A 21st-century troubadour with an ear for classic country style, Dierks Bentley has blazed a searing trail through Nashville since his 2003 arrival. Born in Arizona in 1975, Bentley was a fan of Hank Williams Jr. and Waylon Jennings, and he made his way to Music Row after high school. There, he sat in on all-night bluegrass jam sessions and researched old TV performances for The Nashville Network while pursuing his country-music calling. Bentley’s love of honky-tonk 45s and savvy about modern audiences’ wants came together on his debut single “What Was I Thinkin’,” a whiskey-soaked romp through a wild night, and he went on to become one of Nashville’s hottest artists in the 2000s, releasing country-radio smashes like the breezy “Free and Easy (Down the Road I Go)” and the winking “Sideways” while headlining tours and supporting Kenny Chesney and Brad Paisley. In 2010, he saluted his love of bluegrass with the stripped-down Up on the Ridge, and over the rest of the decade he kept listeners on their toes with tracks like the simmering “Black” and the ruminative “Living” as well as the 2014 hit “Drunk on a Plane,” which turns a hard-luck tale about a non-refundable honeymoon into a high-flying anthem. Since 2020, he's also been counting down the most popular songs from Apple Music’s country charts on his show The Nashville Countdown. Bentley’s scholarship of country music and keen instincts have helped him flourish—and given the genre he loves modern-day strength.