“You’ve been in enough bars in Chicago that you’ve heard one guy being boisterous and all the friends laughing. That’s all it is. There’s no magic to comedy." | Kyle Kinane Credit: Callie Biggerstaff

It’s not restaurants, music, or even comedy that Kyle Kinane misses most: it’s the chatter of a crowded bar. “Eavesdropping is my entertainment,” the comedian says. “When I’d get off the road and be back in LA, I would go to whatever bar by myself just to eavesdrop and listen to somebody else tell a story to their friend. If somebody’s telling a funny story, they don’t care if someone is eavesdropping and laughing, that gives them more fuel to tell the story even more flamboyantly.”

Kinane’s newest stand-up special, Trampoline in a Ditch, out on July 24, is more than 90 minutes long, compiled from six hours of shows at Madison on State in Madison, Wisconsin. Kinane includes several routines with double-digit runtimes, like his story of being kicked out of Canada that stretches past 23 minutes of laughter. These jokes have ballooned through years onstage, the way a good story gets refined with each telling. “The more you tell a story, the longer it gets, the fish gets bigger, the thunder gets louder,” he says.

Kinane describes his mistakes, like a barbecue-dominant diet that led to a gout diagnosis, in detail onstage, but always with an undercurrent of hope that he’ll be slightly wiser in the future. Paired with his distinctive crackling voice, Kinane’s comedy feels like hearing a friend tell a story after several drinks. “You’ve been in enough bars in Chicago that you’ve heard one guy being boisterous and all the friends laughing. That’s all it is. There’s no magic to comedy,” he says. “Every bar in Chicago probably has three people in it better than 95 percent of the working comedians today.”

Kinane grew up in the western suburb of Addison, Illinois, and he starts his latest special with a joke about the midwest: “The part of the country that likes to remind you that there’s no shortcuts in life, and then in the same breath tell you how much the Powerball’s up to.”

That joke is one of a few illustrated in an animated short by Meister released in tandem with the album. In the animation, a sentient Powerball with a Kenny Dennis-esque mustache bellows Kinane’s material and pounds on a diner table as a TV blares “It’s free money, stupid” in the background. Like a music video in the early days of MTV, the short is a creative visual partner to Kinane’s voice, and an effective hook for the rest of the special.

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Kinane first performed music before comedy, navigating the DIY punk scenes in Chicago and the suburbs as a teenager pre-Internet. “The bands were all comedians already,” he says. While some bands mimicked the self-serious attitude of hardcore godfathers Fugazi, “the Meshuggenehs always made me laugh,” he says. “If he was struggling tuning his guitar, he would just be like, ‘I got your money already, I don’t care.’ And just play a whole set out of tune.”

Within a few years, Kinane started his comedy career using the open mike listings in the Chicago Reader. “Finding out who wouldn’t update their own listing,” he reminisces. “Driving from Addison to the city on a Monday night to find out that open mike hadn’t gone on for four years.” He performed his first stand-up set at age 22 at Lincoln Park’s Red Lion Pub in 1999 and continued going up at north-side venues like Monkey Bar, Lion’s Den, and Cherry Red.

Since moving to Los Angeles in 2003, Kinane has launched a podcast called Boogie Monster, described Chicago’s Haymarket Riots on Drunk History, appeared on Bob’s Burgers and Paradise PD, and narrated Comedy Central’s ads and interstitials. But he’s been most successful as a stand-up, releasing four hour-long specials along with a 30-minute segment on Netflix’s The Standups. Like a veteran band, he’s been consistently recording and touring new material for more than a decade.

And like many punk songs, Kinane’s material is not always easy to find again after the first time you hear it. The track names on his albums are never named after the jokes themselves, but they follow a wholly separate logic. For his first three albums, the track titles match Cheap Trick’s Dream Police, KISS’s Destroyer, and N.W.A.’s Straight Outta Compton, respectively, so you have to click play on “Detroit Rock City” to hear Kinane ask, “Anybody in here get so drunk last month you had to call a cab to take you to Wendy’s?”

The track titles began as a joke, but the comic has embraced them as a sign of a dedicated audience. “If these tracks all have real stupid names and people still find them, that means people are really looking for them,” he says.

Trampoline in a Ditch captures a Kinane who has changed for the better in his early 40s, even as his storytelling style has stayed consistent. He earnestly talks about finding stability in his relationship and drinking in moderation. “My earlier material was like, ‘Yeah, my life is not put together,’ and that resonated with people,” he explains, “and that’s the catch-22 of complaining about your life being in pieces: you get success because of how successfully you complained, and then you wanna keep your life together.”

“Everything’s going pretty good,” Kinane continues, “and I don’t want to be like, ‘Oh, I’m such a loser’ when I don’t feel that way about myself anymore.”

That honest self-examination also allows him to joke about current events as a cis white man without sounding like he’s stepped up on a soapbox or centering himself in someone else’s struggle. “That’s how I know I have white privilege, because I believe in ghosts,” he says on the track “Defender.” “That’s what you get to believe in when you don’t have any other problems to worry about.”

Despite increased scrutiny on comedians’ material, Kinane doesn’t consider any topic inherently off-limits for jokes, but he doesn’t revel in shock value or taboo for its own sake either. He writes with empathy from his own perspective as a guy trying to be better, personally and politically. “I don’t wanna be that guy, ‘Well you just can’t say anything on stage anymore,’” he says. “Yes you can! You just have to be good at how you say it. You can’t be a lazy comedian. I don’t respect lazy comedians.”

Still, it’s difficult to put the work in performing when the pandemic has shut down venues worldwide. Kinane has been working on new material while self-isolating with his girlfriend, alternating between their home in LA and housesitting in Oregon, “sitting around a fire pit drinking beer.” He has tried a few virtual performances, “but they do lack a little urgency when it’s just sitting in the garage looking at a computer,” he says. He misses the risk inherent in telling stories to the instant feedback of a crowded room. “A better wordsmith could probably come up with some analogy,” he says, “like some sort of tightrope walk over marshmallows.” v