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.

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