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Remember When Dierks Bentley Played Lollapalooza?

Dierks Bentley
Jeff Getner, Getty Images

Eric Church and the Court Yard Hounds are far from the first country stars to step out of their comfort zones and play the ultimate rock-fest known as Lollapalooza. Five years ago yesterday (Aug. 2), Dierks Bentley took the stage at Grant Park in Chicago, attempting to win over a skeptical crowd.

Reviews from country music outlets like CMT praised Bentley’s set. He proved he had a rocker’s spirit, but never deviated from his pure country setlist. A Waylon Jennings song opened the show and a Johnny Cash song closed it. In between, it was his personal hits like ‘Free and Easy (Down the Road I Go)’ and ‘What Was I Thinking.’

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.

Next: Remember When Charley Pride Played Professional Baseball >>

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