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Hit Parade | Music History and Music Trivia - Ride ’til I Can’t No More Edition Part 1

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…

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