Songs With the Most Weeks at No. 1 on the Hot 100 in the 21st Century

Two songs that deftly blend country and hip-hop influences reign as the longest-leading No. 1s on the Billboard Hot 100 chart over the first 25 years of the 21st century – and all-time: Lil Nas X’s “Old Town Road,” featuring Billy Ray Cyrus, and Shaboozey’s “A Bar Song (Tipsy).” The former reigned for a record-breaking 19 weeks in 2019, while the latter matched the mark in 2024.

“‘Old Town Road’ came after a period of feeling like I was out of options,” Lil Nas X said in 2019. “I was living with my sister. She was pretty much fed up with me being there. That’s where the chorus lyric came from – it was me saying, ‘I want to leave everything behind.’ But during the month of me making [it], I gave it a different meaning, so that the ‘old town road’ would be the symbol for success. The horse would be not having too much, but having what you have, in order to get to where you’re trying to go.”

“A Bar Song (Tipsy)” reworks J-Kwon’s 2004 hit “Tipsy.” “My two producers picked up the guitar, started playing the chords and then we started writing it,” Shaboozey recalled late in 2024. “I sang, ‘They know me and Jack Daniels got a history …’ ” J-Kwon then helped clear the sample for “Tipsy.” “It was definitely a lightning-in-a-bottle thing,” Shaboozey said.

As Billboard celebrates the top-performing artists, albums and songs of the first 25 years of the century since 2000, browse below the songs with the most weeks at No. 1 on the Hot 100 in that span.

Plus, check out Billboard’s Top Hot 100 Songs of the 21st Century chart, Top Artists of the 21st Century chart and Top Billboard 200 Albums of the 21st Century chart, as well as all coverage of Billboard’s 21st Century charts here.

Billboard’s Top Artists, Top Billboard 200 Albums and Top Hot 100 Songs of the 21st Century recaps reflect performance on weekly charts dated Jan. 1, 2000, through Dec. 28, 2024. The Top Artists category ranks the best-performing acts in that span based on activity on the Billboard 200 and Hot 100. (Titles released prior to mid-1999 are excluded, although such entries that appeared on the Billboard 200 or Hot 100 in that span contribute to the calculation of the Top Artists chart.)