Three decades ago, East Tennessee native Kenny Chesney was playing tiny dive bars that dotted Nashville’s downtown, such as the Music City dive bar The Turf, playing his songs for anyone who would listen.

He’s long since ascended to being one of country music’s steadiest hitmakers and stadium headliners, as well as a Country Music Hall of Fame member. But Friday night (Sept. 25), to celebrate the release of his 21st studio album, Silver Sands Marina, Chesney traded stadiums and massive screens for a pop-up show at the intimate, 4,500-capacity venue The Pinnacle, not far from those Broadway bars where he got his start.

Over the course of 22 songs, Chesney sailed through a mix of new songs such “Talkin’ Dirt” and the album’s title track, “Silver Sands Marina,” and drew from his deep well of hits on songs like “Reality,” “I Go Back” and “Living in Fast Forward.” He also offered up “something we haven’t done in years,” playing a hit from 2009 “Ain’t Back Yet,” which he last performed back in 2015.

Outside the venue, fans were already getting into the vibe of the album, thanks to the album-themed outdoor area of The Pinnacle. The area included the pink building featured on the album’s cover, as well as pier carnival games, food trucks, a limited-edition vinyl store and more. Fans who didn’t score tickets to the show also had the opportunity to hear the concert, as it was broadcast live on Chesney’s No Shoes Radio, on SiriusXM’s Channel 59.

Inside the venue, Chesney reflected on his early years in the music industry, telling the crowd, “When I first started in this business, I just wanted like one song on the radio so everybody back home would think I was cool where I could prove ‘em wrong or whatever it was..I thought, ‘If I could just get one song on the radio so me and my buddies could go around the country and play the places that our heroes  played, just one time… this past summer was our 34th trip, so it’s pretty cool.”

Energetic fans were packed into the upper balcony, as well as the floor in front of the main stage and surrounding a thrust stage. Ever mindful of his entire audience in the room, Chesney regularly made the rounds to every side of the room throughout the set, waving and smiling at the crowd.

He closed out the evening with “Just Don’t Happen Twice,” before waving to the crowd and signing shirts, hats and vinyl albums. Returning to center stage, he waved to the crowd and said “Thank you for celebrating with us. We’ll see you next summer!”

And indeed he will — Chesney’s 2027 tour will kick off his Original Vibe Room Tour, featuring Eric Church, Sheryl Crow and Greylan James, in April 2027.

Below, Billboard highlights five top moments from Chesney’s spirited and intimate show at The Pinnacle.

JAŸ-Z in 8 is four episodes in and has been insightful so far.

We covered the first three episodes after an exclusive screening a few weeks back on Sept. 13 — and on the red carpet, JAŸ-Z told Billboard that none of the conversations he had were “difficult,” even when he dug deeper into the some of the feelings he had when making some of his most emotional records.

Take a song like “You Must Love Me,” which he covered in the third episode for instance, when he rapped early on in his career about the guilt and shame he felt when he notoriously shot his brother in his shoulder, and the collateral damage he caused when dealing drugs. It’s always been a song that his core fanbase has revered — and he spoke on how the booth became therapeutic for an introvert such as himself. In there, he can say things that he would never say in a conversation with other people. That In My Lifetime, Vol. 1 track is one of his rawest songs to date.

I use that as an example to intro our takeaways from episode four because he and Rick Rubin start this one off with “Where Have You Been,” a song featuring Philadelphia rapper Beanie Sigel, where the two of them give one of the most heart-wrenching performances ever recorded on wax as they rap about the traumatic experience they had growing up without their fathers around. As Jay and Rick broke this song down, the Brooklyn MC revealed that he eventually made amends with his pops, only to lose him about a month later. It’s truly a sad set of circumstances, and gives insight into an artist who has been known for keeping certain feelings close his vest.

The rest of the episode took on a lighter note, though, as Jigga talked about his studio habits and process, the Best Rapper Alive convos people were having during his In My Lifetime, Vol. 1 era, and the now-iconic look of him wearing a bulletproof vest over a white t-shirt while wearing a Rolex.

Check out the four key takeaways we had from JAŸ-Z in 8‘s fourth episode below.