Dierks Bentley held court at Nashville’s Bridgestone Arena on Saturday (Sept. 7), calling the 20,000-seat venue “the biggest honky tonk on Lower Broadway.” He should know, he’s played many of Nashville’s tiny clubs early in his career, perhaps most notably the iconic bluegrass room The Station Inn, cultivating his mix of country, rock and bluegrass-tinged music, before breaking through with his 2003 debut single “What Was I Thinkin’.”

His comparison with Lower Broadway’s ever-growing slate of honky-tonks (including his own Whiskey Row, which opened in 2018) was apt, as the evening was filled with many of the hallmarks of any number of club-sized venues dotting downtown Nashville, including guest artists dropping by, ’90s cover songs aplenty and even some karaoke moments.

Two decades into his career, Bentley has earned 18 Billboard Country Airplay No. 1s and 15 Grammy nominations. Veering along country music’s sonic sweep of sounds, encompassing rock, ’90s and 2000s country and rock, and bluegrass, Bentley offered hits including “I Hold On,” “A Lot of Leavin’ Left to Do,” “5150,” “What Was I Thinkin’,” “Black” and “Livin’.”

“My hope for the show is that you find a moment where you feel like you’re living,” Bentley told the crowd.

He’s also forged a concert style that blends hits, a genuine onstage ebullience that easily outpaces many of today’s newcomers, and intentional audience engagement (such as bringing one fan onstage for a beer-chugging challenge and offering another fan a karaoke moment). Bentley’s crack band — including Charlie Worsham, Ben Helson, Tim Sergent, Steve Misamore, and Cassady Feasby — provide a perfect foil for Bentley, not only musically, but they easily match his often goofball humor, such as their humorous, hockey-themed band intro video and when Bentley repeatedly jumped in front of bandmate Worsham during Worsham’s take on Garth Brooks’ “Callin’ Baton Rouge.”

The wide range of music in Bentley’s show — gobs of ’90s country covers, Bentley’s own two decades of 2000s hits and music from many of today’s buzziest newcomers — chronicled the evolution of country music’s soundscape.

Opening for Bentley was bluegrass/Americana newcomer Bella White, who offered up songs from her album Among Other Things, including songs about fizzled relationships (“Break My Heart”) and dirtbag men (“Marilyn”), as well as a sterling version of Lucinda Williams’ “Concrete and Barbed Wire,” which drew devoted applause from the concert’s early arrivals.

Meanwhile, fellow opener Chase Rice offered up a set filled with personal meaning for the singer-songwriter. The acoustic guitar he played was one his father had given him when Rice first started learning music. Noting that his father died two years after he was given the guitar, he honored his father’s memory by performing one of the first songs he played for his dad, John Denver’s “Take Me Home, Country Roads.”

Rice was first known as a songwriter, contributing to the Florida Georgia Line’s “Cruise” before he notched his own pop-country hits, including “Ready Set Roll” and “Eyes on You.” He included all of those in his Bridgestone set, but best highlighting his talents were his newer songs, such as “Haw River,” that will be on his new album Goin’ Down Singin’ (out Sept. 20), showcasing his more roots-leaning, rawer sound and matured songwriting.

In his own set, Bentley welcomed The Red Clay Strays lead singer Brandon Coleman, as well as country singer-songwriter Zach Top.

Here, we look at the five top moments from Bentley’s Nashville concert on Sept. 7.