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The organizers of the Comedy Exposition—the new stand-up festival in town—explained to me that hosts can be some of the trickiest roles to fill. Keeping the flow between sets is not only dependent on a host's comedic finesse and ability to think on the fly, but also his likability. Luckily, Lebovitz is a naturally likable comic. Though slightly disheveled and always just a touch wild-eyed on stage, he never comes off as a blowhard, like he wants you to know he's working hard for the joke. Part of his charm is that he seems like an entirely relatable Chicagoan (he was raised in Hyde Park, after all), the dude at the bar's Algonquin Round Table with all the best jokes and all the best digs. And now that charm will forever be captured on a compact disc.
This weekend Lebovitz is recording his poetically titled debut, Pure Garbage (Stand-Up! Records), over the span of three shows at Timothy O'Toole's, the venue at which the stellar stand-up collective Comedians You Should Know—of which Lebovitz is a part—has a weekly showcase. "I have the rare opportunity to do a whole hour at the venue in which I developed a lot of the material," Lebovitz tells me. "People have seen this stuff in the process, but never seen it polished." He's planning three slightly different sets to, you know, keep things spontaneous, and when I spoke with him yesterday on the phone he seemed strangely at peace. "It's like when you cram for a test and stay up all night studying," he explains. "The test is at 10 AM but when it gets to be 8:30 AM, you kind of just chill out and eat your breakfast."
Part of the show's hook is that Lebovitz may not be much longer for Chicago. There's talk of an upcoming move to New York City, though he admits the dates still need to get hammered out (and that he enjoys telling good lies to generate buzz). Still, we should probably enjoy the comic while we still have him. When asked about his impetus for an NYC relocation, Lebovitz sees it as almost a necessary measure to stay grounded and, in turn, grow as a comic. "I remember when I first came up. Hannibal Buress, Kumail Nanjiani, TJ Miller, Nick Vaterott were around. And while I'm still super inspired by my peers here, some of those people on the top rung have become my peers. I want to be in a place where I might get bumped for Louis CK. That'll be good." So I guess we'll just have to lobby for Louis CK to show up to the album recording.
Mike Lebovitz, 10/24-10/25: Fri 9 PM, Sat 8 and 10:30 PM, Timothy O'Toole's, 622 N. Fairbanks, 312-642-0700, comediansyoushouldknow.com, $15, $10 in advance.