My Top 100 Country Singles of the 1990s
I already did lists of my top 100 R&B, pop, rock and rap singles of the 1990s, but I saved country as my last genre of the decade to cover since it was the one I had to go back and do the most listening for to catch up on what I missed. I lived in Sussex County, Delaware for most of the '90s (like contemporary country star Jimmie Allen!) and heard a fair amount growing up, but I never really embraced it or found the country that I loved until I got a little older. So this was harder than making my country lists for the 2000s and the 2010s, but I feel good about the list I wound up with, I think I summed up "'90s country" in the mainstream view pretty well but also incorporated some stuff that really shows the range and depth of the genre in that era. Here's a Spotify playlist with every song (except for the Garth Brooks songs, since his catalog streams exclusively on Amazon).
1. Alan Jackson - "Chattahoochee" (1993)
For most of the '90s, The Box, the channel formerly known as the Video Jukebox Network, was a chaotic alternative to MTV that exclusively played music videos requested by viewers, who'd pay a couple bucks to call into a 1-900 number. This experiment in democracy largely resulted in a pretty gangsta rap-heavy playlist on The Box in the area where I watched it (I believe you got different videos depending on where you lived). But other genres occasionally elbowed their way in, and Alan Jackson's "Chattahoochee" was the only country video I'd see on there all the time, for months and months, as much as Snoop and Dre.
2. Brooks & Dunn - "Neon Moon" (1992)
Spoiler alert, no album has more songs on this list than Brooks & Dunn's smash hit debut Brand New Man. And "Neon Moon" just went viral last year on TikTok, giving it an even longer shelf life than some of the duo's other songs that crossed over more at the time.
3. Shania Twain - "Man! I Feel Like A Woman" (1999)
Shania Twain's third album, and second blockbuster with producer and then-husband Mutt Lange, Come On Over, is an insane hitmaking achievement: 12 of its 16 songs were released as singles, and the 8th single, "Man! I Feel Like A Woman," is arguably its most famous and enduring track now (making Mutt Lange's previous biggest commercial achievement, the 7 singles from Def Leppard's Hysteria, almost seem like small potatoes by comparison). But I like that that big twangy riff at the center of the track is arguably the most country thing out of Twain's most pop-leaning hits.
4. Dwight Yoakam - "A Thousand Miles From Nowhere" (1993)
Dwight Yoakam can do no wrong in my eyes, I think he's probably the greatest country artist of his generation. And though he notched his only country radio #1s in the '80s, his best selling album was 1993's triple platinum This Time, which had three #2 singles including "A Thousand Miles From Nowhere," before Yoakam and the neotraditionalist sound he epitomized started to disappear from country radio.
Dwight Yoakam can do no wrong in my eyes, I think he's probably the greatest country artist of his generation. And though he notched his only country radio #1s in the '80s, his best selling album was 1993's triple platinum This Time, which had three #2 singles including "A Thousand Miles From Nowhere," before Yoakam and the neotraditionalist sound he epitomized started to disappear from country radio.
5. John Michael Montgomery - "Sold (The Grundy County Auction Incident)" (1995)
The most famous song John Michael Montgomery recorded was the original "I Swear," later turned into a massive crossover hit by the R&B group All-4-One. But I much prefer this fast talkin' banger that verges on a novelty song but is also a really clever, tightly composed love song.
6. Garth Brooks - "Friends In Low Places" (1990)
1989's Garth Brooks went gold in August 1990, the same month Brooks released the lead single from his second album, and within a few months both albums would be multiplatinum and eventually diamond, and he was off to the races as the biggest star country music had ever seen. Honorable mention to the 8-minute live version.
7. Reba McEntire - "Is There Life Out There" (1992)
Reba McEntire excels at communicating a narrative in a song, uphold country's storytelling tradition both in her hit '90s covers of decades-old classics "Fancy" and "The Night The Lights Went Out In Georgia" and in her originals. "Is There Life Out There" is a song about a woman who married young and feels some kind of vague longing for something besides being a wife and mother (in the video she's also an overworked waitress studying for a college degree, and her loving husband is played by Huey Lewis). There's no big moment of action or feminist awakening, but McEntire makes it a gripping capsule drama with the sheer force of her voice and personality, and the drum fills on that outro are real Nashville session musician excellence. Two years after the song topped the country charts, McEntire starred in a TV movie on CBS based on the song (also called Is There Life Out There? but with no Huey Lewis), foreshadowing her future as a network TV star.
8. Martina McBride - "Independence Day" (1994)
"Independence Day" is another story song about a wife who's not content with her life, but it's a little more explicitly about her gaining her freedom from an abusive husband (Reba McEntire was offered the song and turned it down). Right wing moron Sean Hannity used the song as the theme song to his radio show for over a decade as if it were simply a patriotic anthem, but songwriter Gretchen Peters just donated her royalties from the show to liberal causes.
9. George Strait - "Blue Clear Sky" (1996)
George Strait has 44 number one songs on Billboard's Country Songs chart, the most by any country artist as well as the most number ones by any artist in any radio format, 18 in the 1980s and 17 in the 1990s. He settled into a good ballad groove in the '90s, but I think the gentle uptempo "Blue Clear Sky" is my favorite of his '90s hits, with some gorgeous pedal steel work. Apparently co-writer Bob DiPiero heard Tom Hanks say "blue clear sky" instead of the more commonplace phrase "clear blue sky" in Forrest Gump, and it stuck in his head enough to write a song.
10. Joe Diffie - "Prop Me Up Beside The Jukebox (If I Die)" (1993)
I didn't know Joe Diffie's music too well before he became one of the music world's first casualties of COVID-19 in the spring of 2020, and sitting at home while the world shut down, I put together a Joe Diffie deep album cuts playlist and became an instant fan. Great vocalist, and in "Prop Me Up Beside The Jukebox" he'd already recorded the song that would be his fittingly lighthearted epitaph.
11. The Chicks - "There's Your Trouble" (1998)
The (formerly Dixie) Chicks plugged along for about six years as a low profile bluegrass band whose career highlight was appearing on A Prairie Home Companion. But then Lloyd Maines, a steel guitarist who played on the group's early independent albums, introduced them to his daughter Natalie, who became their new lead singer, and they took off fast, becoming the biggest selling female country band of all time with their major label debut Wide Open Spaces.
12. Alabama - "I'm In A Hurry (And Don't Know Why)" (1992)
One thing that bums me out is how much vocal groups have fallen out of favor across popular music in my lifetime, I miss hearing big rich harmonies in R&B and pop and especially country as things moved more towards solo stars. But Alabama, who boasted some of country's best harmonies, had a big hitmaking run in the '80s than ran well into the '90s with a few classics.
13. Trisha Yearwood - "She's In Love With The Boy" (1991)
Definitely one of the best songs about young love that features a brief vignette that takes place outside a Tastee-Freez. I always wonder if that line in the Yearwood song was a deliberate homage to John Mellencamp's "Jack & Diane."
14. Wynonna - "No One Else On Earth" (1992)
Vocal duos have been big in country for a long time, sometimes they were sibling acts, but The Judds are probably the only mother/daughter duo that became major stars. After a big '80s run, though, Naomi Judd took a step back due to health issues, and Wynonna Judd went solo and became a mononym star with some killer singles.
15. Toby Keith - "Should've Been A Cowboy" (1993)
By the end of the '90s, Toby Keith had made "How Do You Like Me Now?" and struck on the bigger, bolder persona that made him one of the best (and most divisive) country hitmakers of the 2000s. But he had a really good run in the '90s with a classic debut single that introduced Toby 1.0 perfectly.
16. Dolly Parton - "Silver And Gold" (1990)
Dolly Parton is probably more beloved now, in 2023, than she's ever been in her long career, but 1989's White Limozeen and 1990's Eagle When She Flies represent her last run as a country radio hitmaker. And "Silver Of Gold" was also one of the last hit songs penned by Carl Perkins of "Blue Suede Shoes" fame.
17. Vince Gill - "Don't Let Our Love Start Slippin' Away" (1992)
The video for Vince Gill's most enduring single was crammed full of cameos by big name musicians playing Gill's backing band (Michael McDonald, Carl Perkins, Leon Russell, etc.), but Reba McEntire is also in there reprising her waitress character from the "Is There Life Out There" video.
18. Travis Tritt - "Here's A Quarter (Call Someone Who Cares)" (1991)
One of those bumper sticker country songs where you pretty much get the gist of the whole thing in the title, but it's one of the best of 'em all.
19. Jo Dee Messina - "Heads Carolina, Tails California" (1996)
I didn't even mean to set it up this way, but here we go from a song about a coin to a song about a coin flip. Jo Dee Messina's debut single was blocked from #1 on country radio by a Brooks & Dunn song that will appear later on this list. But last year, Cole Swindell's homage "She Had Me At Heads Carolina" hit #1, and Messina appeared on a remix and performed with Swindell at the CMAs.
20. George Strait - "I Just Want To Dance With You" (1998)
John Prine became a songwriting legend on Chicago's folk scene, and his songs were occasionally turned into minor country hits by David Allen Coe and Lynn Anderson, while people like Johnny Cash and Kris Kristofferson sang his praises. Prine moved to Nashville in 1980 largely out of his love and admiration for country music, but ran a small independent label and seemed to only casually engage in Music Row songwriting sessions. And then in 1998, one of Prine's songs from 1986 German Afternoons became a bona fide country radio #1 thanks to a lovely recording by George Strait.
21. Montgomery Gentry - "Lonely And Gone" (1999)
As John Michael Montgomery's reign as a hitmaker was winding down in the late '90s, his older brother Eddie Montgomery formed a group with Troy Gentry and they embarked on a run of southern rock-inspired hits that I enjoyed even more. Sadly, Gentry died in a helicopter crash in 2017.
22. Alison Krauss & Union Station - "When You Say Nothing At All" (1995)
Keith Whitley was one of country's most promising new stars when he died of alcohol poisoning in 1989; "When You Say Nothing At All" was one of three country radio #1s he released in his lifetime, followed by two more posthumous #1s. A few years later, Whitley's widow Lorrie Morgan organized a tribute album, and Alison Krauss put "When You Say Nothing At All" back on the charts and took it to #3. For a few years, Krauss was the most awarded woman in Grammy history, a distinction now held by Beyonce, but she's only had four top 10 hits on country radio, and "When You Say Nothing At All" is the only one that's not a duet.
23. Billy Ray Cyrus - "Could've Been Me" (1992)
Billy Ray Cyrus was a massive flash in the pan, with a 9x platinum debut that never really carried any momentum into his subsequent albums once it was clear that he only had one "Achy Breaky Heart" (and thank god for that). And then, against all odds, he became a pop culture fixture throughout the 21st century, first as the father and co-star of massive TV and pop music sensation Miley Cyrus, and then with the remix that turned Lil Nas X's "Old Town Road" into the Hot 100's longest running #1 of all time
24. Brooks & Dunn - "Boot Scootin' Boogie" (1992)
Since I find "Achy Breaky Heart" too embarrassing to include on the list, I will happily let "Boot Scootin' Boogie" stand as the definitive song of the early '90s moment when line dancing went mainstream.
25. George Jones - "Honky Tonky Song" (1996)
George Jones made some of the greatest country hits of the '50s, '60s, '70s and '80s, a truly remarkable run. But he finally started to fall out of favor with country radio in the '90s and was often cantankerous about it. One of his few memorable '90s singles riffed playfully on the legendary story of Jones driving a riding mower down the highway to the liquor store in the '70s, after his wife Tammy Wynette hid the keys to his car.
26. Joe Diffie - "New Way (To Light Up An Old Flame)" (1991)
Diffie was the most dutiful George Jones disciple of country's newer stars in the '90s, and was one of the many guests on Jones's defiant 1992 single "I Don't Need Your Rockin' Chair." But "New Way (To Light Up An Old Flame"is really the greatest example of Diffie showing that he could not only sing uncannily like the Possum but also write a song that sounds like one of his '70s classics.
27. Mary Chapin Carpenter - "Passionate Kisses" (1993)
Lucinda Williams had a minor hit with the original "Passionate Kisses" in 1988, and eventually won a Grammy for it after a cover became Mary Chapin Carpenter's biggest hit in 1993, though Williams wouldn't really become a star in her own right until 1998's acclaimed Car Wheels On A Gravel Road. Chapin Carpenter's version was one of the only songs on this list that I remember hearing a lot when it was new, it must have crossed over to MTV or VH1 way more than other country hits of the era.
28. Garth Brooks - "Two Of A Kind, Workin' On A Full House" (1991)
Before he became a big name in southern rock with Gov't Mule and The Allman Brothers Band, Warren Haynes kicked around as a country session guy and sideman, co-writing "Two Of A Kind" with Dennis Robbins. The original Robbins recording made a tiny splash on the charts in 1987, and then caught the ear of a young Garth Brooks, who decided to cut it early into his ascent to superstardom.
29. Kenny Chesney - "How Forever Feels" (1998)
Tim McGraw was the first artist to cut "How Forever Feels," but he decided not to release it. Instead, Kenny Chesney wound up releasing the song and it became his second #1 hit. And its first verse, with lyrics referencing the beach, margaritas and Jimmy Buffett, pointed the way towards the beach bum "no shoes nation" persona that would define Chesney when became one of the most consistently successful country singers of the 21st century.
30. Reba McEntire and Linda Davis - "Does He Love You" (1993)
Linda Davis released several solo singles that dwindled around the lower reaches of the country charts in the late '80s and early '90s when she took a gig singing backup with Reba McEntire's touring band. And when Reba McEntire decided to record "Does He Love You," a two-woman duet about a love triangle, she decided to sing it with Davis instead of one of the more established stars her label pushed for. The song became a massive hit anyway, helping boost Davis's solo career, and Davis's daughter Hillary Scott later became a major star with Lady A(ntebellum).
31. Shania Twain - "Whose Bed Have Your Boots Been Under?" (1995)
After an unsuccessful debut album, Shania Twain rebooted her career (no pun intended) with the Mutt Lange-produced album, The Woman In Me, that would make her a superstar. "Whose Bed Have Your Boots Been Under?" was sort of a soft launch, the most overtly country song on the album but not nearly as a big a hit as the singles that would follow, but I think it's absolutely one of her best.
32. Willie Nelson - "Ain't Necessarily So" (1990)
Willie Nelson released Born For Trouble and its single "Ain't Necessarily So" about a month before the IRS raided his ranch and seized his assets, altering the course of Nelson's life and stalling his momentum as a hitmaker on the country charts. But of course, he survived and went on to make dozens of more great albums, even if he mostly disappeared from the radio.
33. Mindy McCready - "Guys Do It All The Time" (1995)
I didn't know much about Mindy McCready, I knew her name when she was making hits in the '90s and I remember hearing when she'd died in 2013. But I wasn't prepared for the roller coaster ride of looking at her Wikipedia page: McCready debuted at 20 years old and had several hits, and then had a pretty serious drug problem, with a series of arrests, overdoses, hospitalizations, and suicide attempts. One boyfriend was arrested for attempting to murder her, another sold a sex tape of her to Vivid Entertainment, another committed suicide in her home, and it was alleged that Roger Clemens had an affair with her while she was a teenager. And then in 2013, she committed suicide. A terribly sad story, but she left behind some excellent music.
34. Brooks & Dunn - "My Maria" (1996)
Sometimes Ronnie Dunn's vocals are just to over-the-top to me, but he really hits some great high notes in this song.
35. Jo Dee Messina - "Bye, Bye" (1998)
My first job was at a Greek restaurant in 1998 and 1999, washing dishes and busing tables. And we mostly listened to R&B radio in the kitchen, but out in the dining room a country station would be playing. And the singles from Jo Dee Messina's I'm Alright are songs that always stick out in my memory from those days -- I thought "I'm Alright" was a little too irritatingly bright and chipper, but "Bye, Bye" is a great song.
36. Tracy Byrd - "Watermelon Crawl" (1994)
I've never met a man named Tracy, but apparently enough baby boys were named Tracy in the south in the 1960s that three of them became country stars in the 1990s: Tracy Lawrence, Tracy Byrd, and Tracy "Trace" Adkins.
37. Patty Loveless - "You Don't Even Know Who I Am" (1995)
Another beautifully evocative song about the end of a marriage written by Gretchen Peters, who also penned Martina McBride's "Independence Day." It was announced on Monday, by the way, that Patty Loveless is one of this year's inductees into the Country Music Hall of Fame.
38. Dwight Yoakam - "Turn It On, Turn It Up, Turn Me Loose" (1990)
I love Dwight Yoakam's guitar tone, especially on this song, the lead single from 1990's If There Was A Way.
39. Rhett Atkins - "That Ain't My Truck" (1995)
"That Ain't My Truck" was one of only a couple of top ten hits Rhett Atkins notched as a solo artist. But he's written dozens of hits for others, including his son Thomas Rhett, who became a massive star in 2013.
40. Terri Clark - "Poor, Poor Pitiful Me" (1996)
Linda Ronstadt made Warren Zevon's "Poor, Poor Pitiful Me" into a top 40 hit, but I think I like Terri Clark's take even more, it just works so well as a country song.
41. Brad Paisley - "He Didn't Have To Be" (1999)
When it comes to Brad Paisley, I mostly prefer his uptempo guitar hero songs. But he's great at tearjerking ballads too, and his only '90s hit is one of his best.
42. Garth Brooks - "The Thunder Rolls"
The most enduring Garth Brooks hit that he had a hand in writing, though he initially pitched it to Tanya Tucker before deciding to record it himself. It's a little funny to think of how timid the country industry was at the time that TNN banned the video because of its domestic violence storyline.
43. Sara Evans - "The Cryin' Game"
"Sudes In The Bucket" was my #1 country single of the 2000s but most of the other songs Sara Evans is famous for are schmaltzy ballads. I wish more of her uptempo songs like "The Cryin' Game" were bigger, I love that syncopated acoustic strumming that comes in on the final verse.
44. Travis Tritt featuring Little Feat - "Bible Belt" (1992)
Little Feat, one of my favorite bands of all time, have a lot of country in their sound and their history: they've recorded with Emmylou Harris, Brooks & Dunn, and Brad Paisley, and "Dixie Chicken" was covered by Garth Brooks, and inspired The Dixie Chicks' name. But the only time Little Feat ever touched the country charts was when their Travis Tritt collaboration appeared on the My Cousin Vinny soundtrack.
45. Lyle Lovett - "Don't Touch My Hat" (1996)
In the '90s, Lyle Lovett was married to Juila Roberts for a few years, and I remember it being fashionable to poke fun at one of the most beautiful and glamorous movie stars in the world marrying an ordinary-looking country singer of minor renown. But then at some point I realized that Lyle Lovett makes fantastic music, so I feel bad about all those hacky late night monologue jokes at his expense.
46. Neal McCoy - "No Doubt About It" (1994)
Country music was possibly even whiter in the '90s than in other eras, since Charley Pride was no longer making hits and Darius Rucker hadn't gone country yet. One notable exception is Filipino American singer Neal McCoy, who notched a couple of platinum albums in the mid-'90s.
47. Faith Hill - "Wild One"
Most of the country stars that crossed over to the pop world in the '90s did so with irresistible songs that fit their voices and personalities, but Faith Evans's crossover hits always felt unbearably bland and forced. I much prefer her more earnest and country-leaning material, both from her first two albums and from her later records.
48. Katty Mattea - "455 Rocket" (1997)
Gillian Welch and David Rawlings wrote "455 Rocket" which became a radio hit for Katty Mattea a year after Welch's debut album Revival made her a critical darling and Grammy nominee. Mattea also deserves some props for risking her country career to become a vocal AIDS activist in the early '90s.
49. Emmylou Harris - "High Powered Love" (1993)
1993's Cowgirl's Prayer was the last time Emmylou Harris got played on country radio, but it was a lot less airplay than she'd enjoyed in the '70s and '80s. And with her next album, 1995's Wrecking Ball, she reinvented her sound beautifully and started a new chapter of her career with producer Daniel Lanois.
50. LeAnn Rimes - "Blue" (1996)
LeAnn Rimes was probably the first artist born in the '80s to become a major star, and she sounded almost unbelievably good as a 14-year-old singing a song written in 1958 on her breakthrough hit.
51. Brooks & Dunn - "Brand New Man" (1991)
52. Trisha Yearwood - "How Do I Live" (1997)
53. Martina McBride - "A Broken Wing" (1997)
54. Suzy Bogguss - "Drive South" (1992)
55. Little Texas - "What Might Have Been" (1993)
56. Garth Brooks - "The Dance" (1990)
57. Vince Gill - "Go Rest High On That Mountain" (1994)
58. Lorrie Morgan - "What Part Of No" (1992)
59. Joe Diffie - "Pickup Man" (1994)
60. George Strait - "Easy Come, Easy Go" (1993)
61. David Ball - "Thinkin' Problem" (1994)
62. Hal Ketchum - "Small Town Saturday Night" (1991)
63. Shania Twain - "Any Man Of Mine" (1995)
64. Dwight Yoakam - "Fast As You" (1993)
65. Brooks & Dunn - "My Next Broken Heart" (1991)
66. Randy Travis - "If I Didn't Have You" (1992)
67. Tim McGraw - "Don't Take The Girl" (1994)
68. The Chicks - "Ready To Run" (1999)
69. Clint Black - "A Good Run Of Bad Luck" (1994)
70. Tanya Tucker - "Down To My Last Teardrop" (1991)
71. Garth Brooks - "Callin' Baton Rouge" (1994)
72. Daryle Singletary - "Too Much Fun" (1995)
73. Toby Keith - "You Ain't Too Much Fun" (1995)
74. Reba McEntire - "You Lie" (1990)
75. Faith Hill - "Take Me As I Am" (1993)
76. Waylon Jennings - "Wrong" (1990)
77. Shenandoah - "The Moon Over Georgia" (1991)
78. Patty Loveless - "I Try To Think About Elvis" (1994)
79. Joe Diffie - "John Deere Green" (1993)
80. Pam Tillis - "Maybe It Was Memphis" (1991)
81. Shania Twain - "That Don't Impress Me Much" (1999)
82. George Strait - "Check Yes Or No" (1995)
83. Wynonna - "Tell Me Why" (1993)
84. Garth Brooks - "Ain't Goin' Down (Til The Sun Comes Up)" (1993)
85. Mindy McCready - "Ten Thousand Angels" (1996)
86. Dwight Yoakam - "It Only Hurts When I Cry" (1992)
87. Montgomery Gentry - "Hillbilly Shoes" (1999)
88. Sawyer Brown - "Six Days On The Road" (1997)
89. The Chicks - "Wide Open Spaces" (1998)
90. Alabama - "Jukebox In My Mind" (1990)
91. Travis Tritt - "I'm Gonna Be Somebody" (1990)
92. Diamond Rio - "Meet In The Middle" (1991)
93. Alan Jackson - "Don't Rock The Jukebox" (1990)
94. David Lee Murphy - "A Party Crowd" (1995)
95. Garth Brooks - "Rodeo" (1991)
96. Chad Brock - "Ordinary Life" (1998)
97. Trace Adkins - "(This Ain't No) Thinkin' Thing" (1996)
98. George Strait - "If I Know Me" (1991)
99. Deana Carter - "Strawberry Wine" (1996)
100. Reba McEntire - "Rumor Has It" (1991)
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