How can you tell a good comedian from a great one? A simple litmus test is to see how they respond when they’ve finally hit their groove, creatively and commercially. When their material and reputation is good enough that they can start selling out theaters and clubs on name recognition alone.
Watch what they do next. The good ones stay the course, giving you variations on the same kind of jokes and anecdotes that helped push their careers ahead. The great ones start getting playful, experimenting with the form and daring themselves to try new things and new ways of getting people to laugh.
By that simple metric, it’s obvious that Kyle Kinane is well on his way to greatness. He’s already one of the better joke tellers around, turning the conversational style of comedy into an artform. He’s the guy at the bar or at the party that you keep plying with drinks so he’ll keep telling stories. But on his latest stand-up special Loose In Chicago, it becomes clear how Kinane is trying to stretch himself and his material.
The most obvious signpost is his willingness to delve into the murky waters of political comedy. And the smartest choice he made was by not diving in headfirst. He wades into the conversation subtly while staying true to his particular voice. He deftly pivots from his ridiculous patriotism regarding mass murder during a Jack the Ripper tour in London to a discussion of gun control in the U.S., wondering aloud if anyone would really be upset by the Westboro Baptist Church folks getting gunned down en masse.
That opens him up to talk about how he somehow admires the WBC for bringing disparate groups together to protest their hatred of Rev. Fred Phelps and co. like, in his example, the LGBT community and Hell’s Angels. Here he pulls us back into his singular point of view by imagining a burly biker conversing with a gay protester: “What’s that? ‘Cute vest’? Oh, thanks, thanks. Like yours too. I wouldn’t have done all the fringe but I like what you’re doing.”
The rest of the special sits well within Kinane’s comfort zone of self-awareness, drawing in the stranger moments from his life and his own absurdist way of thinking. This all coalesces in a brilliant extended riff on the fact that he has been diagnosed with gout. From that nucleus, he spins out long yarns about his overinflated ego, his terrible conspiracy theories, and how his doctor smoothly worked a testicular exam in with their heated discussion about sandwiches.
Not to get too high minded about it, but this special felt like jazz. Kinane set the foundation and then peeled off from it into these extended solos that felt like improvisation but have been honed and perfected after months of shows. His comfort with the material and his ability to extemporize with it is even better exemplified by watching his recent set on Conan. He was playing to a different audience and a much shorter timeframe, but he hit different beats with the same material and teased different laughs out of it.
Kinane is clearly reaching master status with his comedy, so now we have to wonder why more people aren’t clamoring to get a listen to it. This special and his previous one (I Liked His Old Stuff Better) were filmed in rock clubs (Chicago’s Metro and the 40 Watt Club in Athens, Georgia, respectively) and when he tours around the U.S., he’s playing in comedy clubs rather than grabbing choice spots at theaters or larger rooms. Perhaps it’s because he hasn’t written a funny/moving memoir and hasn’t seemed interested in developing a sitcom based on his life (though the thought of that has me giggling with joy). Whatever the reason, even as he’s gaining strength, the audience doesn’t seem to be growing with him. A special this good and this funny could very well be the tipping point. Best to get on the bandwagon now.
Robert Ham is a regular contributor to Paste and the author of Empire: The Unauthorized Untold Story, out now via Regan Arts. Follow him on Twitter.