When Addison native Kyle Kinane decided he wanted to do comedy as a student at Columbia College, one major problem stood in the way. “I didn't know where, how you started comedy,” he told RedEye. “You were either funny at a bar or you were a guy on TV telling jokes.”

Now, after years of being in bars, Kinane has told enough jokes on TV on Comedy Central, “Conan” and elsewhere to feel secure quitting his day job. He chatted from his LA home about his time in Chicago, his interest in extreme sports, and, well, hanging out in bars.

A lot of your bits are about this sense of failure and sitting at your job at feeling depressed, but now you're becoming successful. Is that changing the kind of stuff you're working on at all?

There are always new ways to fail, I guess.
There are! There are always new ways to fail.

But you were working a day job until pretty recently, right?
Yeah, I always had, I think, a healthy fear of being broke. I mean, I was always broke, but at least with a day job I always knew exactly how little money I was going to make each week and could plan accordingly. Whereas with comedy the big fear was you maybe make a decent amount this week but then for three weeks you don't. It's feast or famine. It's kind of like working like a freelancer in that sense, and that's terrifying.

What were you doing right before you quit?
That, I was working in an office closed captioning television. That was a particularly insulting job. I mean, the job itself wasn't bad – you just sat there and watched TV all day. But to be in LA surrounded by people hoping to write their own TV show and being forced to type out somebody else's TV show –  which is ultimately, of course, much worse than [your friends'] idea.

What about when you were in Chicago? What kind of jobs were you doing?
Oh man, Chicago. I was delivering pizzas and driving forklifts. A lot of menial tasks. My whole approach was “I'll beat myself up physically, but don't give me anything mentally stressful. Let me listen to music, let me write jokes while I work.” That was always my requirement: “You can have my body, but don't take my mind. Don't make me concentrate on something.”

What was it that prompted you to move from Chicago?
I mean, you get to a point where it's like you can start working the road from Chicago, without any TV credits or anything. You're just doing the one-nighters and outlying bars and hoping to advance through the ranks there. Or you put all your eggs in one basket and move to New York or LA and then hope to get your stuff seen in town and then get a TV credit and then go out on the road, which obviously that's the route I took. I think they're both great places. And, you know, there's the weather. I know it's a cliché, but it's true. I like New York, but it seems like you never get to be alone. Even when you're in your house you still have five roommates because of how expensive it is.

Just based on the tenor of your act, did you have any particularly defeating experiences in Chicago where you were like, “I'm fed up and I really want to get out of here”?
No, I mean, I was never fed up with the city, so to speak. My whole thing was that I lived at home. I lived with my folks, so I was moving out of my folks' house, and I was like “Well, I'm either going to move 20 miles east and move into the city and spend all my disposable income on rent and everything just to live a half-hour closer and do what I was doing anyway. Or I could just pick up and leave.” So that's what I went for.

How did you get started with comedy originally here in Chicago?
I had always been playing in bands, and maybe it was like an attention thing. I realize looking back I was – I probably still am – incredibly obnoxious, but I like to think I've mellowed out a little bit.

What kind of bands were you in?
Like punk bands...we played just Chicagoland and 'burbs. We played at Thurston's once in a while when that was still in existence. But yeah, it was just me doing it to make something. I didn't really have a career idea that I was pouring myself into – I had to always have something to put creative energy into. Whether it was playing music, and then that kind of ended. And I was going to Columbia for writing, and the only time I really enjoyed class was when you get to read your papers out loud and people would laugh at the jokes that I put in there. I was like “Why don't I just tell these jokes instead of writing them down and waiting a week to see if someone thinks it's funny?”

What kind of papers were you writing that you were putting jokes in them and reading them out loud?
Well, it was fiction-writing class. Or creative nonfiction. So it was just stories that when everybody – especially college, everyone's so melodramatic – I really got turned off by the idea that every writer in my classes, most of them felt that everything needed to be this epic, touching story or some kind of tragic event. It was like “Nah, it can still be hilarious,” you know?

Okay, so you were writing jokes –
[LOUD CRASHING SOUND] Sorry, that's just some nerds on their motorcycles – nowadays motorcycle guys are nerds. It's like “look at you dorks with all your little accessories.”

So obnoxious!
Yeah, and the mopeds picked up a lot of steam. It's like “Yeah, you know what I want? I want a bicycle but I want it to break down every other day. Oh! A moped!” Too tough to ride a bike and too much of a [bleep] to get a motorcycle.

Is that a big thing in LA? Are there a lot of mopeds?
Yeah, but then you hit one hill, and it's like “I quit.” I don't know. I really have nothing against them. I like bicycles myself.

I read you got really into mountain biking, actually.
Yeah, I crash that all the time. Been doing that for the past few years and just falling down. It's mostly just crashing. Not too much riding. Mostly crashing. I'm trying to get these things out – stuff I never did in my 20s. I just drank and got stoned. I mean, I was doing comedy, but I stopped skateboarding and bike riding. And now it's my mid-30s. I'm like “I'm just going to be totally old and not be able to do any of this anymore. I've got to do all this fun stuff that I missed out on in my 20s.” So I'm biking, I tried to learn how to surf, got a skateboard. Like, I'm bad at all of it, but I'm still doing it while my body's going to let me...It's also just one of those real, like, mature [realizations], like, “I'm not bouncing back from things like I used to. I can stay injured now.” I threw my back out, also. It's like, I better take advantage of being semi-young while I still can.

It's kind of like with hangovers as you get older. You can't just drink a lot and bounce back. It's kind of a crushing realization.
That, and the fact that drinking a lot doesn't lead to the craziness it used to. It's like, “Oh sure, I got drunk, but that was it. I had a reasonably insightful conversation with friends, I guess, and then I went home.” It's sadly predictable. Not to say I don't do it anymore, but the big question mark of “What crazy thing's going to happen tonight?!” isn't really there.

So you went from writing jokes in your class to performing around Chicago?
Yeah, I had gone out for one – I saw something in the newspaper – sort of open cattle call for some festival at Zanies. A hundred guys doing three minutes. So I signed up for that. I didn't know where, how you started comedy. You were either funny at a bar or you were a guy on TV telling jokes. I didn't know where the middle ground was or how you started in that. And so I did that [at Zanies] and was like “Alright, got it out of my system.” I didn't really meet anybody there, but then a guy in one of my classes at Columbia, I recognized him, and I asked “Oh, do you do comedy?” And he told me about all these open mics, and that's how I started doing open mics.

It seems like because of all the improv and sketch, people aren't as aware of the stand-up scene here in Chicago.
Well, now standup's kind of a hip thing to do. It's not this [thing], like, I'm scared to tell my friends that I tell jokes. Like, I tell a couple band guys that I'm going to tell jokes and they're like “You try to make people laugh on purpose? That sounds stupid.” And now, now nobody cares if you're in a band but it's interesting if you do standup.

It seems like there's also a new idea of what a standup is with Twitter, where people can be comedians in the sense of just writing jokes online. Do you think Twitter has changed what it's like to do comedy at all?
There's a lot of people that perform standup because they want to be comedy writers. And where do you showcase your jokes if you're a writer? Well, you have to perform them live and make people laugh at them. You might be terrified up there, but if the joke's well-written, it'll get a laugh and you'll know “OK, what I'm writing is good.” Now Twitter allows you to do that without the live aspect. So to call someone a comedian just because they have a funny Twitter account? I don't know. I'd call them a funny writer.