Entertaining Complaining: Kyle Kinane’s “Loose in Chicago”

The Windy City–bred, LA-based comedian takes on the joys of concealed carry and Laotian honeymoons in his new Comedy Central special.

Staying loose in Chicago wasn’t just a lifestyle for comedian Kyle Kinane growing up—it was a survival instinct.

“The Midwest has a sense of, ‘Listen, things are probably gonna suck… But now that you know that, have a good time,’” he explains. “It’s not, ‘No worries.’ It’s, ‘There are worries, but we all have them.’ If you’re not gonna laugh, you’re gonna cry about it, so you might as well laugh.”

Take George Carlin’s enthusiastic, raspy growl down a couple octaves and direct half of those trademark observations on society toward cutting, self-deprecating introspection, and you get Kinane’s distinctive stage presence. Kinane’s gruff beard and lively storytelling call to mind a hard-living seafarer who just docked and can’t wait to tell you the insane shit he’s navigated.

“If you’re gonna complain about something, make it entertaining,” he says. “Otherwise, nobody cares. Growing up, I had friends who were so funny, if you heard somebody had a bad day, you were excited! Because it was gonna be the funniest thing you’ve heard all week. It was like the freestyle rap of my group of nerdy white dudes. We were all dorks and losers, but we developed an advanced sense of humor very quick, because that was our only form of defense.”

Between keeping up with his smart-alecky childhood friends and staying up with his mom to watch Johnny Carson’s Tonight Show, Kinane’s sense of humor advanced quickly. He grew especially inspired by Mitch Hedberg, whose grinning self-awareness shifted the cultural appearance of stand-up comedy drastically. “Mitch Hedberg looked like somebody I would hang out with—not somebody in a sport coat who looks like a friend’s dad,” Kinane explains. “Like a regular guy who wandered into this and had some self-doubt on stage [and] doesn’t even know if he should be here… That’s how I feel about it.”

“I wanna be the voice of the Puppy Bowl. I’ve thrown up on Drunk History enough.”

“Here” can mean a lot of different places for Kinane these days. He moved to LA years ago to perfect his stand-up (“It’s so much easier to be miserable in California,” he admits), which has recently led to the strange new world of acting gigs. As Eric, a loser ex, on Netflix’s dramedy Love, for example, he had to translate his brutally honest act into onscreen vulnerability. “I always feel like an imposter when I’m on a set,” he says. “It’s hard to tell if your own work is good. At least with stand-up, you get an immediate response. But acting, all you hear is ‘Cut.’ And you’re like, ‘Are we cutting because you know I’m not gonna do it any better?’” he laughs.

All modesty aside, Kinane’s schedule—which includes the second season of truTV’s Those Who Can’t—fits a Midwestern work ethic, and a high demand for his gruff voice keeps him busy; he’s working on Disney XD’s animated Right Now Kapow while continuing his tenure as Comedy Central’s go-to voice-over artist. Still, he’s yet to achieve his dream role: “I wanna be the voice of the Puppy Bowl,” he says. “I’ve thrown up on Drunk History enough. Let me branch out into the world of kittens and puppies!”

But first things first. Barfing in period dress notwithstanding, stand-up has always been Kinane’s number-one priority, and his newest hour-long special, Loose in Chicago, premieres on Comedy Central at midnight on October 15. After years of tales about excesses, misbehaviors, and insane encounters, Loose in Chicago captures some recent adult-world consequences he’s confronted—including awkward physicals and a gout diagnosis—all with his signature delivery as the guy at the bar who you want to complain a little too loudly.

Fitting for a show performed in his hometown (at Metro, a short walk from Wrigley Field, Chicago’s longtime monument to real-life frustrations—though that may be changing soon), Loose acts as a loop of theater and therapy. “Everything that happens to me gets processed through comedy. Whether or not I even say it on stage, that’s my default,” he explains. “Aging, finding out health issues… It’s all gonna be fine if I can get a decent joke out of it.”

Crafted through hard work and received by hysterical audiences, Kinane’s jokes rank far better than “decent”—especially when they get indecent. FL

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