Kyle Kinane: ‘Being uncomfortable is like job security’

If you like your comedy soaked in sarcasm and drowned in whiskey, Kyle Kinane is a guy you are going to need to see. His narrative-based material leads the audience through a maze of logical observations as he navigates some of the most ridiculous memories of an already-absurd life. Kinane has released two critically-acclaimed albums, Whiskey Icarus and I Like His Old Stuff Better, both of which were filmed for Comedy Central. And currently, he’s putting the finishing touches on material for his next album. To call him brilliant seems like a disservice through the oversell, but let’s just leave it at this: He’s incredibly intelligent, a little cynical and wickedly funny.

LEO: This time you’re going to be playing Haymarket Whiskey Bar. Are you a bourbon fan?

Kyle Kinane: Yeah. Last time, I was at The Bard’s Town, and when they moved it to a whiskey bar I was like: ‘Yeah, that sounds about right.’ I’m not trying to go down in history as the world’s biggest booze bag … but yeah, who doesn’t like a nice sipping-bourbon?

LEO: Did you always want to be a comedian?

KK: Do you remember career day in school? ‘What do you want to be when you grow up?’ I didn’t take to anything, but I remember watching Johnny Carson and thinking: ‘He just stands there and talks: How do I get to do that? I’m not good at sports. I’m not super smart or interested in stuff, but that guy just stands there and talks, and people laugh at him. I could do that job.’

LEO: What was your first time on stage like?

KK: Unofficially, I guess I did it in my school talent show in fifth grade. It was like, let’s put this stand-around-and-talking thing to the test. It turns out that was fun, and it went really well by fifth-grade standards. And then I took a hiatus for about 10 years and started back when I was 22 in Chicago. I didn’t have much going on ... This was something I had been talking about my whole life, so I tried it out.

LEO: Was there a specific moment when you knew the comedian thing was going to work out?

KK: I still don’t know how long this lasts. Just two nights ago, just playing around town practicing, I had two bad shows in a row — and I was like: Well, maybe that’s it. Maybe you’re not funny anymore. You can’t get comfortable, as soon as you’re comfortable, you’re screwed.

LEO: Do you think you’ll ever get comfortable?

KK: Being uncomfortable is like job security, because you always have to worry about it. It means you care about it, and we want to constantly get better. It’s what ensures that you stay relevant.

LEO: In your opinion is a joke ever finished?

KK: Not to me. You can always retool it, or rework it somehow and make it better. It’s like a model train set. Guys don’t build model train sets because they want to someday see it finished. They build model trains because they like sitting there putting little trees down or redesigning the track. A joke is like that — there is no end to it. It’s great.

LEO: Much of your material is story-oriented, from personal experience. How much is truth, and how much is exaggeration?

KK: How much do you want it to be? Is there going to be someone in a bar that goes, ‘Wait a minute, I can’t laugh unless it’s 100-percent truthful?’ It’s not a court case. It’s all rooted in what I remember is truth, and then some people laugh at certain points more than others, so those parts get a little more attention to detail.