Having spent a career looking for songs that connected people to the key moments in their life, Kenny Chesney’s recorded many of the 21st century’s most defining country hits. With “Carry On,” his HEY NOW Records debut, the East Tennessee songwriter-superstar tapped into a simple life philosophy that’s not just topped the Country Aircheck/Mediabase chart for the second week, but hit No. 1 on Billboard’s Country Airplay chart.

“As a creative spirit, sending songs into the universe that hit people in the heart means everything to me,” Chesney tells Billboard. “That ‘Carry On,’ as my 100th [charted] single, has had so many big moments is humbling. But what really matters is that it’s connecting with people who hear their lives in my music. It’s an honor and privilege. Even more, it’s so much fun to see people’s faces when they’re singing that chorus: ‘If it feels good do it.’”

Even more than feeling good, the bartender wisdom – served over a lilting midtempo with a Caribbean breakdown for the bridge – has resonated with the fans. Set in Key West’s historic Schooner Wharf, written by Jessi Alexander, Matt Jenkins and Chase McGill, “Carry On” became Chesney’s 100th charting single, set a record for most Top 10s (62) and extended his run as the most No. 1s on the chart, established in 1991.

Produced with longtime collaborator Buddy Cannon, “Carry On” delivers a freshness and empowerment that hit No. 1 in just 21 weeks! As Ross on the Radio’s Sean Ross wrote, “Country also had its summer comeback vehicle in Kenny Chesney’s ‘Carry On.’”

Following “Carry On” with the sweeping “Remember Me That Way,” a potent perspective-definer that suggests how we frame what was can be as important as how we embrace the moments in real time, Chesney delivers a song that Music Row praises for its “dreamy vibe,” while praising the performance as “clear and true.”

“It felt like the right place to go after ‘Carry On,’” Chesney explains. “Both songs really create life philosophies without preaching. How you see things sometimes allows you to remember what was so good, how to really appreciate every moment – and not get lost in what doesn’t really matter in the end.

“When we sang it at the Pinnacle, even as new as ‘Remember Me’ was, you could feel the people who were singing along really putting themselves into that chorus. You could see it on their faces – that they were in those moments – and there’s real freedom in that.”

Whether catharsis or appreciation, “Remember Me That Way” delivered 151 first week adds, the most of Chesney’s career after “Carry On” locked the entire panel its first week.

By the time the Original Vibe Room Tour 2027 hits Tampa’s Raymond James Stadium on April 24, the song will have built into a full-tilt anthem of gratitude and appreciation.