When it crash-landed on the charts in 2019, Lil Nas X’s “Old Town Road” felt new and old at the same time: a savvy, TikTok-fueled viral hit that summarized a century of cross-cultural collisions between R&B, rap and country. It was also unexpectedly huge—a record 19 weeks at No. 1 on the Hot 100—and controversial, as Billboard magazine pulled the song from its Hot Country Songs chart, prompting a reckoning on race and the very definition of country music.

“Old Town Road” wasn’t just a reckoning—it was a culmination. As a hard-to-categorize hit, it called back to cross-genre experiments by everyone from Ray Charles and the Rappin’ Duke to Bubba Sparxxx and even Jason Aldean. As a viral smash, its antecedents date back to “The Twist,” right through “Crank That (Soulja Boy)” and “Harlem Shake.”

In honor of his new book Old Town Road (now in bookstores!) join Chris Molanphy as he walks through the many predecessors to “Old Town Road” and explains why can’t nobody tell Lil Nas X nothin’.

Podcast production by Kevin Bendis.

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