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Dave Chappelle in Tinley Park for Oddball Comedy & Curiosity Festival

Dave Chappelle, via comedycentral.com

Before he began booking talent for the 15-stop Oddball Comedy & Curiosity Festival — which lands at the First Midwest Bank Amphitheatre Saturday August 31 (doors open at 5 p.m.), complete with a carnival-like sideshow on the concourse and handpicked local comics on a secondary stage — Geof Wills was for many years involved with a similar but far smaller event in the San Francisco Bay Area, consulted with his marketing partners at Funny or Die and put feelers out in the comedy community.

If he attempted to create a sort of Lollapalooza for comedy, the current president of Live Nation’s comedy arm wanted to know, would big-name acts be interested in joining his roster? Because he’d need big-name acts to put butts in seats.

As it turned out, they were — though it wasn’t always easy getting them to on board. Chappelle included.

“Any time you’re trying to put together something that’s, I suppose, big and different, then there’s toughness involved in convincing performers that it would be good for them and it’s going to work and stuff like that,” Wills says.

In the case of Chappelle, he adds, “I think maybe the timing is right.”

Surprisingly, though, the long-elusive Chappelle — more visible of late — wasn’t Wills’ toughest get. They’d known each other for many years (Wills has booked comedy shows for nearly a quarter-century, he says), which helped. So, presumably, did the company Chappelle would keep on tour: Al Madrigal, Jim Jefferies, John Mulaney, Kristen Schaal, Chris D’Elia, Demitri Martin, Chicago-bred Hannibal Buress, Flight of the Conchords, Jeffrey “Roastmaster General” Ross — all with loyal followings.

Do they all have Chappelle’s free reign? Probably not.

Says Wills, “Dave can do whatever he wants.”

Tickets $25 to $112.25 at www.livenation.com

Update 8-30-13: AP reports that Chappelle left the stage before performing his set at an Oddball stop in Connecticut Thursday. The apparent reason: heckling. As the audience booed, he reportedly told them, “I like some of you. I hate some of you. I forgive some of you but I don’t forgive all of you. You guys have totally ruined my chances for running for Congress or something. … Thank you. Good night.”

Read the whole story here.

Warning: strong language

[View the story “Dave Chapelle heckled at Oddball Fest” on Storify]