The 25 Greatest Country Songs of the 90s

Dwight will look a lot like Mick Jones by 2013

As rap and grunge music became more popular in the early ‘90s, a large white audience shifted away from Top 40 and contemporary rock music toward country radio. Nobody benefited more from this than Garth Brooks, who combined arena rock inspired concert performances with corn syrup Okie vocal mannerisms. As the decade went on, hit machines like Faith Hill and Shania Twain sounded more like pop stars than traditional Nashville acts. Yet, there were plenty of instances when traditionalism and commercialism wedded blissfully.

25. “Walls Can Fall,” George Jones. George had been phased out of the charts for the most part by the ‘90s, his biggest solo hit of the decade was the weak identity group stab “High Tech Redneck” and this title track from a solid 1992 album didn’t make the Top 100. However, the greatest singer in the genre’s history could still make excellent music. Others to seek out – “Choices,” “Angel’s Don’t Fly,” and “The Wild Irish Rose.”

24. “Down at the Twist and Shout,” Mary Chapin Carpenter. Ivy league grad Carpenter didn’t completely cut loose on this zydeco inspired number, she seems like the type of woman that spends every Sunday rearranging her sock drawer. Nonetheless, she did take Lucinda William’s “Passionate Kisses” to #4 on the country charts and picked up a Grammy with this catchy number.

23. “Is There Life Out There,” Reba McEntire. Reba is my distaff George Strait, a traditionalist that scored huge hits for decades, most of which do absolutely nothing for me. This song is the country version of The Kinks, “Oklahoma U.S.A.” – a depressed young married woman ponders what other possibilities life could have held for her. Pair this one up with Martina McBride’s “Independence Day” for your own Lifetime Network ’90s country female empowerment movie.

22. “Third Rock from the Sun,” Joe Diffie. Diffie wasn’t bigger than the Beatles in the 90s, but his fine honky tonk voice carried him through some questionable material (“John Deere Greene,” “Pickup Man”). If this Hendrix titled tale of police chief barroom cheating is too kitschy for you, give “If the Devil Danced (In Empty Pockets)” a spin.

21. “Here’s a Quarter (Call Someone That Cares),” Travis Tritt. Tritt’s ego always seemed outsized for his talent, but this is a classic country kiss off. According to his biography, which I’ll never read, Tritt penned this one the same evening he received divorce papers from his second wife.

20. “If I Didn’t Have You,” Randy Travis. Travis was the biggest star of country music in the late ‘80s. He started the ‘90s strong, was eventually eclipsed by Garth Brooks, but still charted sixteen Top Ten hits and five #1s, including this one. Just hand the guy a good song and his voice will do the rest.

19. “Past the Point of Rescue,” Hal Ketchum. Ketchum performed in upstate New York as a teenager, and then transitioned to the Texas dance hall scene before hitting Nashville. If this haunting chronicle of unrequited love doesn’t grab you, check out “Small Town Saturday Night” or his cover of The Vogues’ “Five O’Clock World.”

18. “Friends in Low Places,” Garth Brooks. Garth’s penchant for melodramatic overstatement (“The Dance,” “The Thunder Rolls,” “We Shall Be Free”) is always hard to take on empty stomach. You have to give this advertising major credit for understanding how country music was evolving in the early ‘90s and filling a commercial void. “Friends in Low Places” was both a good song and effective image making. He also had the intuitive sense to make his fortune and walk away versus fighting a losing battle for sustained relevance.

17. “Gone Country,” Alan Jackson. I limited this list to no more than three songs per artist or every other entry would have been Alan Jackson and John Anderson. On the sneering “Gone Country,” Jackson, though songwriter Bob McDill, notes how ‘90s Nashville was being flooded with musicians from all different genres to try to milk the cash cow. Feel free to pretend that “Chattahoochie” is in this slot if you like it more.

16. “Go Rest High on That Mountain,” Vince Gill. According to my wife and daughter, Vince Gill and I have a physical resemblance, although I don’t want to play Crisco twister with Amy Grant. However, I wish I had that voice. Vince wrote this eulogy/tribute, inspired by the deaths of Keith Whitley and Vince’s brother Bob, and belts it out with stirring beauty.

15. “Drive South,” Suzy Bogguss. Aledo, Illinois native Bogguss brought a kittenish girl next door beauty to country music in the early ’90, while the John Hiatt lyric “We could go down with a smile on/Don’t bother to pack your nylons” pushed the limits for Nashville sexuality. I was personally sent on a goodwill mission involving Suzy last year and she remains both charming and gracious.

14. “It Only Hurts When I Cry,” Dwight Yoakam. Dwight was the hot young stud of country music in 1986, with music tough enough for the guys and jeans tighter than tight enough for the ladies. His had a fantastic singles run in the early ‘90s and this co-write with “King of the Road” Roger Miller, to quote Yoakam biographer Don McLeese, “holds its own with the best songs of either.”

13. “Money in the Bank,” John Anderson. A delightfully humorous love song/rocker that John knocks out of the park with his phrasing and energy. When Anderson goes to #1 with a song like this, which he did in 1993, then everything is right in the world.

12. “Hard Rock Bottom of Your Heart,” Randy Travis. Cheating, regretting, singing incredibly well about it.

11. “Cowboy Take Me Away,” Dixie Chicks. A romantic dream at the intersection of love and escapism. Pretty, pretty, pretty.

10. “Here in the Real World,” Alan Jackson. Jackson’s first hit was a tear jerker heartbreak tale of unrequited love against the backdrop of cinema story book endings. Feel free to pretend that “Little Man” is in this slot if you like it more.

9. “Wide Open Spaces,” Dixie Chicks. One of the most polarizing acts in the history of country music, the Dixie Chicks were originally viewed by some music fans as a manufactured act, a country version of the Spice Girls, due to their blonde on blonde cutesy image. Then, of course, Natalie Maines got too mouthy for country radio. In any event, for a small period of time, the DCs spoke to a large audience of young women not unlike the relationship that Taylor Swift has with her fanbase today. And, they were very good.

8. “Heartland,” George Strait. Goodness gracious, somebody either put speed in his Geritol or actually woke George up for this recording. He sounds suspiciously alive! Just when one thinks they never want to hear another song about the superiority of rural life to the evil city ways, this slams in your speakers to break down all resistance. Oh, and check out the movie Pure Country where Mr. Charisma dons a PONYTAIL!

7. The Band Plays On, John Anderson. An album track from 1996 that nobody has heard, John duets with Levon Helm on this number that will absolutely rip your heart of its chest cavity, slam it on the driveway, then stomp a mudhole in it. It doesn’t matter what happens to you in life. The band still plays on.

6. “He Thinks He’ll Keep Her,” Mary Chapin Carpenter. Country music has never been a hotbed of raging feminism, it’s more defined by “Stand by Your Man” than “The Pill,” but on this def rap MC Carpenter spits out some dope lyrics about a unsatisfied Stepford wife that left seeming domestic bliss for the satisfaction of a low paying clerical job. Maybe she should go to beauty school.

5. “Don’t Rock the Jukebox,” Alan Jackson. Pretty much a perfect country song, isn’t it?

4. “Strawberry Wine,” Deana Carter. Ace songwriter Matraca Berg co-wrote this monster hit based upon her real life experience of losing her…um…cell phone…or something. Woke last night to the sound of thunder. How far off I sat and wondered.

3. Seminole Wind, John Anderson. An evocative classic, filled with rich imagery, penned solely by John David Anderson. The beauty of this song rolls over you like tidal waves. Osceola cried when this peaked at #2 in 1992.

2. When You Say Nothing at All, Alison Krauss. Krauss released her first album at the age of fourteen and has won 27 Grammy awards. Things to love about this song – Alison’s fragile yet beautiful voice, the perfect arrangement, and the simple message of love. Man, I’d better grab a beer and watch some NASCAR before I get teary-eyed.

1. “A Thousand Miles from Nowhere,” Dwight Yoakam. Put this material in the wrong hands and it could become comically bad self-pity. Match it up with Pete Anderson’s yeoman guitar work and production, and Dwight’s itemization of betrayal and loneliness becomes vividly palpable. Smashing. Majestic. Not bad at all.