Dave Chappelle shuts down House of Blues with brilliant marathon set

Dave Chappelle has been popping up for last-minute shows across the country lately like a comedy Whac-a-Mole, and Chicago got its chance to play last night when the standup performed two sold-out sets at the House of Blues fueled by improvisation and audience interaction.

Chappelle took the stage for the late set at 1:15am Monday morning and only ended at 3:50am after House of Blues management told him they were shutting down the club.

What took place in the two and a half hours in between was a virtuoso display of freestyle riffing that started with Chappelle telling the audience that he had nothing new to say. But in truth, this was a brilliant comedic mind unleashing itself.

 Chappelle is in seeking mode, trying to figure out exactly what he wants to do with his life creatively after he walked away from a big "Chappelle's Show" payday in 2006. Maybe movies will fuel his comeback, he suggested at one point. However he returns to show business full time, he added, this time he aims to sell out as hard as possible, right down to plastering his face on paper plates and stripper pasties.

One of his most inventive riffs on maintaining creative integrity vs. selling out included multiple ad spots for Dave Chappelle alligator shoes, with endorsements voiced by none other than Barack Obama, Nelson Mandela and Billy Dee Williams.

The politics of race in America is, of course, Chappelle's great subject and he zeroed in on that aspect of Chicago right away, noting there's something strange about our city. "You can't see the racism," he said, "but you can smell it." (He also said of the city, "Chicago has antique weed. It's all full of stems and seeds and shit.")

His brilliant stream-of-consciousness set started off raunchy, with a riff on a post-fight interview with a KO'd vagina spurred by a line from rapper 50 Cent about how he "beat that pussy up." It was one of several riffs along those lines that kept popping up throughout the set (another played with the chorus of Tyga's "Rack City").

In the opening salvo of what became a weird, wild and ultimately wonderful dialogue with the audience, Chappelle asked an audience member in the front row if he was Middle Eastern or Mexican. "Either way, I'm going to call Homeland Security just to be on the safe side," he said, before thanking Americans of Middle Eastern and Mexican descent for taking over the nation's racial hot seat and giving African Americans "a well-deserved break." (This lacerating bit was made all the more challenging by the sikh temple shooting near Milwaukee.)

There were far too many inspired bits to keep track of. The set jumped from Chappelle musing on the underwater burial of Osama bin Laden ("too much room for a sequel," he said before going into an underwater broadcast as the undead terrorist, adding, "It's Aquaman's jurisdiction now") to saying the "bath salts" craze was so bizarre he hadn't written any jokes about it ("You guys don't need my help with this one") only to suggest paying a member of the audience to take some bath salts and watch to see what happens. He called the idea "Comedy Myth Busters," as well as the most irresponsible idea in entertainment history before doing a newscaster riff on what kind if trouble such a stunt would get him into.

There's just too much to delve into here. As soon as I recall one of the creative pathways Chappelle took his comedy careening down, six others pop into mind. Like the bit about watching "Hotel Rwanda" and getting into a conflict with a theater usher sick on bad shrimp. Or how he time-traveled into the early 90s to see a concert he thought he missed only to spot his younger self there and engage him in both conversation and sexual hijinks.

Aside from a brief musical interlude by a band fronted by French harmonica player Frederic Yonnet (and a guest spot by rapper Talib Kweli), it was all Chappelle, chainsmoking into the wee hours and gamely fielding all manner of bizarre questions and setups from the audience.

In 2004, Chappelle blew up at a California audience after hecklers requested his Rick James impression. The comedian spoke of how he had always considered his audiences intelligent, but that, in reality, "You people are stupid."

During the late-night Chicago show, an audience member yelled for Chappelle to do Rick James. But many in the crowd booed the man and a guy in the front row said the comic should only do material he was confortable performing.

Chappelle warmly saluted the fan in the front row and marveled that, unlike the way this scenario usually plays out, in this case a black audience member demanded the impression and a white audience member defended his artistic integrity. Rather than ending the set, Chappelle kept right on going. He might be onstage still if club management had let him. (Back in 2007, Chappelle performed a six-hour set.)

As he finally threw in the towel, Chappelle addressed the Chicago audience, seeming to do a callbackto his 2004 tirade. "I was wrong," he said. "You're smarter than me."

Not by a longshot, but most in the crowd seemed to leave feeling pretty smart for buying a ticket to one of the most remarkable standup sets they'll ever see.

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Laura Baginski, Editor (@TimeOutChicago)