This year’s CMA Awards proved yet another exciting night for country music fans, with artists such as Garth Brooks and Kacey Musgraves taking home major awards. Sure to be among the most discussed awards given last night is that of Musical Event of the Year, which went to Atlanta rapper Lil Nas X and singer Billy Ray Cyrus for this summer’s smash hit “Old Town Road (Remix).”

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 recently reached the top position on Billboard’s Hot Country Songs chart with his song “The Git Up.” Blanco Brown is now included among a limited number of country artists to ever hit 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 only 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.”