Shucking the day job and hitting the open road is a dream for many, but for aspiring comedians, it’s a mandatory step to full-time success alongside countless open mics, late gigs at half-empty clubs, and competing with loud drunks and bar televisions all to hone their craft and launch their name. For The Cherokee Effect Comedians, we interviewed four performers who made the journey from 9-5er to professional comedian to learn how they did it and how today’s aspiring comedians can too.
First up is Kyle Kinane, a Chicago-based standup who has appeared on Last Call with Carson Daly, Comedy Central Presents, Conan, Drunk History, and more, not to mention two albums (Death at the Party, Whiskey Icarus) and a gig as the voice of Comedy Central since 2011.
Where were you in life when you first tried comedy?
It was ’99, I was between my second or third college and was working at a gas station and delivering pizzas. I was still making an effort to go to school then.
Where did you first try it? Were you hooked right away?
Well the first time I tried, I just read this thing in the newspaper that was an open call for standup comedians. I had never even gone to see standup – I’d seen it on TV, but I didn’t know where you go see it live. It was an open casting call the same day in Chicago, you just go down there and do two minutes, and I was like “Ah, why not?” So I went down and there were a bunch of people there, and I wasn’t exactly hooked – it was more like “Well, I got that out of my system.” It was this weird casting call in the middle of the day. I remember doing my two minutes and not really getting a sense of what was going on. It wasn’t a really good representation of what comedy is. But then like a year later I was going to Columbia in Chicago and I saw a guy who I’d seen at that [casting call] and I said “Hey you did that comedy thing. How does that work?” He told me about open mics – I didn’t know what open mics were. I started going and watching them to see what people were doing, not in a pressure situation but just trying things out. I watched for a few months before I even had the balls to try it.
Was there a point where you made the decision to pursue standup as a career?
Nah. I kind of resigned myself to the fact that I was going to make money doing whatever kind of crap during the day. I didn’t have much of a career focus in my life – I just wanted to have fun and have an outlet for things, and that’s what music was earlier on, then comedy came in and sort of streamlined all that. So I figured it could be a great outlet, and once I tried it, it was this new puzzle to figure out.
When you started doing standup regularly, did you find it hard to balance it with your day jobs?
No, because I live my life – I mean I guess it’s kind of lazy – but I live my life to maximize the most fun out of it. I’ve always worked jobs that don’t take my mind away from me. I’ve always just worked however many jobs I needed to let my pursuits remain untainted, whether that be comedy or music. I’ll do the crappy job that makes me physically tired, but mentally, it can't wear me out to the point where I don’t want to write jokes.
So you’re pretty indifferent about working a 9-5 job.
Yeah, I’d probably still be somebody working at a gas station if comedy hadn’t gone anywhere. The last job I had was doing closed captioning for television. But yeah, nothing that required many qualifications. I would’ve probably been on the lower end of the pay scale for the rest of my life – and happy. That’s the thing; I’d do comedy for free just because I wanted it to be this pure thing. I didn’t want to try and make a living off comedy but then have to change my act or deal with babysitting drunks.
So you’ve never looked at “going full-time” as a specific goal?
That’s my version of quality control – if people want me to do standup I’ll find out, but I’m not going to force myself onto the world. When people just start they’re like “Oh, there’s no way I’m working a day job” then make fifty bucks hosting an awful comedy gig – I didn’t.
But isn't there still a certain amount of effort you had to put into it?
Yeah, I mean I have an agent and stuff like that. And you can always look back on those one-nighters and terrible gigs nostalgically, but it’s always looked to me like you are whoring out something you like, you know? Like “Oh I love comedy! I’m just gonna sell it for minimal amounts of money for people who don’t care about what I’m doing!” Ugh…I don’t want to do that. And when it comes to delivering pizza to people and working at a gas station and meeting weirdoes in the middle of the night – I like those jobs. The last place I worked at was great. I had health insurance and made a passable living – minimum wage, but I paid my bills. But those jobs where you get to meet weirdoes – I enjoyed doing those things.
So you miss those jobs?
Oh I mean, there’s a new fear, like it still feels silly that comedy is a job. So there’s a new type of terror of “Am I going to have to go back to a job? Am I going to have to go back to the working world?” Because I don’t have the skill sets put into place. I hear about people getting laid off and they’re 50 and they’ve got to find a job and they never were salesmen, stuff like that…and I wonder if you can get laid off in comedy. Who knows? But yeah, I miss it. I miss sitting around a pizza place getting stoned with my friends and laughing at everything all the time, but you start looking like a loser if you do that for too long in one place.
What’s your take on the idea of “paying your dues” in comedy?
There’s this impression that paying your dues is working the road and doing all these shitty gigs. I think that’s one avenue, but there’s not just one way to do it. Some people pay their dues by getting up and going to a horrible job every day, then when they get off they go out at night. Maybe they have a wife and a kid or a girlfriend, so they’re sacrificing time in that relationship to go out and pursue comedy. I never had that, I kind of streamlined things on purpose. That’s another thing too – working that soul-crushing job all day then at night, when all you want to do is kick back because you just worked, going out to that grind and performing comedy for free. That’s its own way of paying dues, in my opinion. It isn’t better or worse than starting on the road with all these horrible gigs in the middle of nowhere.
Are there certain mistakes you see aspiring full-time comedians make?
I think people move away from their paths too early. I’m sure I could’ve benefitted from a couple more years in Chicago before I moved to LA, but it’s only hindsight. Everybody’s just itching to get out, and it’s only in hindsight you realize you should’ve stayed a little longer. I was fortunate by starting in Chicago and growing up there – that was a good scene where people pushed each other, but a lot of people just make the move from nowhere to New York or LA instead of trying to go to a secondary city like Denver or Chicago or some place to learn, get around a lot of likeminded people, get inspired by your peers, and get excited without the pressure of an expectant city that crushes you.
What’s your advice for comedians who want to go full-time?
If you want to be a comedian, do you love it enough to do it for free indefinitely? That was my thing. I’m willing to do it for free, forever. I quit a day job four years ago, and I’m still terrified – and I did it for ten years for free. Are you willing to do it for free forever, but also do it seriously – take it past the idea of it being a hobby? If you can answer that question with a yes and the talent and work ethic are there, you’ll make it. That’s my best guess. Some people get accolades early on and they get comfortable and forget that people who work harder are going to pass you more often than not.
And when people think of it as a career – that’s the first mistake, I think. Don’t think of it as a “career.” You’re lucky if you ever get there – I’m the most fortunate person in the world because I turned my passion into some semblance of employment, but I never got into it thinking “Oh you know what? I’m going to turn this into a career!” That’s a silly way to think.
It sounds like you’re not much of an overthinker.
Well, why would you think that the world needs another comedian, you know? To think there’s enough money in the world to pay another comedian to tell jokes? That’s why I’m just holding onto this very tightly. [laughs] Just the idea that “Oh, you tell jokes? Here’s your money” — what?! That doesn’t sound right. So if you do make it, be ever respectful of the fact that the universe lets you tell jokes for a living. Never forget that that’s your job.
Photo credit: Cassie Wright