Dierks Bentley has always had a little bit of an edge to his music, but did you know that he once performed at Lollapalooza?

Bentley took the stage at Grant Park in Chicago on Aug. 2, 2008, attempting to win over a skeptical crowd that had assembled for what's traditionally one of the biggest rock festivals of the year.

Reviews from country music outlets including CMT praised Bentley's set. He proved he had a rocker's spirit, but never deviated from his pure country setlist. A cover of Waylon Jennings' “Lonesome On’ry and Mean” opened the show, and Bentley ended with a fiery cover of the Johnny Cash classic “Folsom Prison Blues." In between, he filled his hour-long set with early hits including "Free and Easy (Down the Road I Go)" and "What Was I Thinking."

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T-shirts with "Who in the Hell is Dierks Bentley?!" written on them peppered the audience, but Bentley didn't seem to take offense. Time Out Chicago reviewed his set, praising his band but criticizing his songs.

The singer's set came at 2:30PM on a hot Chicago afternoon. Even if he was "Lolla's token country performer," he did the genre proud that day.

Eric Church and Court Yard Hounds are also among the country performers who've performed at Lollapalooza over the years, and Kacey Musgraves is slated to appear in 2019.

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