The 90s were a wild time for country music, with artists pursuing a variety of pathways to stardom. You had the pop sensations like Garth Brooks, Faith Hill, and Shania Twain crossing over to huge audiences. (Especially when Soundscan began reporting data in the early part of the decade.) You had courageous women like Martina McBride and Lorrie Morgan exploring issues that had barely been spoken about previously. There was a wing of independent artists pushing and pulling the genre in exciting new directions like Bonnie Prince Billy and Uncle Tupelo. And, of course, you had the traditionalists. Folks that simply perfected the form: George Strait, Alan Jackson, and Toby Keith among them. In short, the decade was fascinating, fun, and full of great music. Here are just a few of the classic country songs that you should add to your 90s playlist. (An important note: We only included one song per artist to get in as many different songs as possible.)
40: Tracy Byrd – Watermelon Crawl
Now here’s an unlikely theme for a song. A man arrives in a small town in Georgia, just as the local watermelon festival is kicking off. The locals enjoy a wine from their harvest that comes with a warning from the mayor: “Help yourself to some, but obey the law/ If you drink, don’t drive/ Do the watermelon crawl.”
39: Diamond Rio – Meet In the Middle
Formed in Nashville in 1982, it was almost a decade before Diamond Rio made their debut record, “Meet In the Middle.” Hitting the top spot on the Billboard Country chart with a Grammy-nominated debut gave them a lot to live up to, but over three decades later, they’re still going strong.
38: Daryle Singletary – Too Much Fun
A good-time romp with a catchy melody that celebrates a wild night on the town, “Too Much Fun” begins with a blue light flashing and gets wilder from there. Hailing from Cairo, Georgia, Singletary had moved to Nashville in search of stardom in 1990. With this 1995 smash hit, he found it.
37: Pam Tillis – Maybe It Was Memphis
“If I ever did anything right in my career,” Tillis would later comment, “it’s the fact that I didn’t give up on that song.” An unreleased cut from a 1980s recording session, but when she made a second pass at it for her 1991 Put Yourself In My Place LP, a star was born.
36: Joe Diffie – Pickup Man
Joe Diffie’s Christmas 1994 hit is a love song to that most country of vehicles: the pickup truck. “You can set my truck on fire and roll it down a hill/And I still wouldn’t trade it for a Coupe de Ville” he sings, while reveling in the double meaning of using his truck to pick up women.
35: Rhett Atkins – That Ain’t My Truck
When Rhett Atkins sees another man’s truck parked outside his girl’s house, he knows his whole world is over. “That Ain’t My Truck” was Atkins’ first chart-topper, and remains his signature song today, despite a decades-long career as both singer and songwriter. He was inducted into the Nashville Songwriters Hall of Fame class of 2021.
34: Lorrie Morgan – What Part of No (Don’t You Understand)
In 1992, Lorrie Morgan’s gutsy single “What Part of No (Don’t You Understand)” attracted praise in feminist circles for bringing into the open how it feels to be a woman out for an evening confronted by a man who won’t stop his advances, no matter how many times he’s rebuffed.
33: Kenny Chesney – You Had Me From Hello
Inspired by a line from the Tom Cruise and Renée Zellwegger movie Jerry Maguire, Kenny Chesney’s 1999 single “You Had Me From Hello” is a country ballad that typifies Chesney’s crossover appeal, which has seen him sell some 30 million albums.
32: Mary Chapin Carpenter – Passionate Kisses
Although written by Lucinda Williams in 1988, “Passionate Kisses” didn’t become a hit until five years later when Carpenter recorded it for her Come On Come On album. Both artists took home gongs for the recording at that year’s Grammy’s, however – Carpenter for Best Country Vocal Performance, and Williams for Best Country Song.
31: Collin Raye – Love Me
Collin Raye was born to be a singer. His mother, Lois Wray, was a musician who had opened for Elvis Presley. Later, Collin and brother Scott would join their mother on stage, before forming a band of their own. But it wasn’t until he became a solo artist that he finally hit the big time, with “Love Me.”
30: Lonestar – Amazed
This country power ballad gives a lyrical nod to Paul McCartney’s classic “Maybe I’m Amazed,” and has been covered by artists from Boyz II Men to Bonnie Tyler. But it was the 1999 Lonestar original that catapulted the Nashville group into the big time.
29: Trisha Yearwood – Walkaway Joe
The second single from Trisha Yearwood’s 1992 Hearts in Armor album, “Walkaway Joe” benefits from harmonies by Don Henley. Having been introduced to The Eagles singer backstage, Trisha Yearwood made what she described as an uncharacteristically bold approach: “He said he liked my music. I’m like, ‘Cool. Would you like to come sing on my record?’ And he did.”
28: Johnny Cash – Delia’s Gone
“Delia’s Gone’ is the Devil’s deed of daring,” Johnny Cash told Mojo magazine. “We were talking about ‘Folsom Prison Blues’ – and ‘I shot a man in Reno just to watch him die’ – and I said, ‘I want another song like that’.” The American Recordings LP the song appears on rejuvenated Cash’s career, winning awards and accolades around the world.
27: Steve Earle – Tecumseh Valley
Steve Earle’s 1995 Train Is Coming album, his first record following rehab for drug addiction, included powerful self-penned numbers as “Goodbye,” as well as covers of songs by The Beatles (“I’m Looking Through You”) and the Melodians (“Rivers of Babylon”). But nothing touched this stunning interpretation of Townes Van Zandt’s 1968 “Tecumseh Valley.”
26: Waylon Jennings – Wrong
By the 1980s, the outlaw-country star’s health was showing signs of suffering from decades of hard living. But despite ailing health, the country music legend still had hit songs left in his locker for the 90s. Taken from 1990’s The Eagle album, “Wrong” was an amusing number about a relationship that had turned sour, and would be his final country top 10 hit.
25: Rodney Crowell – Please Remember Me
Perhaps better known by Tim McGraw’s 1999 cover version, Crowell’s original of “Please Remember Me” is a heartbreaking recording. When asked to explain how a cover of such a personal song could be so successful, Crowell replied, “I would venture to say that Tim McGraw probably had lived it, in some way.”
24: Uncle Tupelo – No Depression
Before the Coen brothers’ 2000 movie O Brother ,Where Art Thou? prompted a country roots revival, Uncle Tupelo achieved cult status with heartfelt songs that recalled the style of Hank Williams, the Carter Family, and Jimmie Rodgers. After Uncle Tupelo split, singer Jeff Tweedy would achieve great success fronting alt. country legends Wilco.
23: Alison Krauss and Union Station – When You Say Nothing At All
Alison Krauss and Union Station may have been best-known for bringing bluegrass back into fashion in the early 1990s, but it was their cover of the Keith Whitley ballad that gave Krauss her chart breakthrough – and won her the 1995 CMA award for single of the year.
22: Bonnie Prince Billy – I See A Darkness
Since he first emerged under the name Palace Brothers in 1993, Will Oldham, AKA Bonnie Prince Billy, has been pushing country’s boundaries. The title track to his 1999 album I See A Darkness was later covered by Johnny Cash, while the LP was ranked at number 9 on Pitchfork’s list of best albums of the 1990s.
21: Trace Adkins – Every Light In The House Is On
Lonesomeness and heartache have long been familiar themes in country music, and “Every Light In the House Is On” has shades of George Jones’ “He Stopped Loving Her Today” – a classic song of a man who never gives up hope that his true love will return to him some day.
20: Brad Paisley – He Didn’t Have To Be
Brad Paisley has described his first no. 1 song as the most life-changing three minutes of his life. “I was really lucky,” he said. “It wasn’t like we knew what we were doing. I just happened [to write] that with my best friend from the bottom of my heart about his situation.” It’s a must-have for any 90s country music playlist.
19: Billy Ray Cyrus – Achy Breaky Heart
No 90s country songs list would be complete without the international smash hit that first sent the Cyrus name skyrocketing. Love it or hate it, the single popularized line dancing everywhere from Australia to the UK, and remains a karaoke favorite all over the world.
18: Toby Keith – Should’ve Been a Cowboy
Hailing from Oklahoma, Toby Keith debuted with a single that idealizes the Old West, with its roll call of figures such as Jesse James and the Texas Rangers, while namechecking those original singing cowboys, Gene Autry and Roy Rogers. As well as topping Billboard’s Hot Country Songs chart and becoming a mainstay on country radio, it also hit the Hot 100.
17: Vince Gill – Go Rest High on That Mountain
In a touching moment during his first concert as 2009’s artist-in-residence at the Country Music Hall of Fame, Gill explained how he wrote the song after his brother Bob’s death. “All I wanted to do was grieve for him and celebrate his life. That’s how I always process grief – sit down with a guitar and make something up.”
16: Emmylou Harris – Wrecking Ball
The title track from Harris’ acclaimed 1995 album features its composer, Neil Young, on backing vocals. The album was something of a departure of style for the Country Music Hall of Fame singer, but the experimental nature proved a huge success, opening her catalogue up to a whole new audience.
15: Lucinda Williams – Drunken Angel
“Drunken Angel” may have been written about the shooting of country singer Blaze Foley, but Lucinda Williams found it grew into something more universal: “The song has become something now that could be about Townes [Van Zandt] or Gram Parsons or Kurt Cobain or any artist who’s died too young and given up the ghost.”
14: Tim McGraw – I Like It, I Love It
This is one of the great country songs of the 90s, and was recorded at the legendary FAME studios in Muscle Shoals, Alabama – in the footsteps of such luminaries as the Rolling Stones, Aretha Franklin, and Otis Redding. McGraw is used to sitting among such company – with some 80 million records sold to date, he is one of the biggest-selling artists in music history.
13: Travis Tritt – Here’s a Quarter (Call Someone Who Cares)
“I was at home one day,” remembered Travis Tritt. “My wife had moved out in the middle of the day, while I was at work, and I came home to basically an empty house.” He was then served divorce papers, at which point his wife called to say maybe she’d been hasty. “And that’s when the lyrics came to me…”
12: Martina McBride – Independence Day
When “Independence Day” was released, in early 1994, it helped bring the conversation about domestic violence against women into the open. The song’s powerful ending was deliberately ambiguous in the song. However, songwriter Gretchen Peters admitted that in her mind, the woman dies in the fire at the end of the song.
11: Dwight Yoakam – Fast as You
Among the many 90s country fans is Kelly Clarkson, who covered “Fast As You” on her talk show. “Here’s the thing: I just love country music,” she said, before listing Dwight Yoakam among her favorite artists. She’s not alone – Yoakam is one of the biggest artists in country music history.
10: Deana Carter – Strawberry Wine
Deana Carter’s debut single, “Strawberry Wine,” is a coming-of-age song, where the protagonist is “Caught somewhere between a woman and a child.” The Country Music Association Awards Song of the Year in 1997, it romanticizes teenage nights sipping illicit (and sickly sweet) wine, while meeting boys, and losing more than just innocence.
09: LeAnn Rimes – How Do I Live
One of the best 90s country music songs, but also one of the best pop songs as well. Despite peaking at number two on the Hot 100, “How Do I Live” spent so long on the chart that it sits at number five on Billboard’s “all-time top songs.” It was the first of many tunes Rimes recorded by songwriter Diane Warren, whose other credits include Cher’s “If I Could Turn Back Time” and “Un-break My Heart” by Toni Braxton.
08: Alan Jackson – Chattahoochee
The 1994 Country Music Association Song of the Year is ostensibly about a childhood alongside Georgia’s Chattahoochee River. But Jackson found the theme was universal: “The regular working people, professional people, just trying to do the same things, make a living, raise a family, enjoy life. I learned that there’s a Chattahoochee everywhere.”
07: Faith Hill – This Kiss
It’s hard to believe any commercial tune would have the lyric “centrifugal motion,” but this is the song that broke Faith Hill outside of North America with a more pop style. The crossover and international success of “This Kiss” – not to mention two Grammy Awards nominations – justified the move, and the follow-up album, Faith, would sell some six million copies in the US alone.
06: George Strait – Blue Clear Sky
The 1996 smash hit from “The King of Country” owes its inception to a line from Forrest Gump – songwriter Bob DiPiero was struck by the poetry of Gump’s muddling of the phrase “clear blue sky.” Not surprisingly, it hit number one on the Hot Country Songs chart – one of 60 chart-toppers for George Strait, and more than any other artist in any genre.
05: Dixie Chicks – Wide Open Spaces
Back when The Chicks were still known as Dixie Chicks, their 1998 Wide Open Spaces album blew the doors to success wide open for the all-female country band. The title track is a celebration of the need for a young woman to make her own way in the world – and topped the country charts for four weeks.
04: Garth Brooks – The Dance
It’s impossible to have a best 90s country songs list without Garth Brooks. But which song to pick? “Friends in Low Places” could have just as easily made the cut. But we’re partial to “The Dance.” Three years before signing with Capitol Records, Brooks met songwriter Tony Arata, who played him the song. “Garth loved it the first time he heard it, and he said he wanted to record if he ever got a deal.” The day after signing, Brooks called Arata to say he was ready to make good on that promise. It became the title track of his debut album.
03: Brooks & Dunn – Boot Scootin’ Boogie
The single credited with reviving America’s love of line dancing was originally given away to Asleep at the Wheel, in 1990, before Brooks & Dunn’s own version appeared as the b-side to their 1991 “My Next Broken Heart” single. It was finally promoted to the a-side in 1992, and the rest is cowboy history.
02: Reba McEntire – Fancy
Country music fans would be hard-pressed to pick the best Reba McEntire song from the 90s. Is it “Is There Life Out There” or “The Heart Won’t Lie”? We opted for “Fancy,” which was originally written and recorded by Bobby Gentry in 1969. It’s a rags-to-riches tale of a young woman sold into prostitution by her penniless mother. “She worked her way up and used the power that she had to get herself out,” explained McEntire. “She’s not ashamed. She did what she had to do to get out.”
01: Shania Twain – You’re Still the One
The best country song of the 90s? That’s a debate, but this one is certainly in the discussion. Shania Twain’s Grammy-winner was co-written with then-husband Robert John ‘Mutt’ Lange. She recalled the writing process: “As I sang the chorus melody repeatedly while working out the lyrics, he kicked in with the counter line, ’You’re still the one,’ and it gave me chills. All of a sudden we had a hit chorus. It was a magic moment.”
Think we missed one of the best 90s country songs? Let us know in the comments below.