My Top 10 Favorite '90s Country Music Hits

And why it matters now.

1990s country music is having a moment.

From current hits nostalgic for ‘90s country (Cole Swindell’s smash “She Had Me at Heads Carolina”) to songs about finding love to ‘90s country hits (Kimberly Kelly’s “Summers Like That”) and ones lamenting the loss of ‘90s technology (Hannah Dasher’s ingenious “1990’s Heartbreak”), there seems to be a consensus in the country music establishment that the ‘90s are especially worth celebrating in this age.

Of course, nostalgia is nothing new in country music. In fact, historian Bill C. Malone has long argued that nostalgia is the genre’s chief characteristic, and sociologist Geoff Mann sees that quality as the reason the music “sounds white,” both sonically and ideologically.

But something about this nostalgia for older country feels different. The love for ‘90s country is much more present in country’s mainstream than older styles were in the ‘90s. In fact, while the alt.country/Americana movement that reacted to the ‘90s mainstream country boom fetishized a particular vision of a supposedly anti-commercial past, mainstream country today seems to value ‘90s country for its ties to sounds constructed as “pop” and “rock”—in other words, the commercially appealing sounds of ‘90s country are a big part of what today’s country artists value in it.

Therefore, ‘90s country doesn’t so much have “retro” cachet as much as it feels like a critical link to current sounds and movements in mainstream country. Indeed, the 1990s were an unprecedented period in country music for several reasons. The sound of ‘90s country was bigger and louder than country music had ever been, and it reached far larger audiences than the genre’s artists had ever attained.

With technological changes for the music and the marketplace, the national and international spotlight on country music was magnified many times over. The advent of SoundScan technology in 1991, resulting in a more accurate reflection of music sales, resulted in an unprecedented level of presence on the mainstream pop charts.

In 1996, the Telecommunications Act resulted in the deregulation of communications markets, notably radio, where the company Clear Channel soon dominated national radio markets, including for country radio. That meant that more limited playlists concentrated on a smaller number of commercially successful artists made it onto the airwaves. At the end of the decade, digital technology was starting to make itself known in country music with Auto-Tune technology (see the controversy around Faith Hill’s “The Way You Love Me”).

Another shift in country music occurred with the rise of a greater number of female artists on the charts. In addition to chart veterans like Reba McEntire, newcomers to the mainstream like Shania Twain, Trisha Yearwood, Mary Chapin Carpenter, Martina McBride, Pam Tillis, and Wynonna (as a solo artist) were poised to maintain a lasting impact on country music. The mainstream moment for women didn’t last, but country’s women of the ‘90s did make a huge impact—and the impact is felt in the perseverance of female artists today, as shown in Marissa R. Moss’s 2022 book, Her Country.

The men held their own, however, with rising stars like Garth Brooks, Clint Black, Vince Gill, and Alan Jackson as well as established hitmakers like George Strait sometimes getting caught up in the trend of the so-called “Hat Acts” (as in cowboy hats), but nonetheless imprinting the music with lasting sounds and stories.

Despite my once stodgy “purism” about what is and isn’t country music, I recognize that, as scholars like Nadine Hubbs and Pamela Fox have argued, country music is a commercial tradition more than an acoustic, lyrical, or aesthetic one. The ‘90s were a particularly blood-boiling period for many purists who thought the music was getting far from its roots. However, just because it didn’t sound like older country music doesn’t mean it wasn’t country, and the truth is that the alt.country/Americana movement that grew in reaction to the ‘90s country boom wasn’t as close to the country music tradition in terms of commercial success, class, or audience.

As a recovering music snob, I once had a strong distaste for what music historian Colin Escott called “Stadium Country” in this era. But now, when I look back at the ‘90s, I don’t dwell on the alternative rock and hip hop canonized as the best music of the decade, as I once did. These days, I listen much more to country of that era—both mainstream and alt.country. I love the stories and the sounds of all eras of country music, but ‘90s country has a special place in my heart.

I decided to make a list of my top 40 favorite country hits of the ‘90s, one per artist—and my list quickly grew to overcapacity. Many favorites did not make my list—Ty Herndon’s “What Mattered Most” might have come closest to the top 40, but alas, it didn’t make it.

Below is my enumeration of my top ten picks, all of which were considered for #1. The complete list, minus my choice for Garth Brooks, is available in order from #40 to 1 on Apple Music and Spotify.

#10. “The Dance,” Garth Brooks

In any era of country music, this record would stand out. Its pensive melody and reflective lyrics—and more important, its haunting, moody arrangement and production—made Garth Brooks’s “The Dance” a classic that doesn’t sound, to this day, like anything else on the radio. Brooks’s passionate, sensitive, and measured delivery make 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 gently dominating throughout. Put simply, “The Dance” is a deserved classic.

#9. “Strawberry Wine,” Deana Carter

As I wrote earlier, country music is known for nostalgia, but this record put a whole new twist on the perennial theme of lost love.  Thematically, the subject is groundbreaking and steamy, but the waltz time beat, the steady acoustic guitar, lonesome fiddle, and ever-present steel guitar make this record feel as well-worn and comfortable as an old pair of blue jeans. Deana Carter’s vocal drips with palpable sensuality, longing, and regret, and what a great song and record can do is make the listener project their own desires onto a story like this. Of all the records that made my top ten, this may hold up the best as a record—that is, a produced recording, rather than just music and words on paper. This is a masterpiece.

#8. “Cowboy Take Me Away,” The Chicks

Before their career got trashed, the former Dixie Chicks made some of the greatest 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’s sensual and explosive delivery, this might be my favorite Chicks hit. And it lives on, including in covers by contemporary country artists Carly Pearce and Cameron Hawthorn.

#7. “How Can I Help You Say Goodbye,” Patty Loveless

What scholar Nadine Hubbs calls the Three-Verse Life Cycle song reached new heights with one of the greatest singers of the last four decades. “How Can I Help You Say Goodbye’s” stately melody and restrained delivery work well with Patty Loveless’s heart-tugging performance of the story of a mother-daughter relationship from the daughter’s youth to the mother’s death. Loveless is one of the most convincing and skilled singers around—in any genre, but especially in a genre known for outstanding storytelling, Loveless’s performance here is a knockout. “How Can I Help You Say Goodbye” might be her greatest tearjerker—even more than “You Don’t Even Know Who I Am,” also considered for this list.

#6. “The Hard Way,” Mary Chapin Carpenter

Mary Chapin Carpenter was a Brown University graduate from New Jersey who wrote incredible country songs in the ‘90s, and this wasn’t even among her biggest hits. But I chose “The Hard Way” for this list because of its drive and for its function as an anthem for women of country in the ‘90s (see this video if you don’t believe me). 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 both country and popular music in general, and “The Hard Way” is one of her finest moments.

#5. “He Didn’t Have to Be,” Brad Paisley

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 ‘90s country. While I wouldn’t rank this as the greatest country hit record of the decade, I would certainly nominate it for the greatest song. 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—I had read from the abovementioned Nadine Hubbs that it was a “potent tearjerker,” and 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.” In fact, perhaps no song from the ‘90s—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.

#4. “Like the Rain,” Clint Black

No artist combined swagger with vulnerability in ‘90s 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 record’s edginess, and the swaggering lead guitar line and reverb-heavy drums on the chorus make this one of the quintessential ‘90s country hits for me. And then there's Black’s voice, with its remarkable range and flourishes of tenderness and muscle. I love this record so much partly because of what it's done for me.

#3. “Fancy,” Reba McEntire

If there's one moment of electric force in all of ‘90s country, it’s when Reba McEntire belts out, “You know, I might've been born just plain white trash, but Fancy was my name!” This cover of a lesser known 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. “Independence Day,” Martina McBride

The chill(ing) factor continues to rise with this record. Initially a #12 Billboard country hit, it has since become a classic country record, far outlasting most, if not all, its chart competition at the time. The stakes quickly increase in this song, and by the time the chorus comes in, Martina 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.

#1. “When You Say Nothing at All,” Alison Krauss & Union Station

And so we get to #1. 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 combined tight bluegrass harmonies, contemplative balladry, and a ‘90s drum sound to make what to my ears is the most perfect country record of the decade. 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.