25 of the Best Country Songs of the 1990s (2024)

Country music from the 1990s got a bad rap in its day, including among dominant schools of music criticism. Despite, or because of, it being among the most popular genres in the world, 1990s country was regarded as a style without substance and not as country music.However, today, many 1990s country hits are regarded as classics–and with good reason. The music sounded bigger, louder, and more tuneful–and was far more commercially successful–than country had ever been.

Of course, its success stirred much debate in country music’s core communities, including among veteran musicians and music historians who argued that the country capital of Nashville had turned into “Nashvegas” with artificial “pop country”. In 2000, “traditional” country superstars George Strait and Alan Jackson even released a hit duet decrying the state of the genre, “Murder on Music Row“.

The sound many country fans associate with the decade is polished, high-energy, and friendly to pop audiences. Yet, in the context of country’s history, 1990s country fit into definitions of the genre as a commercial category, rather than a strictly musical, aesthetic, or lyrical one. While the sound of artists like Garth Brooks and Shania Twain furthered the pop and rock influences in country music, country music meant something different in 1999 than it did in 1990.

At the beginning of the decade, the new traditionalist moment in country was still strong, with artists like the Judds, Randy Travis, and George Strait all enjoying substantial commercial success with records that harkened back to earlier styles in country–often quieter, more acoustic guitar-based, with simple but effective storytelling. At the same time, newer artists like Garth Brooks were starting to reshape country music in exciting new directions, especially with greater rock influences in their music and stage shows.

By 1999, however, country had made unprecedented inroads onto pop radio, with artists like Shania Twain and Faith Hill enjoying Adult Contemporary hits with ballads that appealed to fans of both country and pop.

Each bookend is part of what made 1990s country great. This music was not a monolith; as with any era and genre, it was dynamic and evolving. Yet, in our age, many people remember the great hits of the era, especially after the new traditionalist moment had faded, as what 1990s country was about–and there’s a good reason for that.

Those hits–whether “Heads Carolina, Tails California“, “Don’t Take the Girl“, “Friends in Low Places,” “Boot Scootin’ Boogie“, “Fancy“, “He Thinks He’ll Keep Her“, “She’s in Love with the Boy“, “Here’s a Quarter (Call Someone Who Cares)“, or any number of others–were so indelible and indicative of the possibilities of where country music could go that they imprinted themselves on many people’s hearts, including mine.As a genre known for storytelling, country music reached a new peak for songwriting in the 1990s with exceptionally relevant and simple but sophisticated songs.

These days, 1990s country music is finally being taken more seriously. The astronomical sales figures of Brooks and Twain have meant that the Billboard charts have long registered the impact of such artists on popular culture. But it took decades for people outside of the mainstream of country music to realize how groundbreaking and brilliant 1990s country is–in addition to being fun, danceable, and worthy of appreciation.

In the last decade-plus, when many have lamented the presence of rapping and macho posturing in so-called bro-country, the music of the 1990s offers many a way back home–as, for some, older country styles did in the 1990s.

From hits nostalgic for 1990s country (Cole Swindell’s “She Had Me at Heads Carolina”) and songs about finding love to 1990s country hits (Kimberly Kelly’s “Summers Like That”) to songs lamenting the loss of pre-online technology (Hannah Dasher’s ingenious “1990’s Heartbreak”) to tribute albums (Americana group American Aquarium’s two volumes of 1990s covers, Slappers, Bangers & Certified Twangers), there seems to be a consensus in country music that 1990s country is especially worth celebrating in this age.

Of course, celebrating the past is nothing new in country music. 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 styles feels different. The love for 1990s country is much more present in country’s mainstream than older styles were in the 1990s.

While the middle-class-dominated alt-country/Americana movement reacted to the 1990s country boom by fetishizing an anti-commercial past, mainstream country today seems to value 1990s country for its commercialism–including its ties to sounds constructed as “pop” and “rock”.

Therefore, 1990s 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. True, the sound of the decade’s country was bigger and louder than country music had ever been, and it reached far larger audiences than the genre had ever attained.

However, technological changes in music and the marketplace magnified the international spotlight on country music. The advent of SoundScan technology in 1991, which resulted in a more accurate reflection of music sales, resulted in the genre’s unprecedented level of success on the mainstream pop charts.

In 1996, the Telecommunications Act resulted in the deregulation of communications markets, notably radio, where Clear Channel soon dominated national radio markets, including country radio. That meant more limited playlists concentrated on fewer commercially successful artists made it onto the airwaves. At the end of the decade, digital technology started making itself known in country music with Auto-Tune technology.

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, artists new to the mainstream, such as Twain, Trisha Yearwood, Mary Chapin Carpenter, Martina McBride, and Pam Tillis, were poised to maintain a lasting influence on country music. The mainstream moment didn’t last forever, but the women of the 1990s did make a considerable impact—still 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 Brooks, Alan Jackson, Clint Black, Travis Tritt, and Tim McGraw 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 and increasingly intricate stage productions.

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 more of a commercial tradition than one specific musical style. The 1990s 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 1990s country boom wasn’t as close to the country music tradition in terms of commercial success, class, or audience.

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 1990s, 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. I love the stories and the sounds of all eras of country music, but 1990s country has a special place in my heart.

For the list of my top 25 favorite country hits of the 1990s, I allowed one song per artist. Many fabulous artists, including some true giants of country music in the 1990s and beyond, did not make my top 25, but that doesn’t mean I don’t love those artists and their records. You can listen to each song, minus my pick for a certain giant whose music is only available on Amazon Music, on an ordered playlist (from #25-1) on Spotify or Apple Music.

25. Mark Chesnutt – “It’s a Little Too Late”

Mark Chesnutt tapped into older country music styles and nonetheless created some serious 1990s country foot-stompers, including “Bubba Shot the Jukebox” and this 1996 masterpiece. The lyrics lament a lost relationship, but the music–including a heavy backbeat, upbeat fiddle, Cajun-style accordion, and lean electric guitar–suggest sly celebration. Chesnutt’s other 1990s hits, including “Too Cold at Home“, “Brother Jukebox“, and “Let It Rain“, are also excellent.

24. Steve Wariner– “Holes in the Floor of Heaven”

Steve Wariner had been making hits for many years when he released this reassuring ballad, which won the Country Music Association (CMA) awards for Single of the Year and Song of the Year in 1998. Indeed, it’s a brilliant country song about the recurrence of rain as a symbol of the dead “watching over you and me”. Wariner’s vocal is passionate but restrained, and the strings are heavy but not overwhelming. “Holes in the Floor of Heaven” is one of its era’s more genuinely moving records.

23. Vince Gill – “Go Rest High on That Mountain”

Multi-instrumental virtuoso and singer-songwriter Vince Gill made perhaps his most significant contribution to country music with this song. With its spare, understated verses and soaring gospel chorus with Gill’s high tenor and harmonies from Patty Loveless and Ricky Skaggs, “Go Rest High on That Mountain”, an ode to Gill’s late brother is both mournful and celebratory–and one of my all-time favorite songs about grief. The song won Gill the CMA award for Song of the Year in 1995 and has deservedly endured as a classic in decades since.

22. The Judds – “Love Can Build a Bridge”

Wynonna and Naomi Judd began the decade as a standout group amidst the new traditionalist movement in country, with impeccably gorgeous close harmonies and years of commercial success. This 1990 song begins quietly with Wynonna’s unsentimental delivery, leading to a soaring gospel climax with a vision of the world as a beloved community. It’s hard for me to pick an “inspirational” country hit of the decade, but even more than “Go Rest High on That Mountain”, this is a very strong contender.

21. Alabama – “Angels Among Us”

Alabama had been country superstars since the late 1970s, but I doubt the group has ever put out a record as emotionally affecting as this one. I don’t care if you call 1993’s “Angels Among Us” cheesy–especially with the children’s choir, you might be right. But this song gives me a lump in my throat every single time I hear it. Randy Owen’s self-assured but occasionally trembling voice adds gravity to a potentially over-the-top ballad, making it one of its era’s more convincing “inspirational” records.

20. Mark Wills – “Don’t Laugh at Me”

Mark Wills’s 1998 hit “Don’t Laugh at Me” is a different kind of underdog anthem than what many associate with country music. This song cuts deep in and beyond class boundaries, with a different vulnerability than a breakup song. The lyrics and Wills’s performance work perfectly with the conventions of the genre. This song has always meant a lot to me as a symbolic voice for the bullied, downtrodden, and homeless. Soon performed by folk icons Peter, Paul and Mary as part of a movement against bullying (according to this documentary) and later rerecorded by Home Free with Wills, “Don’t Laugh at Me” has had one of the better afterlives of 1990s country hits.

19. Tim McGraw – “Where the Green Grass Grows”

From one of the most consistent hitmakers of the last three decades in any genre, I had trouble choosing one Tim McGraw hit for this list, especially compared to “Don’t Take the Girl“, “Everywhere“, “Please Remember Me“, “Just to See You Smile“, and “Something Like That“. But I chose this arena-sized anthem on returning to rural, pastoral living as my favorite 1990s McGraw hit. The heavy drums, emphatic guitar, and insistent fiddle stand out in the mix, and McGraw’s vocal seems fine-tuned to the setting. “Where the Green Grass Grows” lives on, including as a reference point in McGraw’s 2020 hit, “7500 OBO“.

18. Aaron Tippin – “You’ve Got to Stand for Something”

This anthem remains one of Aaron Tippin’s most remembered hits, and its assertive message justifies that status, no matter how equivocally the dominant culture in country music applies that message. Tippin’s confident vocal and the spare arrangement with mandolin, guitar, and fiddle help make this one of the most convincing 1990s country songs with overtly political implications.

17. Lonestar – “Amazed”

A few wedding songs in 1990s country are all-time classics, and “Amazed” is one of the best. Lonestar’s plaintive, yearning, and deeply sensual love song became country’s first #1 pop hit in over a decade in 1999.The keyboard-led production is polished without feeling slick, and Richie McDonald’s lead vocal is outstanding: credibly desperate without being over-the-top. His creaking on the final “you” makes me feel the lyrics even more.

16. Pam Tillis – “Spilled Perfume”

Today, Pam Tillis is one of the most underrated 1990s country stars. She is most remembered for the soaring “Maybe It Was Memphis”, but I’ve always preferred her more lyrically mature records, like “Deep Down“, “In Between Dances“, “All the Good Ones Are Gone“, “Land of the Living“, and this masterpiece. All show the increasing topical range of 1990s country songwriting, but Tillis’s sultry and knowledgeable vocal is especially convincing. Her phrasing sounds like she’s lived the “big difference between lonely and lonely for way too long”, and the result is stunning.

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25 of the Best Country Songs of the 1990s (2024)
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