the music business can be heavier on the business than the music. Producers, entertainers, label executives — everybody’s got to make a living. So I love when someone of Patty’s stature says, “I’ve sold lots of records for you. Now I’m going to make the album I want to make.” 

Mountain Soul peaked at No. 19 on the Billboard Top Country Albums chart and was hailed by critics, but there wasn’t a place for it on country radio. Singles “The Boys Are Back in Town” and “Out of Control Raging Fire” didn’t chart, but Patty Loveless had come home.  

All 14 tracks are steeped in the Appalachian sound that shaped her — fiddle, mandolin, tight harmonies, and that unmistakable high‑lonesome ache in her voice. And with friends Ricky Skaggs, Earl Scruggs, Stuart Duncan, Jon Randall, Rebecca Lynn Howard, and Travis Tritt lending their impressive talents to the record, Patty created more than an album. Mountain Soul is a celebration of community —  a front-porch jam session — making it my favorite in her discography. 

She followed it with Bluegrass and White Snow: A Mountain Christmas — the holiday version of the jam session — and later gave us Mountain Soul II. In 2008, Patty released Sleepless Nights, billed as “The Traditional Country Soul of Patty Loveless,” covering country standards like “Crazy Arms,” “There Stands the Glass,” and “Cold, Cold Heart.” 

Patty hasn’t recorded new music since 2009, largely retiring from the spotlight to care for her husband. She occasionally performs on the Grand Ole Opry, and she took her rightful spot in the Country Music Hall of Fame in 2023.  

In 2022, Patty surprised fans at Chris Stapleton’s Kentucky Rising benefit concert, which raised money for victims of that summer’s Eastern Kentucky floods. Those Kentucky mountain voices created pure magic that night, which is nothing new for Patty. She’s been backing her peers since her arrival in Nashville in the ‘80s. 

It was tempting to stretch my Top 5 Patty Loveless songs into a Top 10. Her catalog is deep, and she doesn’t waste a single release. But in the spirit of Roots & Rhinestones — and because Patty has always shined when she’s lifting others up — I’m starting with a twist. Before giving her the solo spotlight, here are my Top 5 Patty Loveless collaborations. 

“When I Call Your Name” by Vince Gill 

From Vince’s 1989 album of the same name. Written by Vince Gill and Tim Dubois. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

Vince has compared himself and Patty to George Jones and Melba Montgomery, calling it a “special anointing.” They had the privilege of working on each other’s breakout hits, with Patty providing background vocals on his “When I Call Your Name.” There are a lot of great harmony singers in Nashville, but it’s hard to imagine anyone but Patty on that record. 

In 1995, Patty and Ricky Skaggs joined Vince on “Go Rest High on That Mountain.” Thirty years later, fans are still connecting with Vince’s poignant tribute to his late friend Keith Whitley and late brother Bob. The song was destined to be a classic, but Patty and Ricky helped lift those words to heavenly heights. 

“Please Remember Me” by Tim McGraw 

From Tim’s 1999 album A Place in the Sun. Written by Rodney Crowell and Will Jennings. No. 1 on the Billboard Hot Country Songs chart. 

Tim has always walked the line between “Indian Outlaw” and “It’s Your Love,” making him a compelling artist. Put “Please Remember Me” in the emotionally mature column of his hits. His performance deserves every accolade he received — including a Grammy nomination — but Patty’s gentle ache on background vocals turns the song into something timeless. 

“You Don’t Seem to Miss Me” with George Jones 

From Patty’s 1997 album Long Stretch of Lonesome. Written by Jim Lauderdale. Peaked at No. 14 on the Billboard Hot Country Songs chart. 

It’s not a cover of a Jones hit, but Patty sure makes it sound that way. Adding him on background vocals was an inspired choice that gives it that early honky-tonk vibe from her MCA years. Their voices — his pure hillbilly and hers refined coal — blend with a shared lived‑in quality that takes the song from heard to felt. 

“Bible and a .44” by Trisha Yearwood 

From Trisha’s 2019 album Every Girl. Written by Terri Jo Box, Ashley McBryde, and Patrick Savage. 

How could I not put a song featuring two of my all-time favorites on the list? It was never released as a single, but the song pays tribute to a dad who taught his daughter everything from how to hunt to how to praise the Lord. Trisha’s performance is restrained, pulling back that big voice to create the intimacy the song deserves. And Patty’s background vocals feel like burying your face in Dad’s old shirt — hints of sweat, Old Spice, and comfort filling your nostrils and your memories. 

“Dear Diamond” by Miranda Lambert 

From Miranda’s 2011 album Four the Record. Written by Miranda Lambert. 

Patty didn’t just put down the harmony track for Miranda Lambert’s “Dear Diamond,” her signature sound inspired Miranda to write it. The gem Miranda describes is a “perfectly flawless” ring, and it’s tempting to apply that to Patty Loveless. But the “flaws” in her voice — that tension between clinging coal dust and refreshing mountain air — wrap me around her finger tighter than any wedding band. Kudos to Miranda for capturing Patty’s essence in this heartbreaker, which, unfortunately, wasn’t released as a single. 

This has, hands down, been the most challenging Top 5 I’ve put together for Roots & Rhinestones. Patty’s catalog spans more than 40 years, so narrowing her hits wasn’t easy. These five stand out as moments where her voice carries the story as only she can. 

My Top 5 Patty Loveless Songs 

1. “On Your Way Home” 

From her 2003 album of the same name. Written by Ronnie Samoset and Matraca Berg. Peaked at No. 29 on the Billboard Hot Country Songs chart. 

2003 was a time of transition as ‘90s heavyweights shared the charts with the next generation of country stars. “Bro country was still on the horizon, but the neotraditional sound was moving toward more pop-country. Maybe that’s why this haunting song didn’t get the attention it deserved. The somber fiddle intro sets the scene for another story of betrayal. But this time, the woman at its center is willing to stay — if only to spite the man who won’t tell her the truth. 

2. “Here I Am” 

From her 1994 album When Fallen Angels Fly. Written by Tony Arata. Peaked at No. 4 on the Billboard Hot Country Songs chart. 

The devil himself officiated the wedding between liquor and heartache, but country music hosted the reception. In this single, the brokenhearted lover is branded by bourbon and water and lies. Patty soars on the bridge, her voice breaking under the weight of the emotion she’s carrying. It is both classic ‘90s country and classic Patty Loveless. 

3. “Hurt Me Bad (In a Real Good Way)” 

From her 1991 album Up Against My Heart. Written by Deborah Allen and Rafe Van Hoy. Peaked at No. 3 on the Hot Country Songs chart. 

Patty delivers a tender performance on this sweet song of gratitude to the lover who hurt her — because he led her straight to a new and devoted love. 

4. “A Thousand Times a Day” 

From her 1996 album The Trouble with the Truth. Written by Gary Burr and Gary Nicholson. Peaked at No. 13 on the Hot Country Songs chart. 

Here’s another Patty song with a mournful fiddle, and she matches it by pulling back and belting in all the right places. And what a clever hook — “Forgetting you is not that hard to do/ I’ve done it a thousand times a day.” 

5. “The Last Thing on My Mind” 

From her 2000 album Strong Heart. Written by Craig Wiseman and Al Anderson. Peaked at No. 20 on the Billboard Hot Country Songs chart. 

If Patty’s delivery isn’t enough to move you, the lyrics — full of Wiseman’s wit and irony — will. My absolute favorite line is so out of left field that it stops me cold every time: “And this empty bed’s as big as Arkansas.” 

Bonus Album Cuts 

“You’ll Never Leave Harlan Alive” 

From her 2001 album Mountain Soul. Written by Darrell Scott. 

I could do a whole blog on this song alone. It feels autobiographical for good reason. Patty, like her distant cousin Loretta Lynn, is a coal miner’s daughter. She does, in fact, trace her bloodlines to those “deep, dark hills of Eastern Kentucky,” where for generations, broken promises from outsiders meant the same ending: “Spend your life diggin’ coal from the bottom of your grave.” Tear my heart out, why don’t you? 

“A Handful of Dust” 

From her 1994 album When Fallen Angels Fly and her 2009 album Mountain Soul II. Written by Tony Arata. 

I love the simplicity of this one — a song Patty gives the bluegrass treatment in her second recording of it. It’s a gospel message of love without a hint of preachiness. 

“Someday I Will Lead the Parade” 

From her 1996 album The Trouble with the Truth. Written by Tony Arata and D. Scott Miller. 

As a writer, it’s frustrating when I can’t find the words to express my feelings. Unfortunately, the problem plagued me long before I knew I wanted to earn a living in communications. I remember trying to tell a high school friend how Patty ended her albums with these special tracks that always left me feeling a little melancholy. “Someday I Will Lead the Parade” — the closer on this album — could have been taken straight out of The Baptist Hymnal and sung at every church homecoming and funeral. 

I went a few rounds with this blog. Patty’s singular voice is like art — I don’t know how to define it, but I know it when I hear it. I hope you enjoy the included playlists. The Amazon Music version includes Josh Turner’s cover of “You Don’t Seem to Miss Me” and Brad Paisley’s “You’ll Never Leave Harlan Alive.” Make sure to add your own favorites and share them in the comments. We’ll stay in Kentucky for our next installment and follow Wynonna from her time with mom Naomi in The Judds to her solo career. 

As always, thanks for reading! 

Travis Tritt

My parents have never tolerated vulgar language. When I was a kid, I allegedly asked my oldest brother what the hell he was doing, prompting our mom to send me to timeout under the kitchen table. While I don’t remember the incident, I’m certain I didn’t hear that phrase at home. 

So when Travis Tritt released “Here’s a Quarter (Call Someone Who Cares)” in 1992, I was uncomfortable with the chorus. But Travis’s smirking delivery and the song’s infectious melody made it difficult for me not to sing along. For years, I changed “damn” to “darn” — an edit I felt was acceptable but probably wouldn’t have met Travis’s standards as the songwriter or singer. 

After all, the B-side of that single is “If Hell Had a Jukebox,” a song that wouldn’t have been admired in my house no matter how many changes I made. 

Now, when I think about Travis Tritt, my first thought is “T-R-O-U-B-L-E,” a song that fits both his swagger and energy. In a musical cohort that includes Clint Black, Garth Brooks, and Alan Jackson, Travis stands out for embracing the neotraditional sound while defying the Nashville establishment. 

During the height of “Achy Breaky Heart” mania, Billy Ray Cyrus slammed a quarter down on the podium. It happened at the 1993 American Music Awards, where Motley Crue had just presented him with the trophy for Best Country Song. Billy Ray told anyone who didn’t like his smash hit to “call someone who cares.” 

Call it a lapse in judgment or a moment of candor. Travis had, after all, publicly criticized the song. He later apologized, and he and Billy Ray went on to honor a shared hero — Waylon Jennings — on stage together. 

Burying the hatchet showed Travis’s maturity, just as his tender love songs and soulful ballads do. Much more than a good-timin’ man, Travis is a gifted songwriter with a rich voice that carries the dreams of the working class, a creative eye for music videos, and a genuine connection to his fans.  

For the final entry in my Class of ‘89 series, let’s look at Travis’s distinctive catalog of hits — while also unpacking some of his most memorable music videos. 

Bulletproof 

Travis released his debut studio album, Country Club, in 1990. The album produced five bona fide hits, including his first No. 1 single. All of them showed the emotional and stylistic range of his songwriting and vocal delivery. 

Travis gives “Country Club,” written by Catesby Jones and Dennis Lord, a breezy feel that allows fans to sink into the deliciously clever lyrics. While the self-penned “Put Some Drive in Your Country” takes listeners on a ride through Travis’s musical influences, it also effectively maps out his career. “Drift Off to Dream,” which he cowrote with Stewart Harris, captures the tenderness of a sweet, private moment. 

Throughout his career, Travis’s songs have run the gamut from sly and sexy to mournful and introspective. His voice holds his memories of George Jones, Lynyrd Skynyrd, and Sam Moore. His gritty, rootsy delivery — with its underlying warmth — draws listeners in. It’s no surprise that the more you hear from Travis, the more you want to hear. 

That blend is crucial to Travis’s success. The invincibility of “Ten Feet Tall and Bulletproof” is nothing without the vulnerability of “Can I Trust You with My Heart.” 

He’s a masterful storyteller, mining the ups and downs of his own life to create compelling songs that resonate with fans. He co-wrote his first three No. 1 hits — all of them ballads — but like George Strait and Reba, he can find songs from other songwriters that fit him like a glove.  

“Lord Have Mercy on the Working Man,” written by Kostas, is a blue-collar anthem Travis sings with gusto that comes from having lived it. “Modern Day Bonnie and Clyde,” written by Walt Aldridge and James LeBlanc, has all the hallmarks of a great Travis Tritt story with a swampy sound that gives it an extra edge. 

Travis’s willingness to wear his heart on his sleeve gives his catalog a seamless quality. Each song is a new chapter of the same book — with Travis’s fans hanging on every word. 

Trilogy 

Like many of his peers in the ‘90s, Travis understood the power of the music video and used the medium to great success. But he was the first to carry a single character through a cohesive storyline in a series of powerful videos. What makes this trilogy remarkable is that it wasn’t planned — the story simply kept unfolding over seven years. 

It started with 1991’s “Anymore,” directed by Jack Cole. In a bold move, Travis plays a disabled Vietnam veteran named Mac Singleton. Scenes from a VA hospital where Mac is receiving physical therapy are interspersed with his memories of his wife Annie. The video could have easily crossed into cheesy or comically overdone territory, but Travis’s portrayal of Mac is sincere and his reunion with Annie feels genuine. 

Then in 1995, four years after “Anymore,” Travis and director Michael Merriman gave Mac an unexpected sequel with “Tell Me I Was Dreaming.” Barry Scott reprises his role as Al, Mac’s fellow veteran and steadfast companion. Annie, unfortunately, doesn’t get a happy ending in this one. She falls and hits her head on the docks, leaving Mac a widower with an infant daughter. It was bleak, but revealing the couple’s baby girl at least gave viewers a glimpse of joy. 

Merriman returned to direct 1998’s “If I Lost You,” the final chapter arriving seven years after Mac first appeared on screen. The video opens with the ending of “Tell Me I Was Dreaming” before jumping five years into the future to show Mac with his little girl. Al is still by his side, helping Mac and his daughter. In the closing minute, we see daddy and daughter visit Annie’s memorial, ending the trilogy on a bittersweet note of sorrow and hope. 

Those videos aren’t the only heavy ones in Travis’s arsenal, but he has some light-hearted entries too. One of my favorites is 1996’s “More Than You’ll Ever Know,” directed by John Lloyd Miller. Travis gets into character once again, playing an old man “collecting” flowers from his neighbors’ gardens to fill his wife’s hospital room. His makeup and costume are so good, I didn’t realize the old fella was Travis the first few times I saw the video. 

If you think of songs as stories and stories as connections, you’ll see how Travis built a dedicated fan base over his 30-plus years in the business. I saw that connection firsthand several years ago at the Discovery Park of America’s outdoor summer concert series. Let me say, there were some women congregated near the stage who were very excited to see Travis Tritt. 

He did several of his big hits with his band before sending them off and finishing the set with just his acoustic guitar. He was equally engaging in both settings, and I was delighted to recall all those great songs from the ‘90s and early 2000s that made Travis Tritt one of the most influential artists of his generation. 

Whittling down my list of Travis Tritt songs to just my top five favorites was no small task, but I hope each one inspires you to dig deeper into his catalog. 

My Top 5 Travis Tritt Songs 

“It’s a Great Day to Be Alive” 

From his 2000 album Down the Road I Go. Written by Darrell Scott. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

Picture a perfect spring day with clear skies and the sun shining brightly. The windows are down, and you’re driving your favorite stretch of country road. Put on this song, crank it up and let Travis take you to church. I know it’s not a gospel song, but I feel like I’m praising the Lord with him every time this one comes on. 

“Where Corn Don’t Grow” 

From his 1996 album The Restless Kind. Written by Roger Murrah and Mark Alan Springer. Peaked at No. 6 on the Billboard Hot Country Songs chart. 

I remember thinking this song was lame when I first heard it in 1996. Just like the narrator, I thought I knew more than I did. Now, I understand that the weeds are indeed high “where corn don’t grow.” Travis’s voice is hauntingly similar to Waylon’s in this cover of a song his hero released just six years earlier. 

“Modern Day Bonnie and Clyde” 

From his 2000 album Down the Road I Go. Written by Walt Aldridge and James LeBlanc. Peaked at No. 8 on the Billboard Hot Country Songs chart. 

I’m a sucker for a song that features the great State of Tennessee, and this ride takes us to a truck stop in Johnson City where the narrator meets a woman who will get him in all sorts of trouble before their time together comes to an end. Travis gives a master class in his trademark country-rock-soul-infused rasp on this number. The accompanying music video perfectly casts Oscar winner Billy Bob Thorton as the modern-day Clyde. 

“Sometimes She Forgets” 

From his 1995 album Greatest Hits: From the Beginning. Written by Steve Earle. Peaked at No. 7 on the Billboard Hot Country Songs chart. 

When artists include new songs on a greatest hits package, you have to wonder if they’re manifesting another hit or setting themselves up for a letdown. “Sometimes She Forgets” was a smart move for Travis, who put an Eagles-inspired spin on it to create a piece of music that is distinct from any of his previous songs. It’s a simple story told simply. 

“The Whiskey Ain’t Workin” (duet with Marty Stuart) 

From his 1991 album It’s All About to Change. Written by Ronny Scaife and Marty Stuart. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

When this duet was released, Marty Stuart was making what he’s since called “butt-wigglin’” music — the kind that sells out stadiums now but may not match the longevity of the classics. But he and Ronny Scaife penned a country standard that still holds up today. Travis’s and Marty’s voices blend perfectly with an almost-familial harmony they replicated on 1992’s “This One’s Gonna Hurt You (For a Long, Long Time),” which Marty also wrote. 

And that’s a wrap on the Class of ‘89 series. I don’t think I had any of Travis’s albums, so I can’t give you any bonus album cuts. His singles should give you plenty of material to remember — or discover — the music that made ‘90s country so special. 

Below you’ll find the accompanying playlists featuring my top favorites from Clint, Garth, Alan, and Travis, with bonus album cuts from Clint, Garth and Alan. Since Garth doesn’t have an official YouTube channel, I didn’t include his music on that playlist.  

Remember to add your own favorites and share them in the comments. 

Alan Jackson

One middle school summer, my cousin Sarah and I caught a ride home with our Meme after the fireworks at our aunt’s Fourth of July pool party.

I climbed into the backseat of her Buick LeSabre while Sarah rode shotgun. On a country road, we sang Alan Jackson’s “Chattahoochee” at the top of our lungs, bickering over who had the lyrics right.

I’m not saying we didn’t deserve it, but Meme was awfully quick to blame our singing when a police officer pulled her over. Maybe that was a clue I’d never be a music star…or maybe we can chalk it up to Alan’s charm.

In the ‘90s, Clint Black was my favorite of the Class of ’89. But now I gravitate to Alan Jackson. His music also connects me to memories of my maternal grandmother and our special bond.

With the songwriting chops of a Don Williams or a Merle Haggard, and a voice that carries the legacy of George Jones, Alan Jackson moved country music forward while honoring its traditions.

In his 1985 hit “Who’s Gonna Fill Their Shoes” — written by Troy Seals and Max D. Barnes — George Jones asks who’s going to give their heart and soul to the music.Alan Jackson made it clear early in his career that he was one answer to the question, earning a place on the Mount Rushmore of ‘90s country icons.

Let’s dive into Alan’s place in the Class of ’89 — as the songwriter who paints vivid portraits of small towns and rural living, and as the artist who embraced the music video as part of his storytelling.

Small town, Southern writer

Like Clint Black, Garth Brooks, and Travis Tritt, Alan Jackson found early chart success with 1989’s No. 3 hit “Here in the Real World,” followed by his first No. 1 in 1990 with “I’d Love You All Over Again.”

As I review Alan’s catalog of hits, I’m struck by the variety. He writes as easily about family and home as he does about romance and heartbreak. With autobiographical songs like “Chasin’ That Neon Rainbow” and beautiful tributes like “Small Town Southern Man,” Alan tells his own stories while reflecting ours.

“Little Man” recounts my experience as a kid growing up in a small county with a once thriving county square. When I hear “Drive (For Daddy Gene),” I see my granddaddy letting me take the wheel of his fishing boat. And the chorus of “Small Town Southern Man” could be an ode to my dad.

Alan doesn’t just speak for a generation of fans — he speaks to us, capturing our shared experiences. Few songs illustrate that better than “Where Were You (When the World Stopped Turning),” the song Alan wrote after the 9-11 terrorist attacks in 2001. Moving in their simplicity, the lyrics make a place for everyone to feel seen and heard.

The question isn’t “How Did You Feel (When the World Stopped Turning).” Alan conveys the full range of emotion — shock, anger, fear, guilt, sorrow, and even pride.

Instead, he asks us what we were doing at that fateful moment — hanging out with family, working, teaching children, or driving — and more importantly what we did in the aftermath.

Pray? Give blood? Call Mama?

Like many of Alan’s hits, “Where Were You (When the World Stopped Turning)” uses plainspoken language to speak deep truths, separating the politics from the humanity of the tragedy.

It’s no wonder the song topped the country charts for five weeks and climbed to No. 28 on the all-genre Billboard Hot 100. I wouldn’t argue if you called it the crowning achievement of his Hall of Fame career.

But Alan’s songs are also marked by their cleverness, and I’m not just talking about the funny ones.

There are early hits “Don’t Rock the Jukebox” — about a brokenhearted man wanting to hear country instead of rock — and “Dallas” — about a woman named Dallas who lives in Texas, while he’s in Tennessee.

And later hits “Remember When” — a couple looking back on their relationship while also looking ahead — and two songs Alan didn’t write but match his style perfectly: “It’s Five O’Clock Somewhere” and “The Talkin’ Song Repair Blues.”

Through it all, Alan wove in music videos to visually enhance so many of his stories — including that song Meme blamed on that long-ago Fourth of July.

“Chattahoochee”

While Alan uses music videos to express some of his sincerest ballads, my favorites are the ones that showcase his personality. His humor shines through on early hits, but “Chattahoochee” took it to the next level.

Timed with the opening twin-lead guitar lick and fiddle playing in harmony, Alan — in his signature white cowboy hat and a life jacket — rises out of the water gripping a tow rope. The camera pulls back to reveal he’s water-skiing in ripped jeans. Later, he’s wearing cowboy boots as skis and using his guitar as an oar while he tubes.

Cut between scenes of teenagers awkwardly flirting and Alan and his band playing on a pier, it’s impossible to watch “Chattahoochee” without matching Alan’s wide grin. Decades later, it’s pure nostalgia for anyone who spent their summers at the lake or river.

He matches that carefree energy in “Summertime Blues” and “It’s Five O’Clock Somewhere.”

For a moment, picture country music as a relay race. George Jones grips the baton passed from Hank Williams. As he rounds the turn, he spots Alan Jackson — full of talent, creativity, authenticity, and reverence for the genre — ready for his leg, knowing the race won’t end with him. Alan will pass the baton to Brad Paisley, who, shaped by his predecessors, will chart a course for country music in the early 2000s.

Thanks in no small part to Alan Jackson, the circle of country music remains unbroken. While I could easily give you a playlist a mile long, I’ll stick to my format and share my Top 5 Alan Jackson songs — plus three bonus album cuts.

My Top 5 Alan Jackson Songs

“Dallas”

From his 1991 album Don’t Rock the Jukebox. Written by Alan Jackson and Keith Stegall. No. 1 on the Billboard Hot Country Songs chart.

Written with his frequent collaborator and producer, Keith Stegall, the wordplay in “Dallas” is simply delicious: I took her out of Texas/ When she was just a girl/ But old Tennessee and me/ Couldn’t take Texas out of her.

“Drive (For Daddy Gene)”

From his 2002 album Drive. Written by Alan Jackson. No. 1 on the Billboard Hot Country Songs chart.

A Billboard critic described the song as having “emotional warmth,” and I can’t think of a better way to put it. Even though this is Alan’s story about his grandfather, he fills it with such relatable imagery that fans of all ages and walks of life can wrap themselves in its glow.

“Gone Crazy”

From his 1998 album High Mileage. Written by Alan Jackson. Peaked at No. 4 on the Billboard Hot Country Songs chart.

Alan has a beautiful, clear, strong voice, and his slower ballads tend to show it off a bit more than his more up-tempo songs. On “Gone Crazy,” he infuses lyrics full of his signature wordplay with a longing and sorrow that give the listener pause. The stripped-down arrangement only deepens the ache in his voice.

“(Who Says) You Can’t Have It All”

From his 1992 album A Lot About Livin’ (And a Little ‘bout Love). Written by Alan Jackson and Jim McBride. Peaked at No. 4 on the Billboard Hot Country Songs chart.

Wearily proclaiming himself “lord and master of a fool’s Taj Mahal,” Alan stretches himself vocally on this one. He was named Top Male Vocalist or Male Vocalist of the Year by the ACMs and CMAs a combined five times, thanks to those golden pipes.

“Chasin’ That Neon Rainbow”

From his 1990 album Here in the Real World. Written by Alan Jackson and Jim McBride. Peaked at No. 2 on the Billboard Hot Country Songs chart.

Alan gives us a glimpse into his upbringing — both at home as a young boy and on the honky-tonk circuit as a young artist — in this infectious early hit that leans into the neotraditional country sound Alan typifies. Steel guitars, fiddles, and a beat built for a line dance make “Chasin’ That Neon Rainbow” a classic.

Bonus Album Cuts

“Precious Memories”

From his 2013 album Precious Memories Volume II. Written by John B.F. Wright.

In 2006, Alan made good on a promise to his mother and recorded his first gospel album, Precious Memories. My grandmother loved Alan Jackson and traditional hymns, and I often walked into her kitchen to hear that CD playing while she cooked or cleaned. When he released his second volume, I bought it for her.

Many years later, after Grandmother suffered a stroke, Mom would play Alan’s Precious Memories collections on her smartphone to soothe Grandmother during restless nights in the hospital. And when Grandmother passed away, we played his cover of “Precious Memories” at her funeral — just as she had done at Granddaddy’s a couple of years before.

If I ever meet Alan Jackson, I’ll give him a great, big hug for that.

“The Firefly’s Song”

From his 2006 album “Like Red on a Rose.” Written by Robert Lee Castleman.

Alan took a creative gamble in 2006 when he handed the reins of an entire album over to Alison Krauss. Not only did the bluegrass songstress produce the album, but she also chose every song. In fact, there’s only one Alan-penned number — a rerecording of a 1998 cut that was never released as a single.

“The Firefly’s Song” sounds like something Alan might have written himself, and Alison and Lee Ann Womack’s angelic harmonies only deepen the song’s earnestness.

“Kiss an Angel Good Mornin’”

From his 1999 album Under the Influence. Written by Ben Peters.

The first time I heard “Pop a Top,” it wasn’t Jim Ed Brown on lead — it was Alan Jackson. His album of traditional country covers includes this Charley Pride classic, which sits perfectly in Alan’s range.

I can add Alan Jackson to the list of lucky-I-got-to-see-‘em-live artists since, like Garth, I saw him at the Grand Ole Opry in the mid-‘90s. My family and I had balcony seats again, but Alan connected with everyone.

Alan will give his final concert at Nashville’s Nissan Stadium this June. He announced his retirement due to a rare genetic condition that affects his balance and ability to walk. While it’s a shame fans won’t get to see his live shows anymore, what a gift to go out in a sold-out stadium in Music City.

Do you have tickets?

We’ll close the book on this set of musical memories when we break down Travis Tritt’s career. I’ll be ready to share my Class of ’89 playlist with you when we do. Thanks for reading!

Garth Brooks 

Blame it all on my roots, I showed up in boots 

With the opening line of his hit single celebrating the value of having “Friends in Low Places,” Garth Brooks changed country music forever and cemented his place in its history. 

I was in fifth grade and had no idea what the lyrics meant. Still, I sang every word with as much twang as I could muster. Many of my friends — and countless folks across the country — were doing the same. 

Though I don’t know how to quantify it, I’m confident that Garth’s tremendous success opened the door for some terrific country artists — some of whom would never have gotten their shot otherwise. Record companies were willing to take more chances and bankroll more albums because Garth proved country music could be wildly profitable on a global scale. 

He consistently broke long-held records for album and ticket sales — even surpassing Elvis and The Beatles in some categories — and won dozens of awards by combining honky-tonk twang with rock ’n’ roll showmanship. 

Even during a four-year sabbatical to be more present for his daughters, Garth kept a firm grip on the hearts of his fans so that 37 years after his 1989 debut, he’s still selling out arenas and stadiums all over the world. Two things define his reign: his dramatic storytelling and the “it” factor. 

Drama king 

In Part I of this series, I briefly wrote about the similarities in both style and substance between Class of ‘89 artists Garth, Clint Black, Alan Jackson, and Travis Tritt. They’re neotraditionalists with a talent for what Dolly Parton has coined songtelling — that unison of songwriting and storytelling that makes country music special.  

Clint is to philosophy as Garth is to drama. 

From singles like “Papa Loved Mama” and “That Ol’ Wind” to album cuts like “New Way to Fly” and “The Night I Called the Old Man Out,” Garth has a flair for the dramatic. In his songs, he tells vivid stories of breakups and makeups, wishes denied and dreams fulfilled, life and death, and everything in between. 

As so many of his fellow ‘90s country stars learned, pairing those songs with cinematic music videos brought his stories to life in new ways and expanded his reach even further.  

In “The Thunder Rolls,” Garth transformed his appearance, hiding under a fake beard, wig, and glasses to play the cheating, abusive husband as Garth the singer performs in the pouring rain to narrate the tragic events. 

The video broke ground in country music, tackling head-on the taboo subject of domestic violence and paving the way for artists like Martina McBride to boldly address social issues in their songs and music videos. 

Later, Garth would give us “Standing Outside the Fire,” an emotional music video that follows a high schooler’s quest to compete on his school’s track team instead of in the Special Olympics. Because he has Down syndrome, his father fears that he’ll embarrass himself. Though the boy falls during the race, his dad, recognizing his son’s strength and persistence, encourages him to finish strong. In a shrewd move, Garth doesn’t appear in the video until two minutes into the song, deepening viewers’ investment in the boy’s story. 

In “The Dance,” written by Tony Arata, video footage of American icons — from civil rights leader Martin Luther King Jr. to Western film star John Wayne to World Champion bull rider Lane Frost — adds layers of new meaning to the song.  

Though his first album, 1989’s Garth Brooks, which included “The Dance” and three more Top 10 hits, was a bona fide success, his follow-up No Fences established his legacy. “Friends in Low Places” became his signature song and a No. 1 hit that, when performed live, shows off the indefinable characteristic that makes Garth a transcendent superstar. 

“It” factor 

The “it” factor is hard to define. It’s not just one quality but several that combine to make unforgettable magic. 

Garth’s “it” factor is most obvious in his concerts. His live shows, made more accessible by broadcast TV deals that beamed those experiences to the masses, were opposite of what most people expected from a country singer at the time. He smashed acoustic guitars, sprayed bottles of champagne, climbed the scaffolding on stage, and flew over the audience suspended by wires. 

I’ve only seen Garth live once, and it wasn’t his concert. When my parents, one of my brothers, and I got lucky and caught him at the Grand Ole Opry, it was a much more muted performance. Garth holds the Opry and its history in high regard, so there were no theatrics that Saturday night.  

Still, when he walked on stage, the floor shook. He sang three or four songs to an absolutely enraptured audience, connecting with fans like us in the balcony and the luckier ducks on the front row. That genuine connection and devotion to his fans is a big piece of his magic. Remember when he signed autographs and took pictures with fans for 23 hours straight at the 1996 Fan Fair in Nashville? 

A savvy businessman, Garth used exclusive deals with Walmart and later live Facebook episodes of “Inside Studio G” to build his brand. While I think he went too far with the “G-spot” on his website, I can appreciate that his branding goes beyond the lowercase “g” logo or the Friends in Low Places Bar & Honky-Tonk. Reciprocating his fans’ adoration, Garth created a community that’s still introducing new converts to country music. 

Whether you’re a longtime listener or one of the newbies, I hope you’ll check out my favorite songs from the ‘90s king. 

My Top 5 Favorite Garth Brooks Songs 

“Much Too Young (to Feel This Damn Old)” 

From his 1989 album Garth Brooks. Written by Garth Brooks and Randy Taylor. Peaked at No. 8 on the Billboard Hot Country Singles chart. 

I liked this song before it mattered to me. In my early 20s, I was really struggling. Driving through town one day, I heard this song on the radio and felt it in my very bones. You don’t have to be banged up from a grueling rodeo circuit to realize you’re much too young to feel this damn old. 

“More Than a Memory” 

From his 2007 album The Ultimate Hits. Written by Lee Brice, Kyle Jacobs and Billy Montana. No. 1 on the Billboard Hot Country Songs chart. 

What a well-written, gut-wrenching song that’s as Garth-esque as anything he’s written. The first time I heard it, I was convinced he had. Garth fully inhabits the song’s narrator and challenges himself vocally much like he does on his 1991 hit “Shameless.” 

“The Beaches of Cheyenne” 

From his 1995 album Fresh Horses. Written by Garth Brooks, Bryan Kennedy and Dan Roberts. No. 1 on the Billboard Hot Country Songs chart. 

This ghost story details the breakup of a couple after the rodeo cowboy goes back on his word to his beloved to withdraw from a bull-riding event. He’s injured and killed, and she’s consumed by grief. Her diary tells of their fight and her regrettable words to him before his death. But the rumor is she’s still alive. You can even see her footprints in the sand because every night she walks the beaches of Cheyenne. The storytelling on this one is chef’s-kiss perfect as is the fiddle intro.

“What She’s Doing Now” 

From his 1991 album Ropin’ the Wind. Written by Pat Alger and Garth Brooks. No. 1 on the Billboard Hot Country Songs chart. 

Back when Garth had his own channel on Sirius/XM, I always enjoyed hearing the behind-the-scenes stories he told about his songs. This one surprised me because he described the idea behind it as little more than a lark. “What would it be like to call an ex’s number?” The finished product is far more serious, and I love how the lyrics shift from him wondering what she’s doing now to wondering if she knows that he’s wondering what she’s doing now. Does she know that he isn’t over her? 

“One Night a Day” 

From his 1993 album In Pieces. Written by Gary Burr and Pete Wasner. Peaked at No. 7 on the Billboard Hot Country Songs chart. 

There are probably three or four songs I could put in this slot, but this is today’s Top 5. “One Night a Day” stands out because of its departure from Garth’s usual twang. It’s bluesy and features only piano, saxophone, bass guitar and drums. There are times when singers step outside of their comfort zones when you wish they hadn’t. That’s not the case here. 

Bonus Album Cuts 

“Mr. Blue” 

From his 1990 album No Fences. Written by Dewayne Blackwell. 

Garth managed to make this pop-jazz cover of a 1959 No. 1 hit by the Fleetwoods all his own, giving fans an early glimpse into his diverse music tastes. 

“Mr. Right” 

From his 1992 album The Chase. Written by Garth Brooks. 

Clever and upbeat. I’m Mr. Right forever or just until whenever/ Mr. Right or Mr. Right now 

“The Night Will Only Know” 

From his 1993 album In Pieces. Written by Garth Brooks, Stephanie Davis and Jenny Yates. 

Even juicier than “The Thunder Rolls” or “The Beaches of Cheyenne,” this album cut with risqué subject matter includes an affair, a murder and a cover-up. Find another country song that rhymes innuendos with steamy windows, and I’ll buy you a Coke. 

What’s your favorite Garth Brooks hit? Are you into his early stuff or do you play his more recent hits on repeat? Let me know in the comments and come back to Roots & Rhinestones for Part III of the Class of ‘89 series featuring the champion of the small-town Southern man, Mr. Alan Jackson.  

Clint Black

In 1989, a quartet of new artists ushered in an era of country music that built on the neo-traditional sounds of Randy Travis, Ricky Skaggs, Reba, and George Strait and led to an unprecedented boon for the genre. Their rising tide of success would lift countless boats in the sea of ‘90s country and earn them the collective nickname of the Class of ‘89. 

Clint Black, Garth Brooks, Alan Jackson, and Travis Tritt introduced themselves to the masses with Killin’ Time, Garth Brooks, Here In The Real World, and Country Club, respectively. Their sound and songwriting were steeped in tradition: Musically, they leaned heavily on fiddles and steel guitar, and lyrically, they honored the classic country themes of heartbreak and home, with plenty of drinking references thrown in for good measure. 

But their contemporary spin — from blending traditional instruments with electric guitars and keyboards to more narrative-driven songwriting styles — made country music sound new. And when Garth won over audiences with live shows influenced by rock legends like KISS, country music morphed into a bankable commodity few thought possible. 

Their songs are the soundtrack of my youth, and all these years later, I’m still singing along to their impressive catalog of hits. So, taking the group in alphabetical order, let’s dive into Clint Black — a modern-day poet and gifted musician obsessed with time. 

“State of Mind” 

When I first considered starting Roots & Rhinestones, lyrics from Clint Black’s “State of Mind” weighed heavy on my heart: 

Ain’t it funny how a melody can bring back a memory/ Take you to another place in time/ Completely change your state of mind 

I was 12 years old when the song came out, and I can still remember watching the music video: Clint walking down a desert highway, guitar case in hand. Later, the scene shifts to Clint and his band, dressed in Western ribbon ties and cowboy hats, playing under the stars to a small crowd of couples dancing in the dirt. 

I didn’t understand why the lyrics to this simple song hit me so hard at the time, but they stuck with me, as did my love for what can only be described as Clint Black’s poetry. Clint was fortunate to find a kindred spirit and songwriting partner in Hayden Nicholas, a fellow Texan who also plays lead guitar in Clint’s band. Together, they have written more than 60 songs, sending 15 of them to the top of the charts. 

In fact, their first three singles were No. 1 hits, and Black’s self-penned “Nobody’s Home” was his fourth consecutive No. 1. Not a bad way to start a career. 

I could quote Clint Black lyrics all day, but allow me to give you a just a sampling of favorites: 

When you find another friend who’ll light your candle up again/ You can burn one down for me (“Burn One Down”) 

I still comb my hair the same/ Still like the same cologne/ And I still drive that pick-up truck/ That the same old bank still owns (“Nobody’s Home”) 

It’s a little and a lot to ask/ An endless and a welcome task/ Love isn’t something that we have/ It’s something that we do (“Something That We Do”) 

No time to kill, but time to change the kind of hurry I’ve been in/ And quit this work and worry looking back at where I’ve been/ If you don’t look ahead, nobody will, there’s no time to kill (“No Time to Kill”) 

Early in his career, Clint impressed critics and fans with the emotional precision of his songwriting. In his debut single, “A Better Man,” Black reaches out to a former love to explain how their failed relationship had an unexpected positive result. It’s a sweet tribute to lost love that he followed with “Killin’ Time,” a song that continues to define his career. 

You were the first thing that I thought of/ When I thought I drank you off my mind/ When I get lost in the liquor/ You’re the only one I find/ And if I did the things I oughta/ You still would not be mine/ So I’ll keep a tight grip on the bottle/ Gettin’ loose and killin’ time 

Clint’s first three albums tell us a lot about the music he grew up listening to — Haggard, George Jones, and the Western swing music pioneered by Bob Wills and His Texas Playboys. Even his music videos showed his honky-tonk roots. Both “A Better Man” and “Killin’ Time” have the feel of watching TNN’s “Club Dance.” 

Though his songwriting was fresh, his music videos were mostly “live” performances wrapped in loose storytelling until he experimented with “When My Ship Comes In.” In a white dress shirt blowing in the wind and without his signature cowboy hat, Clint navigates a sailboat through the Rocky Mountains, faithful dog at his side, eventually arriving in a sunny, tropical destination. 

We’re willing to take that trip with Clint because, even though everyone knows you can’t “sail right out of Colorado,” we can relate to cabin fever and loneliness and that feeling that there’s something better waiting out there for us. 

His personality shines in the cameo-filled “Summer’s Comin’” starring Howie Mandell. Clad in a wetsuit and cowboy hat, Clint shows off his impressive electric guitar licks. “Blossom” star Joey Lawrence closes the video with his signature “Whoa” catchphrase in a brilliant piece of ‘90s pop culture adoration. 

But nothing defines Clint Black’s career like the theme of time. 

Killin’ it and spendin’ it 

Even as a teenager, I understood the importance of Clint’s reflections on time. From 1989’s Killin’ Time to 1993’s No Time to Kill, it was clear he had given a lot of thought to the seconds and minutes that measure our days.  

If I’m not mistaken, No Time to Kill was the first Clint Black album I owned, and I listened to it faithfully. I loved the vocal acrobatics of the title cut — which when done correctly as Clint does, and I never could — require breathing exercises to train the diaphragm. 

While I was more focused on my breathing back then, it didn’t take too many years for me to grasp the wisdom of Clint’s words and the poetry of his lyrics. 

After a four-year break from recording, Clint revisited the theme of time with 2004’s Spend My Time and accompanying title track. Reading those lyrics now, I get chills. “Spend My Time” is another philosophical reflection on life: 

I’ve many miles behind me, maybe not so much ahead/ It seems I made good time with the directions I misread 

Even without a No. 1 hit since 1999’s duet with his wife Lisa Hartman-Black, songs like “Spend My Time” prove his songwriting skills are as sharp as ever. As I’ve said before, charts aren’t the only — or even the most important — measure of success. Clint Black is still writing and recording music, touring and connecting with fans across the world. I was fortunate to see him at the Soybean Festival in Martin, Tennessee in 2017, and he filled my ‘90s country heart with joy. 

Clint also hosts a Circle TV series called “Talking In Circles,” inviting some of his friends in the entertainment industry to “talk shop” about music, movies and more. I’ve watched a few episodes, but one that’s especially relevant to Roots & Rhinestones is his sit-down with Travis Tritt, which you can watch here. 

To Travis, Clint says, “I think the whole industry exploded in ‘89. It wasn’t just us, but we were in that first wave.” That first wave boosted the careers of established stars and brought a host of like-minded new artists to Nashville. 

For that — and for all the melodies that bring back memories — Clint Black deserves to join his fellow 1989 “classmates” Garth and Alan in the Country Music Hall of Fame. And I can prove it with five of my favorite songs. 

My Top 5 Clint Black Songs 

1. “Nothin’ but the Taillights” 

From his 1997 album of the same name. Written by Clint Black and Steve Wariner. No. 1 on the Billboard Hot Country Songs chart. 

When it comes to songwriting and playing guitar, Clint Black and Steve Wariner are two titans of their industry. Their sizable talents in both departments are easily showcased on this up-tempo break-up song served with a side of sweet revenge. This is, hands down, my favorite Clint Black song. 

2. “Killin’ Time” 

From his 1989 album of the same name. Written by Clint Black and Hayden Nicholas. No. 1 on the Billboard Hot Country Songs chart. 

When the Country Music Association Awards celebrated its 50^th anniversary show, they brought out all the stops for the opening medley of hits. Generations of stars — Charley Pride and Roy Clark, Alabama and Dwight Yoakam — performed some of their biggest songs. When Clint took the stage to sing “Killin’ Time,” it was cool to see Reba, Carrie Underwood, and Alabama behind him on the stage singing along. 

3. “One Emotion” 

From his 1994 album of the same name. Written by Clint Black and Hayden Nicholas. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

He has better songs, but there’s something about this one that pulls me in every time. I wish I had the musical vocabulary to describe why “One Emotion” feels like peak ‘90s country to me.  

4. “When My Ship Comes In” 

From his 1992 album The Hard Way. Written by Clint Black and Hayden Nicholas. No. 1 on the Billboard Hot Country Songs chart. 

Clint’s headed to “Puerta No-One-Knows.” I didn’t know Puerta was door or gate in Spanish, but I understood the spirit of adventure when Clint declared he would “catch a ride on a warm trade wind” to that peaceful destination.  

5. “Put Yourself in My Shoes” 

From his 1990 album of the same name. Written by Clint Black, Hayden Nicholas, and Shake Russell. Peaked at No. 4 on the Billboard Hot Country Songs chart. 

From the bluesy harmonica intro to the clever lyrics to the Texas twang, this one is playful without being condescending. He goes into a higher register on the final chorus, which is something he rarely does, lending a touch more gravitas to his plea for another chance. What woman wouldn’t let Clint walk right back to her? 

Bonus Album Cut 

I typically give you three bonus album cuts, but doing so in this case would be disingenuous. His singles are my favorites, and holding that list to five was difficult. There is one album cut that readily comes to mind for Clint. It’s both a tribute to his heroes and peers and a great example of his craftsmanship as a songwriter. 

“Tuckered Out” 

From his 1993 album No Time to Kill. Written by Clint Black and Hayden Nicholas. 

Check it out live from the 1993 CMA Awards to see his country music references come to life on the big screen behind him.

What Clint Black melody brings back a memory for you? Share it in the comments. 

Up next is Garth Brooks, a bona fide superstar who took country music to new heights and can still sell out a stadium in mere minutes. 

‘Tis the season to take a break from the routine and celebrate the holidays. I’ll get back to my usual artist spotlight next time, but today I want to share some of my favorite Christmas songs recorded by (mostly) ‘90s country artists. 

I’ve established a couple of rules for the playlist. 

Rule No. 1 

I’m only including artists that were actively recording or performing in the 1990s. That lets me sneak in Brad Paisley and Montgomery Gentry, who debuted in ’99, though they didn’t release Christmas songs until the ’00s. 

Unfortunately, the rule eliminates recent country covers, including Carrie Underwood’s “Do You Hear What I Hear” and Brett Eldredge’s “I Heard the Bells on Christmas Day.” These are both worthy additions to other holiday playlists but don’t fit the bill for this one. 

Rule No. 2 

Since my focus is on country music, many legends of the season are missing. While I hope you’ll add my country favorites to your Christmas playlist, make sure to include the classics: Dean Martin, Nat King Cole, Bing Crosby, Rosemary Clooney, and Elvis. Lots of Elvis.  

Rule No. 3 

While my all-genre Christmas playlist on Amazon Music includes entire albums, for this list, I’ve limited myself to only one song per artist.

Not a rule, but a rant 

Is Die Hard a Christmas movie? Use that mentality to consider songs like “Let It Snow” or “Winter Wonderland.” They don’t specifically mention Christmas, but we accept them as seasonal songs. It would be weird to hear them playing at the grocery store in July. 

Dolly Parton’s “Hard Candy Christmas” and Merle Haggard’s “If We Make It Through December,” however, should be enjoyed year round. They aren’t Christmas songs, although Dolly’s certainly feels more Christmas-y. 

But it doesn’t matter how much I like the artist — Martina McBride, Trisha Yearwood, Brad Paisley — I cannot abide “My Favorite Things” being passed off as a Christmas song. It is not. Play it in April or September, but do not play it for Christmas. 

With that off my chest, we can dive into the list.

My Top 25 Country Christmas Songs

Alphabetized by artist’s first name

“Tennessee Christmas” — Alabama 

From their 1982 album Christmas. Written by Gary Chapman and Amy Grant. 

Before Amy Grant married Vince Gill and into the country music family, she and her first husband wrote “Tennessee Christmas,” a song that perfectly captures Christmas in the volunteer state. Including her recording on the list would violate Rule No. 2, so I chose the Bama boys’ version. Eight-year-old Crystal would give the nod to “Thistlehair the Christmas Bear,” but middle-age Crystal hopes for a “tender Tennessee Christmas.” (I will accept any arguments that “Christmas in Dixie,” written by band members Mark Herndon, Randy Owen, Jeff Cook, and Teddy Gentry, is the more suitable option for the group’s entry on this list.) 

“Holly Jolly Christmas” — Alan Jackson 

From his 1993 album Honky Tonk Christmas. Written by Johnny Marks. 

Alan put his honky-tonk spin on the season with a package of new and old favorites that included some compelling duet partners in Alison Krauss, Keith Whitley, and even Alvin and the Chipmunks. His smooth baritone wraps “Holly Jolly Christmas” up like a present under the tree. 

“364 Days to Go” — Brad Paisley 

From his 2006 album Brad Paisley Christmas. Written by Brad Paisley and Kevin Marcy. 

If you like electric guitar solos and Christmas music, Brad Paisley is your guy. (He recently released his second Christmas album, Snow Globe Town, with even more solos.) But in “364 Days to Go,” Brad’s knack for capturing life’s small details shines as he paints the soft glow of Christmas night through the eyes of a six‑year‑old — a mix of wonder and restless anticipation. 

“Rockin’ Around the Christmas Tree” — Brenda Lee 

Recorded in 1958 with a B-side of “Papa Noel.” Written by Johnny Marks. 

I may have cheated just a bit, but Brenda Lee was performing in the ‘90s. In fact, the 80-year-old rockabilly pioneer is still performing — and this hit is by far her biggest. She was only 13 years old when she recorded what would become a beloved Christmas favorite. I don’t remember the first time I heard it, but I wouldn’t be surprised if it was in the 1990 movie, “Home Alone,” which gave Brenda Lee a late career boost. Check out this video of Ms. Brenda describing the song she calls a “gift.”

“Milk and Cookies (‘Til Santa’s Gone)” — Clint Black 

From his 1995 album Looking for Christmas. Written by Clint Black, Hayden Nicholas, and Shake Russell. 

Clint and his cowriters put themselves inside the mind of the song’s 5-year-old narrator to channel those night-before-Christmas jitters: Close my eyes and concentrate/ I gotta sleep now it’s getting late/ All night long I lie awake/ ‘Til Santa’s gone I just can’t wait. Paired with a bright melody and Clint’s harmonica licks, this song is a ‘90s country classic. 

“Have Yourself a Merry Little Christmas” — Crystal Gayle 

From her 1986 album A Crystal Christmas. Written by Hugh Martin and Ralph Blane. 

I have a vivid memory of watching this music video on CMT at my grandparents’ house on a Christmas Eve night when I was little. With her long, black hair flowing, Crystal descends a staircase wearing a chic white sweater and dark slacks. She quickens the tempo to give the song a different feel than what you’ll hear from Judy Garland or Crystal’s fellow country singer Vince Gill. Hers is more hopeful than melancholy, and I’m for it. 

“With Bells On” — Dolly Parton & Kenny Rogers 

From their 1984 album Once Upon a Christmas. Written by Dolly Parton. 

You can’t listen to this one without tapping your foot and smiling along, but I should address why “Hard Candy Christmas,” written by Carol Hall, didn’t make the list. Dolly has said the song isn’t a Christmas song, but she included it on this album and has performed it for various Christmas specials. Unlike “My Favorite Things,” I like hearing it this time of year. It’s on my all-genre Christmas playlist in various forms — from Reba’s stripped-down acoustic cover to Trisha Yearwood backed by an orchestra. Just this week, I discovered Zach Top’s version on YouTube. Still, Dolly’s will always be the best. 

“Santa Claus is Back in Town” — Dwight Yoakam 

From his 1997 album Come on Christmas. Written by Jerry Leiber and Mike Stoller. 

Since I couldn’t include Elvis on this list (see Rule No. 2), I chose an artist who has the same self-assured swagger as the King. His rendition of one of Elvis’s Christmas classics is as feisty as the original. 

“A Baby Changes Everything” — Faith Hill 

From her 2008 album Joy to the World. Written by Craig Wiseman and Tim Nichols. 

I included this one on my list of Top 5 Faith Hill Singles because I love it that much. Her gospel roots blaze through this ballad about a young mother’s recognition that a baby changes everything for her. This baby — Jesus — also changes everything for the world.  

“Belleau Wood” — Garth Brooks 

From his 1997 album Sevens. Written by Garth Brooks and Joe Henry. 

A haunting song that gives me chills, Garth’s Belleau Wood isn’t included on any of his Christmas albums, yet it tells the story of the World War I Christmas truce of 1914. While the title references the Battle of Belleau Wood in France, the truce itself occurred when German and British soldiers exchanged greetings in no man’s land, sparking a widespread unofficial ceasefire. Like “If Tomorrow Never Comes” and “Unanswered Prayers,” Garth here reveals his gift for crafting songs of emotional gravity. 

(“It Must Have Been Ol’) Santa Claus” — Gary Allan 

From his 2021 EP Please Come Home for Christmas. Written by Harry Connick Jr. 

Christmas music is generally divided into two categories: sacred and secular. Within the secular division, you could also include a subgroup: sappy. There are plenty of sappy Christmas songs, and I like most of them, including Allan’s cover of the Eagles’ “Please Come Home for Christmas.” But I like his country-fied version of the New Orleans-flavored (“It Must Have Been Ol’) Santa Claus” even more. 

“Christmas Cookies” — George Strait 

From the compilation album A Country Christmas 1999. Written by Aaron Barker. 

Strait delivers this one flawlessly, talk-singing his way through the simple chorus and verses that hide a sweet love story in lyrics about cookies that look like Santa Claus/ Christmas trees, and bells, and stars. No one sings this one better than King George.

“There’s a New Kid in Town” — Kathy Mattea 

From her 1993 album Good News. Written by Don Cook, Curly Putman, and Keith Whitley. 

Although the wise men are routinely featured in retellings of Christ’s birth — from nativity scenes sold by retailers to children’s Christmas pageants — they aren’t largely included in music. But the magi narrate this story, which reminds us that the same Jesus that was mistaken “as just another baby” at his birth is still questioned as King and Messiah. I heard Kathy’s version before the Keith Whitley original, and it still stands out as one of the best. 

“The Nativity” — Lee Ann Womack 

From the 2001 compilation album Christmas Cookies. Written by Lee Ann Womack 

I think I’m right in saying Lee Ann wrote this one, but information online was spotty. Regardless, the song’s narrator reminisces about her mother’s nativity at Christmastime and the Easter service “at the Central Baptist Church.” In those memories, adult Lee Ann asks profound questions of herself and all modern-day Christians: Could I pursue the unknowing to accept Him in their home/ If I were there with Jesus would I help to right the wrong. 

“O Holy Night” — Martina McBride 

From her 1998 album White Christmas. Written by Adolphe Adam and John Sullivan Dwight. 

Few singers have the chops to meet the demands of this traditional carol, but Martina McBride’s control brings out both the reverence and grandeur of Christ’s birth. 

“Even Santa Claus Gets the Blues” — Marty Stuart 

From the 2003 compilation album A Very Special Acoustic Christmas. Written by Marty Stuart. 

Born in Philadelphia, Mississippi, and largely raised on the road touring with bluegrass legend Lester Flatt before joining Johnny Cash’s road band, Marty Stuart is a master of seamlessly blending country, rockabilly, and rhythm and blues. His recognition that even Santa gets the blues isn’t whiney but a reminder that sometimes we all get down, but we keep moving forward. 

“Merry Christmas from the Family” — Montgomery Gentry 

Released in 2000. Written by Robert Earl Keen. 

The country duo released their cover of Robert Earl Keen’s holiday ode to family dysfunction on the B-side of their single “All Night Long.” There probably aren’t a lot of country acts who could pull it off as well as Eddie and T-roy. Whether you call them rednecks or outlaws, you can picture them buying bean dip and Diet Rite at the Quickpak on Christmas.

“Christmas Time’s a Comin’” — Patty Loveless 

From her 2002 album Bluegrass & White Snow: A Mountain Christmas. Written by Tex Logan. 

Back when TNN churned out country music entertainment from Music City, Riders in the Sky hosted a Christmas special with guest star Reba McEntire. (I taped it and wore out that old VHS.) Their comedy-musical jam included “Christmas Time’s a Comin.’” Patty’s cover leans into bluegrass instrumentation, the perfect vehicle for her pure but raw delivery.

“Meet Me Under the Mistletoe” — Randy Travis 

From his 1989 album An Old Time Christmas. Written by Joe Collins, Mark Irwin, and Betsy Jackson. 

It was a toss-up between this one and “How Do I Wrap My Heart Up for Christmas” for Randy’s entry on the list. This one is more upbeat and a nice reminder for all you couples out there to make some time for each other during the busy holiday season. 

“A Christmas Letter” — Reba McEntire 

From her 1987 album Merry Christmas to You. Written by John Greenebaum, Paul Nelson, and Gene Nelson. 

As a kid, I could memorize lyrics quickly, but I rarely paid attention to the meaning of the songs I consumed. So even though I listened to Reba’s first Christmas album religiously, it was a while before I fully grasped that Santa Claus was the old man sitting alone at the antique desk, penning his own Christmas letter for peace on earth. Reba is at her My Kind of Country best on this album, and her voice and style fit the rustic imagery of this song. For extra credit, check out her version of “The Christmas Guest,” also on this album. 

“It Wasn’t His Child” — Sawyer Brown 

From their Wide Open album. Written by Skip Ewing. 

Like Garth’s Belleau Wood, this song was included on a non-Christmas album. Understandably, Joseph doesn’t get the same recognition as Mary, so a song from his perspective is compelling. Skip Ewing deserves a lot of credit for penning such thoughtful lyrics, and Sawyer Brown’s delivery is heartfelt.

“Beautiful Star of Bethlehem” — The Judds 

From their 1987 album Christmas Time with the Judds. Written by A.L. Philips. 

Wynonna provides a strong vocal foundation while Naomi adds unblemished harmonies to give this Christmas favorite a traditional country feel.

“Santa Looked a Lot Like Daddy” — Travis Tritt 

From his 1992 album A Travis Tritt Christmas: Loving Time of the Year. Written by Buck Owens and Don Rich. 

I’m not saying Travis does it better than Buck Owens because who can imitate Buck’s unique phrasing? But Travis certainly honors Buck with his worthy cover of Bakersville’s best. Brad Paisley’s version is also worth your time. 

“Take A Walk Through Bethlehem” — Trisha Yearwood 

From her 1994 album The Sweetest Gift. Written by Ashley Cleveland, John Barlow Jarvis, and Wally Wilson. 

When Trisha adds gospel flair to her traditional country voice, the results are darn-near perfect. Such is the case on this soul-stirring walk through Bethlehem. 

“Do You Hear What I Hear” — Vince Gill 

From his 1993 album Let There Be Peace on Earth. Written by Noel Regney and Gloria Shayne Baker. 

I don’t know if Vince introduced me to this song or if I simply learned the lyrics from his version, but it stands out in my memory. His pure tenor makes every Christmas song special, and this one is no exception. 

I know I missed some great songs — my mom may even withhold my Christmas present for leaving out her favorite, ‘Mary, Did You Know?’ But I’m confident these 25 will put you on the road to discovering even more country Christmas classics — from ‘90s artists and beyond — which is what Roots & Rhinestones is all about. 

I hope your heart is light this holiday season, but like Marty sings, “Even Santa Claus Gets the Blues.” Whether you’re grieving, far from family, facing illness, or overwhelmed by life’s challenges, you aren’t alone. Find education and resources on mental health at https://www.nami.org/support-education/. 

And if listening to Christmas music isn’t your jam, I’ll be back soon with the first of a series on the Class of ‘89, starting with a man I believe is destined for the Country Music Hall of Fame. Do you know who I have in mind? 

I grew up hearing my parents, alumni of the University of Tennessee at Martin, talk about the great concerts they attended on campus when they were students. UT Martin is much smaller than our state’s flagship campus, the University of Tennessee in Knoxville, but it pulled in some big acts back in the day. 

The school hosted fewer concerts when I was growing up in neighboring Gibson County, but the 1994 Soybean Festival brought Suzy Bogguss and Tim McGraw to Pacer Arena. I was in eighth grade, and my uncle took me to see the show.  

Times have changed since then. Skyhawks replaced Pacers as the UT Martin mascot, and the basketball teams now play in the Kathleen and Tom Elam Center. Tim McGraw hasn’t been an opening act in 30 years. And mercifully, I haven’t worn a suede vest over a t-shirt since that 1994 concert either. 

Suzy Bogguss’s clear, resonant voice remains as pure as ever. Influenced by singing cowboys Roy Rogers and Gene Autry and singer/songwriters Merle Haggard and Emmylou Harris, Suzy made a name for herself with her 1991 release Aces, her third studio album that produced three Top 10 hits and garnered her the 1992 Country Music Association Horizon Award (now known as New Artist of the Year). 

Three decades later, Suzy’s still recording and touring. Just a couple of weeks ago, her friend Kathy Mattea, on her own Grand Ole Opry induction night, invited Suzy to join the famed country music family shortly after taking the stage as a newly inducted member herself. Their fellow ‘90s stars Trisha Yearwood and Terri Clark were standing by with tears in their eyes as Suzy emotionally said yes. 

Suzy, Kathy, and Terri are bonded by more than their success in a golden decade. They’re also examples of what I like best about ‘90s country: there was room. Room for women and men who didn’t fit the mold of superstardom but carved out meaningful, lasting careers. Room for voices that were thoughtful and quietly powerful. Suzy wasn’t a stadium act, but she was a consistent presence on the radio and one of my favorite artists of the decade. 

In honor of the Opry giving Suzy Bogguss her due, let’s dissect the crystal-clear voice that has connected with fans for over 30 years. 

‘Like crystal water’ 

In 1994, Suzy Bogguss recorded Simpatico with guitar legend Chet Atkins. Known as Mister Guitar and the Country Gentleman, Chet Atkins was an architect of the Nashville sound, which mixed pop production values with traditional country instruments and songwriting. He produced records for some of country music’s finest, including Porter Wagoner, Dolly Parton, Eddy Arnold, Don Gibson, and Jim Reeves. 

When a guy known for having “a golden ear” wants to record an album with you, you’re doing something right. Before Simpatico, Chet Atkins wrote in the liner notes of Suzy’s debut album, “Her voice sparkles like crystal water.” 

Her voice is, indeed, as pure as a mountain stream. You hear it in the graduation standard “Letting Go” and the Western tentpole “Someday Soon” as clearly as the emotional “Aces” and underrated “You Wouldn’t Say That to a Stranger.” 

Suzy Bogguss has moved through the 2000s to the present with less chart success, but that hasn’t diminish how fans feel about her. Instead, we celebrate her experimentation with swing and jazz music on the Ray Benson-produced Swing and her cover of Chicago’s “If You Leave Me Now” on 2007’s Sweet Danger.  

Her radiant voice is at home on American Folk Songbook, which connects modern listeners to some of our country’s most important songs, and her 2014 album Lucky is a beautifully crafted love letter to Merle Haggard. Nobody sings Merle better than Merle, but her cover of “Silver Wings” is almost perfect. 

Suzy’s musicianship also shines through her recordings. I always appreciated that, like Emmylou and Kathy, Suzy clung to her guitar when other women set theirs aside. I can’t say whether she was pushing back against the norms of gender dynamics in country music or just more comfortable playing guitar while singing, but her talent and authenticity are undeniable. 

It was true way back in 1994 at Pacer Arena in Martin and again in 2008 when I saw her in an intimate performance at the Dixie Carter Performing Arts Center in Huntingdon. There’s no doubt in my mind that it’s still true today. 

Whether you’re a die-hard Suzy Bogguss fan, dusting off your memories of her, or totally unfamiliar, here are some songs that show off her warm, rich voice. 

My Top 5 Suzy Bogguss Songs 

1. “Just Like the Weather” 

From her 1993 album Something Up My Sleeve. Written by Suzy Bogguss and Doug Crider. Peaked at No. 5 on the Billboard Hot Country Songs chart. 

This is a sentimental favorite I’m putting at the top spot because it’s one of the few songs I can decently play on guitar. I love that Suzy Bogguss co-wrote and had a hit with this one with her husband Doug Crider. 

2. “Hey Cinderella” 

From her 1993 album Something Up My Sleeve. Written by Matraca Berg, Suzy Bogguss, and Gary Harrison. Peaked at No. 5 on the Billboard Hot Country Songs chart. 

After watching a friend get married and get older, the song’s narrator contemplates what the women in the song are missing. It’s a clever take on the old fairy tale, culminating a question for Cinderella: Does the shoe fit you now? Matraca Berg’s fingerprints are all over this gem. (Bonus: Reba McEntire officially inducted Suzy into the Opry on Jan. 16, 2026. A fan posted a video of Reba, Trisha Yearwood, Terri Clark, and Kathy Mattea helping Opry’s newest member out on “Hey Cinderella.” It’s guaranteed to put a smile on your face.)

3. “Drive South” 

From her 1992 album Voices in the Wind. Written by John Hiatt. Peaked at No. 2 on the Billboard Hot Country Songs chart. 

Early in her career, Suzy Bogguss showed a penchant for recording songs written by Americana singer/songwriters. It’s the first of three songs in my list that fit the bill. Ain’t gotta pack your nylons for this Hiatt-penned, carefree road trip. 

4. “Outbound Plane” 

From her 1991 album Aces. Written by Nanci Griffith and Tom Russell. Peaked at No. 9 on the Billboard Hot Country Songs chart. 

“Letting Go,” often performed at commencement ceremonies at the time, was my introduction to Suzy Bogguss. I ordered Aces from Columbia House largely for that song and was delighted to find “Outbound Plane” and “Someday Soon” on the same cassette. This is another up-tempo song with Americana vibes that sits right in Suzy’s sweet spot. 

5. “Someday Soon” 

From her 1991 album Aces. Written by Ian Tyson. Peaked at No. 12 on the Billboard Hot Country Songs chart. 

Lots of men and women have recorded this Western standard that leans heavily on Suzy’s singing cowboy influences. Just picture her strumming her guitar while riding a horse into the sunset and singing plaintively about the rodeo cowboy who has stolen her heart and her parents’ dreams for their daughter. 

Bonus Album Cuts 

“Forget About It” 

From her 1994 album Simpatico with Chet Atkins. Written by Robert Lee Castleman. 

I love Alison Krauss, and her 1999 version of this song is one of my favorites. I use the term “pure” to describe her voice as well as that of Suzy Bogguss, but there are different kinds of purity. While Alison wows and soothes with her angelic vocals, Suzy’s crystalline voice provides a slightly different but still powerful interpretation of the song. 

“If You Leave Me Now” 

From her 2007 album Sweet Danger. Written by Peter Cetera. 

True story: Suzy Bogguss introduced this song when I saw her live at The Dixie by telling the audience that she was surprised to hear an “American Idol” contestant namecheck her for covering the Chicago classic. I felt compelled to say aloud from my seat, “Yours is the best version.” She was kind enough to sign autographs and pose for pictures after the show, and I told her, “Yours really is the best version of ‘If You Leave Me Now.’” Her reply? “Ah, that was you.” My face flushed, and my mother had a good chuckle. Still, her voice is made for this song.

“Night Rider’s Lament” 

From her 1989 album Somewhere Between. Written by Michael Burton. 

Suzy yodels effortlessly on this poignant tribute to working cowboys and really any “outsiders” who defy convention and find freedom in solitude. I’m proud to say I’ve heard Suzy sing this one live twice, and each time gave me chills. 

What’s your favorite Suzy Bogguss song or album? Do you prefer her older stuff, or have you gotten into her newer material released on independent labels? Let me know in the comments as I chart where Roots & Rhinestones will take us next. I see a fork in the road: one path leads to the famed Class of 1989 — Garth Brooks, Clint Black, Alan Jackson, and Travis Tritt — and the other to the country-flavored tribute and cover albums I played on repeat in the ‘90s.