20 Country Rap Songs That Preceded ‘Old Town Road’

August 13, 2019 by Charles Stockdale

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Atlanta rapper Lil Nas X recently made music history with his breakout hit “Old Town Road.” The song — which first gained popularity as a meme on video app TikTok — is now the longest running No. 1 hit in the history of the Billboard Hot 100 popular music chart.

And while the song was controversially removed from Billboard’s country music chart following its debut for essentially not being “country” enough, it undoubtedly possesses some qualities common to country music, namely the evocation of cowboy imagery and inclusion of a banjo (derived from a Nine Inch Nails sample). Lil Nas X himself described the song as “country trap,” saying it belongs in both the country and rap genres.

Country trap appears to be having a moment. In addition to the enduring popularity of “Old Town Road,” country trap artist Blanco Brown has held the top position on Billboard’s Hot Country Songs chart for the past five weeks with his song “The Git Up.” If the song’s hot streak continues, it could break Billboard’s record for country song spending the longest amount of time at No. 1. These are the most popular country songs of all time.

The blending of country and rap is not new, however. Artists have combined elements from the two genres for decades, producing quite a few popular songs along the way. And while Lil Nas X’s partnership with country singer Billy Ray Cyrus — who appears on the “Old Town Road” remix — may seem odd, it’s far from the strangest musical collaboration in popular music. These are the most bizarre musical collaborations.

24/7 Tempo has identified 20 country rap songs that preceded “Old Town Road.” Some songs simply feature rappers exploring country or rural themes, some utilize instruments most commonly found in country music, and a few feature traditionally country artists trying their hands at rapping.

Click here to see the country rap songs that preceded “Old Town Road.”

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1. Wild Wild West
> Artist: Kool Moe Dee
> Album: How Ya Like Me Now (1987)
> Spotify plays: 2.6 million

Grammy award-winning rapper Kool Moe Dee dabbled in western imagery more than three decades before Lil Nas X with his single “Wild Wild West.” The song about a rough neighborhood was accompanied by a Western-themed music video. It peaked at No. 62 on the Billboard Hot 100 in 1988.

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2. Square Dance Rap
> Artist: Sir Mix-A-Lot
> Album: Swass (1988)
> Spotify plays: 0.7 million

Before he released his smash hit “Baby Got Back,” Seattle-based rapper Sir Mix-A-Lot released his first single “Square Dance Rap” in 1985. The song, which features the sounds of a high-pitched square dance caller, was later re-released as a part of his debut album “Swass.”

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3. Ghetto Cowboy
> Artist: Mo Thugs Family ft. Bone Thugs-N-Harmony
> Album: Chapter II: Family Reunion (1998)
> Spotify plays: 10.8 million

Mo Thugs Family — a collective led Bone Thugs-N-Harmony — released the single “Ghetto Cowboy” off their second album. The song’s lyrics contain numerous references to Western themes, and its backing beat features samples of horses galloping. The song peaked at No. 15 on the Hot 100 chart in 1999 and reached the top spot on Billboard’s Hot Rap Songs chart.

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4. Cowboy
> Artist: Kid Rock
> Album: Devil Without a Cause (1998)
> Spotify plays: 31.7 million

Kid Rock’s music combines influences from various genres, including rock, rap, and country. All of these can be heard on “Cowboy” from his 1998 album “Devil Without a Cause.” The song opens with a blazing harmonica and slide guitar and features the chorus, “I want to be a Cowboy, baby; ride at night ’cause I sleep all day.”

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5. Wild Wild West
> Artist: Will Smith ft. Dru Hill, Kool Moe Dee
> Album: Willenium (1999)
> Spotify plays: 19.4 million

Will Smith’s song “Wild Wild West” was a huge hit, reaching No. 1 on the Hot 100 during the summer of 1999. The song was originally recorded for Smith’s movie of the same name, and it was then included on his album “Willenium.” While the song does not incorporate the sounds of country music — it heavily samples Stevie Wonder’s “I Wish” — it includes Western lyrical imagery much in the same way that “Old Town Road” does. The song also features rapper Kool Moe Dee, who recorded his own “Wild Wild West.”

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6. I Wanna Talk About Me
> Artist: Toby Keith
> Album: Pull My Chain (2001)
> Spotify plays: 19.9 million

Musician Toby Keith’s “I Wanna Talk About Me” leans further to the country side of country-rap, yet the song’s rhythmically spoken verses give it an undoubtedly hip hop edge. The song, about a guy who wants his turn to talk about himself with his talkative partner, was a big country hit, reaching No. 1 on Billboard’s Hot Country Songs chart and No. 28 on the Hot 100.

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7. Deliverance
> Artist: Bubba Sparxxx
> Album: Deliverance (2003)
> Spotify plays: 18.2 million

Southern rapper Bubba Sparxxx grew up in rural Georgia, a fact that comes through in much of his music. Sparxxx’s 2003 album “Deliverance” is filled with the type of lyrical content that one could find on a country record and also features many of the instrumental sounds, including those of the banjo and fiddle. The album’s title track is among the performer’s most successful songs, reaching No. 22 on the Hot Rap Songs chart.

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8. Over and Over
> Artist: Nelly ft. Tim McGraw
> Album: Suit (2004)
> Spotify plays: 47.2 million

St. Louis-born rapper Nelly teamed up with country superstar Tim McGraw on this song about regretting a breakup. The two artists — who had previously expressed mutual appreciation for one another — not only appeared on the song together, but also co-wrote it. “Over and Over” peaked at No. 3 on the Hot 100.

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9. I Play Chicken With the Train
> Artist: Cowboy Troy ft. Big & Rich
> Album: Loco Motive (2005)
> Spotify plays: 1.5 million

Nashville-based Cowboy Troy is described in his official promotional material as a “six-foot five-inch, hick-hop artist.” The musician teamed up with multi-platinum country duo Big & Rich on this 2005 single, which reached No. 48 on the Hot Country Songs chart. The track features Troy rapping over a full country band.

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10. Boss of tha Stix
> Artist: Big Smo ft. Mr. Sneed
> Album: American Made (2010)
> Spotify plays: 1.0 million

Country rapper Big Smo blends twangy guitar and heavy hip hop drums in his song “Boss of tha Stix.” Smo touches on numerous “country” topics in his lyrics, including biscuits, tractors, moonshine, and old dirt roads.

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11. Dirt Road Anthem (Remix)
> Artist: Jason Aldean ft. Ludacris
> Album: (2011)
> Spotify plays: 5.4 million

Country singer Jason Aldean’s original “Dirt Road Anthem” already had a healthy dose of hip hop in it when it was first released, with Aldean rapping the song’s verses. Its rap credentials were further increased on the remix with the addition of a verse by Georgia rapper Ludacris, whose lyrics include a shout-out to Country Music Hall of Fame inductee Kenny Rogers.

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12. Both of Us
> Artist: B.o.B ft. Taylor Swift
> Album: Strange Clouds (2012)
> Spotify plays: 46.8 million

“Both of Us,” the 2012 single from rapper B.o.B featuring once “country” pop superstar Taylor Swift, highlights the major differences between country and rap. The song, which peaked at No. 18 on the Hot 100, shifts from Swift’s gentle, acoustic guitar-backed vocals to B.o.B’s dubstep-tinged rap verses in an almost jolting way.

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13. Accidental Racist
> Artist: Brad Paisley ft. LL Cool J
> Album: Wheelhouse (2013)
> Spotify plays: 2.1 million

Country singer Brad Paisley teamed up with rapper LL Cool J for this controversial 2013 song that attempts to tackle modern racial issues. While the song has its detractors, it also has plenty of fans who helped it reach No. 23 on the Hot Country Songs chart and No. 77 on the Hot 100.

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14. Cruise (Remix)
> Artist: Florida Georgia Line ft. Nelly
> Album: Here’s to the Good Times… This Is How We Roll (2013)
> Spotify plays: 59.0 million

“Bro-country” duo Florida Georgia Line are among the most prominent acts pushing country in the direction of pop and hip-hop. The remix of their 2012 hit “Cruise” features a rapped verse by Nelly. The song peaked at No. 4 on the Hot 100.

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Source: Rick Diamond / Getty Images

15. Let Your Country Hang Out
> Artist: The Lacs
> Album: Nothing in Particular (2014)
> Spotify plays: 9.0 million

Country rap duo The Lacs, like Cowboy Troy, refer to their sound as “hick-hop.” One of their most popular songs is “Let Your Country Hang Out” from the album “Nothing in Particular,” which charted on both Billboard’s Top Country Albums and Top Rap Albums charts. The ode to country living has 9 million streams on music service Spotify.

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16. Workin’ On
> Artist: Colt Ford
> Album: Thanks For Listening (2014)
> Spotify plays: 32.5 million

Colt Ford, who performed alongside Bubba Sparxxx in the ’90s, is another Georgia native who is active in country rap. Ford is the original performer of “Dirt Road Anthem,” which became a massive hit for Jason Aldean. Ford’s sound is well represented in the single “Workin’ On,” which features the musician rapping alongside the sounds of a violin and steel guitar.

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17. Backroads Life
> Artist: Charlie Farley ft. The Lacs
> Album: Hog Heaven (2014)
> Spotify plays: 6.0 million

Arkansas-based rapper Charlie Farley evokes much of the imagery found in modern country in his country rap song “Backroads Life,” with a chorus that mentions mud-covered tires, ice cold beer, and, of course, backroads. Farley has worked with other country rappers, including Colt Ford and Bubba Sparxxx.

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18. Outlaw (feat. Luke Combs)
> Artist: Upchurch
> Album: Heart of America (2016)
> Spotify plays: 18.0 million

While “Outlaw” may not be rapper Upchurch’s most popular song, it is notable for featuring multi-platinum country musician Luke Combs singing the chorus. The song is a rap version of Combs’ song “Can I Get An Outlaw,” in which he calls for a return to authentic country music, giving as example artists Merle Haggard and Johnny Cash.

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19. Family Don’t Matter
> Artist: Young Thug ft. Millie Go Lightly
> Album: Beautiful Thugger Girls (2017)
> Spotify plays: 18.9 million

Lil Nas X credited fellow Atlanta rapper Young Thug with pioneering “country trap” in Time magazine. Young Thug’s country influences can be heard in his song “Family Don’t Matter” featuring singer Millie Go Lightly. The song includes an acoustic guitar-centered backing track and the occasional call of “yeehaw!” The music video for the song features the rapper donning a cowboy hat and riding horseback.

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20. Fall in the Fall
> Artist: Jelly Roll, Struggle Jennings
> Album: Waylon & Willie 2 (2018)
> Spotify plays: 5.7 million

This dark country rap song is a collaboration between Nashville rappers Jelly Roll and Struggle Jennings, the grandson of country music legend Waylon Jennings. The song is from the 2018 album “Waylon & Willie 2,” which is a reference to the 1978 album “Waylon & Willie” by Waylon Jennings and Willie Nelson.