Dierks Bentley has historically kept a heavy touring schedule, but he's got one date on this year's calendar that seems just a bit out of place. He's set to play Lollapalooza, a concert weighted toward hard-rock acts, in Chicago in August.

The concert's lineup includes Radiohead, Nine Inch Nails, Rage Against The Machine and rapper Kanye West, atypical of the names that usually surround Dierks in festival rosters. But it's not without precedent. Dierks walked into a similarly odd situation last summer when he played the Bonnaroo Music Festival in Tennessee, alongside the Police, Widespread Panic, the White Stripes and Tool.

"Honestly, we didn't know if anyone would even show up to see our set," Dierks says, recalling Bonnaroo. "But we were pleasantly surprised to have a huge crowd who were genuinely into the music. When the Lollapalooza offer came in, it seemed like another opportunity to go out as the underdog and try to win over some new fans."

The Lollapalooza date takes place at Grant Park, the same location in which Shania Twain shot her 2003 TV special UP! Live In Chicago.