The Steamroller: Just to get the boring background stuff out of the way first, you're from Pennsylvania originally? 

C.J. Toledano: I'm from Erie, PA.

TS: Really? I'm from Buffalo, which is only a few hours away.

CJT: Oh man… The second time I ever did standup was at Comix Cafe in Tonowanda [a suburb of Buffalo]. I didn't actually go inside the club, I did my set inside the lobby, in the bar area.

TS: They couldn't put you in the club?

CJT: No, I guess not. I drove up from Erie to do my second set ever and they put me in the bar. What happened was, I head about the place in a USA Today article called "Top 10 Places to See Standup Comedy!" It wasn't necessarily the best ten places to see standup, it was just ten places. "Do you want to be weirded out by standup? Go here!"

TS: About two years ago, you moved out to LA is to pursue an internship on Conan, what was that experience like?

CJT: I didn't really know what the show was gonna be, I got the internship before they even premiered the TBS show. The new show was a little bit different than the old Late Night, which I grew up loving. Everything was a lot shinier and bigger. But still, the things that I had really appreciated was the opportunity to watch the rehearsals and to get to hear from the writers what it's like to write for a daily show.

I met people I grew up watching, all these old Chicago people like Brian Stack, we would share these experiences that we'd had in Chicago comedy. We had these stories that were very similar, he spent time working with his friends back in Chicago and now they're all working in a professional environment together. It gives you an assurance, that if you keep working, you can all start making comedy for money... Somehow.

TS: It's always a gamble, meeting someone you've idolized like that, and it's so much more rewarding when they're down to earth.

CJT: Yeah, you meet someone in showbusiness who's sane, and it's like "oh, that's the goal. Not to be rich and famous."

It was just great being at Conan, while I was there interning, there'd be some down time and I'd write all these packets for TV shows. Being at Conan and writing my packet for Fallon was such a great reference point for my writing. That was probably the best tool I could have asked for at the time.

TS: You end up leaving Conan to write for Jimmy Fallon... You wrote and produced sketches featuring Fallon, Justin Beiber, and bunch of other folks, was that surreal, seeing jokes and sketches go from your head to the TV in such a short amount of time?

CJT: Yeah, that's the amazing thing about TV production… You start in comedy fucking around with a bunch of friends, saying stupid things to each other, and then eventually you're in an office environment, trying to sell these ideas to a head writer or to the host.

To see any joke you write make it to air is really satisfying, but you can't really enjoy it as much, because you're like "oh my god, I have to write something else immediately." When the show happens five times a week, you have to move on very quickly.

TS: Even with your background in sketch and jokewriting, through school and the Second City comedy studies program, was it still overwhelming once you're actually in it?

CJT: It's very overwhelming, and I still find writing overwhelming. The thing is, I feel like a lot of things are overwhelming, but writing is the one thing that I can complete and finish. Of any sort of work, I understand writing the most at this point.

TS: You've opened for Bo Burnham a handful of times this year, how did you end up working with him?

CJT: I'm still not sure how I ended up getting the gig. I was doing some comedy festivals last Spring, like the Bridgetown Comedy Festival, and somebody saw me. I guess Bo's manager asked around about who some of the top Midwestern comics were and my name came up. They asked me to do two shows, one here in Chicago, and one in Madison. They ended up going really well so they brought me on for the rest of the tour, and I'm doing a couple more dates in October.

The whole thing kind of came up out of nowhere, but his crowd is kind of a perfect fit. It's a lot of younger, college-aged kids, and I guess my standup is still relatable enough? I don't really think of Bo and I of sharing a similar sensibility, but it ended up being pretty perfect.

TS: You're a very funny standup, but your work experience implies your main interests lie behind the scenes, in the writer's room. Is that accurate or is there just as much of a drive to do standup as well?

CJT: I go back and forth nowadays, I think I've found a lot of success being behind the scenes, writing and producing stuff. I think my whole approach so far has been influenced by not wating to work any other job, there's the motivation to stay out of an office job, answering phones all day or whatever. 

I've always loved TV, I grew up watching Conan and SNL and wanted to know everything about them. When I found out there were writers, it seemed like an easy way in. I thought "if I write… maybe I can write myself into things!" I haven't been successful enough to do that yet, though.

Writing has been a way that I can get involved with bigger productions, that was the idea behind it. I now make a living writing, but I still love standup. I can walk away from standup for a few months, bit I always find myself coming back to it.

All my friends are standup comedians, too, and there's just so many great rooms in Chicago right now , it's just too easy to not do… If there's a forum for me to go up and do comedy, of course I'm going to take advantage of that!

TS: You mentioned you're now making a living writing. That's with the Onion News Network, correct? 

CJT: Yeah, I'm consulting for them, me and a few others from the Chicago comedy scene are consulting. Right now we're just writing a little bit, with the hopes that they'll hire us.

TS: What's the difference between a consulting writer and other writing positions?

CJT: Since the ONN just came out to Chicago, they hired a couple of staff writers, people who'd already been with the Onion for a while, and then they put together a consulting group. We were in the office for the first three weeks, doing the same jobs of the staff writers. We were at writers meetings and doing a lot of room writing.

The three weeks are up now, so now we're meeting once a week for three hours, and seeing what needs to get done and learning the different aspects of the network. It's sort of like a tryout… I think they're just feeling us out right now and seeing who they want to take on full time. 

TS: I'd imagine you were already a fan of the Onion going into this position, was it intimidating to start a job like that? How do you deal with the sort of pressure that I'd imagine would be involved?

CJT: I've always been so intimidated by the Onion, but I'd never had any sort of inkling to ever write for them, they're always so smart and biting. They have that sharp commentary on what's happening in the world. If you ask anyone who's worked with me, generally my sensibility is very silly, I'm not usually commenting on our times. 

TS: I think The Onion has a really great silly side, though, that often gets overlooked. One of my favorite things from them recently was Area Man Hurt. It's perfect.

CJT: Yeah, that one was so funny. For my submission I wrote a bunch of headlines like that. I just wrote stuff I thought was funny, so even if I didn't get it, I'd be proud of my submission. I ended up getting it and I found there is a place for that.

It's still very intimidating though... It's actually been more intimidating than any of the other places I've written for so far. I don't know it inside and out. Now I'm paying attention to the news a lot more.

TS: So you've found yourself pouring over the news looking for inspiration?

CJT: I was actually talking to someone about this… We were trying to break down our own processes to each other, and I think I just take what I know about the subjects of the stories, the presidential candidates for example, and then I think of the most absurd thing they can do that would still make sense. In my head I think of 20 absurd things things that I could do for each topic, and by the twentieth, I find something that makes sense accidentally. It accidentally sounds sort of intelligent, I come up with commentary on accident. 

TS: It's like Bill Maher lives somewhere in the depths of your psyche.

CJT: That's right. Someone in the back of my head has an opinion about what's going on.