Dierks Bentley performs during Still Playing Possum: Music And Memories Of George Jones at Propst Arena in Von Braun Center on April 25, 2023 in Huntsville, Alabama.
David A. Smith/Getty Images

25 Dierks Bentley Songs That Prove He's a Musically-Innovative Superstar

Some of his newest material ranks among the best from his 20-plus year career.

Dierks Bentley is a rare breed. He's a chart-topping singer-songwriter who fills arenas, sure, but he also took the time to release an entire bluegrass album in the middle of his red-hot career.

You recognize his voice the moment you hear it. And while he may not be the one to land huge vocal runs or shred guitars, he's got an unmistakable style and a knack for writing some serious hits. Bentley manages to straddle that line between "light and fun" (with songs such as "Somewhere On a Beach," "Sideways," "Lot of Leavin' Left to Do," "Am I the Only One" and "What the Hell Did I Say") and bona fide country gold tear-jerkers ("Settle for a Slowdown," "Long Trip Alone," "My Last Name"). He's won over fans with his more-introspective hits ("Every Mile a Memory," "Riser") and steamier love songs ("Feel That Fire," "Pick Up," "Pretty Girls," "I Wanna Make You Close Your Eyes").

Despite collaborations with artists such as Jason Aldean, Cole Swindell and Blake Shelton, Bentley never really found himself dipping his toe into the bro-country waters. He's also collaborated with Miranda Lambert, Eric Church, Kenny Chesney, Patty Griffin, Maren Morris and more. Even Kacey Musgraves and Chris Stapleton sang uncredited backup vocals on his albums for fun.

In other words, Dierks Bentley really transcends any one trend in country music and instead presents the full mainstream Nashville country package. So let's dive into his 25 best songs.

Editor's Note: This story originally ran on Nov. 20, 2018. It was updated on Jan. 26, 2024. 

READ MORE: Dierks Bentley + Cassidy Black: Inside Their Sweet Love Story That Goes Back to Childhood