15. Travis Tritt – “I’m Gonna Be Somebody”
Country music has many story songs that show how a theme develops over a lifetime, and Travis Tritt’s “I’m Gonna Be Somebody” is one of my favorites. Tritt is one of the best rockers and balladeers of his generation of country stars, and he made several records that I could’ve put on this list. Whether or not this record is as memorable as “Here’s a Quarter (Call Someone Who Cares)“, “T-R-O-U-B-L-E“, “Anymore“, or “Drift Off to Dream” is up for debate, but this record updates the classic country theme of “what goes around comes around” with the tale of a young man determined to become a star. Tritt has one of the most appealing voices in 1990s country, and his vocal on this song reflects the determination and grit of his subject.
14. George Strait – “Blue Clear Sky”
As much as “King of Country” George Strait is known for keeping older styles of country music alive, he adapted exceptionally well to the 1990s scene with more contemporary-sounding tracks like “Carried Away“, “I Cross My Heart“, and this rocker from 1996. Combining heavy drums and a classic pedal steel guitar, “Blue Clear Sky” bridged divergent ideas of country’s multifaceted traditions with an optimistic lyric and bright-sounding production.
13. Shania Twain – “You’re Still the One”
In the late 1990s, Shania Twain was the biggest star in country, with the biggest-selling album in country history. This sincerely optimistic love song with a languid, sensual vocal was a big reason why. Despite the later breakup of Twain and producer Mutt Lange, who sings backup on this record, this gorgeous track endures as one of the defining love songs of its era.
12. Jo Dee Messina – “Heads Carolina, Tails California”
Jo Dee Messina burst onto the country charts in the mid-1990s with this instant classic, one of the greatest escape-themed records ever made. Messina sounds fiercely determined and buoyant, with a defiant lead guitar line and cascading steel guitar–and a fantasy headed in the opposite direction of Tim McGraw’s “Where the Green Grass Grows”. The song lives on in the hearts of many, and not just because of Cole Swindell’s 2022 smash hit “She Had Me at Heads Carolina“.
11. Mary Chapin Carpenter – “The Hard Way”
Mary Chapin Carpenter is my favorite 1990s country artist. A Brown University graduate from New Jersey who wrote classic country songs like “He Thinks He’ll Keep Her“, “I Feel Lucky“, “Stones in the Road“, and “Down at the Twist and Shout“, Carpenter filled albums with observant, moving, and witty gems. But I chose “The Hard Way” for this list because of its drive and function as an anthem for women of country in the 1990s (see this clip for proof). Boldly announcing, “Actions speak louder”, including with its guitar intro, “The Hard Way”, among other masterpieces, cements her reputation—to me, at least—as one of the greatest singer-songwriters of her generation, regardless of genre. She brought a different kind of songwriting sensibility to country and popular music in general, and “The Hard Way” is one of her finest moments.
10. The Chicks – “Cowboy Take Me Away”
Before their career got trashed, the former Dixie Chicks made some of the best country records ever and achieved several remarkable feats, not the least of which was being seen as the best act in country by both mainstream radio programmers and country purists (see Bill C. Malone and Tracey E. W. Laird’s writing on them in Country Music USA). They also combined a distinctive, spunky personality with seriously skilled musicianship, and the bold declaration of “Cowboy Take Me Away” soared above country music of the time. With wistful steel guitar, tight harmonies, and Natalie Maines’ explosive delivery, this is my favorite 1990s Chicks hit. And it lives on, including in covers by contemporary country artists Carly Pearce and Cameron Hawthorn.
9. LeAnn Rimes – “How Do I Live”
As much as I love Trisha Yearwood’s records like “Walkaway Joe” and “She’s in Love with the Boy“, when she and LeAnn Rimes both released versions of “How Do I Live” in 1997, Rimes outdid Yearwood in more ways than one. Despite the song’s sentimental lyric, Rimes’s vocal–at fourteen years old, no less–is more mature, measured, and moving. Rimes’s powerhouse version became one of the biggest pop hits of the 1990s, and deservedly so.
8. Garth Brooks – “The Dance”
In any era of country music, this song would stand out. Its slowly unfolding melody and reflective lyrics—and, at least as important, its haunting, moody arrangement and production—made Garth Brooks’s “The Dance” a track that doesn’t sound, to this day, like anything else on the radio. Brooks’ passionate but sensitive and restrained delivery makes for one hell of a performance. It’s a record heavy on a different kind of atmosphere than a typical honky tonk stomper, with eerie strings, steel guitar whining low, and a keyboard that gently dominates throughout. “The Dance” is a deserved classic.
7. Patty Loveless – “You Don’t Even Know Who I Am”
With no disrespect to Trisha Yearwood, Wynonna, Reba McEntire, Vince Gill, or anyone else, Patty Loveless is my favorite country singer of the 1990s. Loveless, influenced by George Jones, skillfully manipulates her timing and timbre to wring emotions out of songs masterfully, and her performance on this song gives me greater chills and a bigger lump in my throat than most songs of its era. Its detail-oriented lyrics are tough enough to swallow in hearing about a couple’s breakup, but Loveless is a masterful country singer beyond most, and her 2023 induction into the Country Music Hall of Fame was well deserved.
6. Clint Black – “Like the Rain”
No artist combined swagger with vulnerability in 1990s country like Clint Black. That combination of qualities made Black more believable than many country acts of the time, and this is the thundering love song—in more ways than one—of the decade. The ominous melody establishes the song’s edginess, and the swaggering, lean lead guitar line and reverb-heavy drums on the chorus make this one of the quintessential 1990s country hits for me. And then there’s Black’s voice, with its remarkable range and flourishes of tenderness and muscle. This is my favorite Clint Black hit, among several strong contenders, and its unexpected meaning in my life makes it resonate still more.
5. Deana Carter – “Strawberry Wine”
Country music is known for nostalgia, but this record put a new twist on the perennial theme of lost love. Thematically, the subject is groundbreaking and steamy, but the waltz time beat, steady acoustic guitar, measured fiddle, and ever-present steel guitar make this record feel well-worn and comforting. Deana Carter’s vocal drips with palpable sensuality, longing, and regret. Of all the records that made my list, “Strawberry Wine” may hold up the best as a produced recording, rather than just music and words on paper, from a contemporary perspective. This is a masterpiece.
4. Martina McBride – “Independence Day”
Initially a #12 Billboard country chart hit, Martina McBride’s landmark “Independence Day” has since become a classic country song, far outlasting most, if not all, its competition at the time. The stakes quickly increase in this song, and by the time the chorus comes in, McBride has already changed the idea of appropriate subjects in country. Singing from the perspective of a daughter who lived after her parents’ murder-suicide following domestic violence, the song hits hard on any number of levels, and the guitars create tension alongside McBride’s powerhouse vocal. When McBride sings, “Talk about your revolution, it’s Independence Day,” I still get chills listening to it.
3. Reba McEntire – “Fancy”
There are many moments of electric force in 1990s country, but if one tops them all, it’s when Reba McEntire belts out, “You know, I might’ve been born just plain white trash, but Fancy was my name!” McEntire’s version of a Bobbie Gentry story song is a stunner, with a bigger sound and McEntire strutting her way through the story of an impoverished mother turning out her daughter for sex work. This cover was so emblematic that it became Reba McEntire’s signature song in her long and distinguished career of hits.
2. Brad Paisley – “He Didn’t Have to Be”
Coming at the end of the decade, hitting #1 on the country charts in December 1999, this record often gets forgotten among Brad Paisley’s many hits, as well as in the general narrative about 1990s country. This is my choice for the best-written country song of the 1990s, a story in lyrics and melody that seared itself into my consciousness. This simple but powerful tale about the relationship between Paisley and his adopted father caught me off guard so much when I first heard it that by the end of the first chorus, I was sobbing; I have said that this song “slaughtered me alive and served me up for breakfast”. Perhaps no song from the 1990s—none by Nirvana, 2Pac, Jeff Buckley, Tori Amos, Patty Loveless, or Vince Gill—so immediately impacted me emotionally. Paisley’s understated, matter-of-fact delivery undermines a potentially sentimental record and makes it more compelling. This doesn’t usually make lists of great ‘90s country hits, but it should.
1. Alison Krauss & Union Station – “When You Say Nothing at All”
This is my favorite performance of a love song in the history of country music. Alison Krauss has my favorite voice as a sound in the history of country music. And Keith Whitley was one of the great singers in country’s history, but Krauss outdid him on a song he made famous. This record combines tight bluegrass harmonies, contemplative balladry, and a 1990s drum sound to make one of the most perfect country records ever. And Krauss’s quiet, pure sound works wonders here: she says so much, saying “nothing at all” with an airy, wispy tone that’s pared down to the barest essentials. To me, this is the country vocal of the decade: a Hall of Fame-level performance for any Hall of Fame.
NOTE: Part of this article was previously published, though it has been significantly revised and expanded.