The now-22 year old Georgia-born musician also became the first openly gay Black artist to win a Country Music Association award. The track won Lil Nas X Grammy Awards for Best Music Video and Best Pop Duo/Group Performance. 1 song since the debut of the Hot 100 chart. In total, “Old Town Road” spent 19 weeks on top of the Billboard charts-helped by the number of remixes the artist allowed for-becoming the longest-running No. In April, a remix of the song was released with Cyrus. Later, in March of 2019, the song was re-released by Columbia Records after a bidding war. Lil Nas X (born Montero Lamar Hill) released “Old Town Road” on Decem(three years ago, today).