Kenny Chesney earns 100th entry on Billboard Hot Country Songs with latest single

Kenny Chesney has earned his 100th entry on Billboard Hot Country Songs as his latest single “Carry On” debuts at No. 31 on the May 23 chart.

The song earned 1.5 million U.S. streams, 10.5 million in radio airplay and 2,000 copies sold during the tracking period of May 8-14, according to Luminate. It also opens at No. 20 on Country Airplay, marking Chesney’s 100th entry on that chart as well.

“Carry On” is Chesney’s first single released through the boutique label HEY NOW Records. The company launched this past March, taking on Chesney as their first artist for his upcoming 21st studio album, due later this year.

With his new chart entry, Chesney joins a small group of acts with at least 100 appearances on Hot Country Songs, a chart that dates to 1958. He now has 55 top 10 hits, including 23 No. 1 singles.

On Country Airplay, which began tracking radio in 1990, Chesney’s 100 entries tie him with George Strait. Garth Brooks follows with 93, while Tim McGraw has 91 and Alan Jackson has 82.

Chesney also ranks among the most successful artists in the chart’s history. His 23 Hot Country Songs No. 1s place him 11th overall. His first No. 1 came in 1997 with “She’s Got It All.”

At country radio specifically, Chesney holds the record for the most No. 1 hits with 33 Country Airplay leaders, ahead of Blake Shelton at 30, Tim McGraw at 29, and several artists tied at 26 or fewer.

The milestone arrives during a period of recent career highlights. Chesney recently completed a landmark opening run at Sphere in Las Vegas, becoming the first country artist to headline the venue. Around the same time, Billboard named him its Top Country Artist of the 21st Century, recognizing performance across singles and albums. He was also named a 2025 Country Music Hall of Fame electee.

“All I was ever trying to do was find the best possible songs, things that spoke to the heart of how No Shoes Nation lives,” said Chesney, “and then taking that music, those albums that were slices of my life out to everyone who wanted to come out, be a part of the shows, the moments and the memories we made in every city we played.”

“Kenny Chesney rules as the No. 1 country act on Billboard’s recap of the first 25 years of the 21st century,” Billboard’s Jim Asker wrote in the publication’s 21st-century ranking overview.

Asker added that Chesney’s 17 No. 1s on the weekly Top Country Albums chart and his 20 (of 23 total) No. 1s on Hot Country Songs are the highest numbers among all artists in those years.