What did doing a Half Hour mean to you?
I mean, when I started doing comedy, pretty much my only goal was to do that. That was my introduction to standup. I think it started in 1998, I was in 7th grade. All I had known about comedy before then was The Simpsons, and then I got like really into Comedy Central Presents. When I started comedy, it was very much like, I really want to do that. I was really cool to do. Now I’m retired from comedy.
If people don’t know you as well, what’s your typical gig like? Are you on the road, are you doing colleges?
For some reason, I do not do colleges. I don't think I know how to talk to—even when I was 23, I didn't know how to talk a college-age kid at all. So mostly, when I lived in New York, I did only the downtown like alternative rooms, and since I've been in LA I've been doing a lot of road stuff, which is cool. I like both of those things.
And I know you’ve also written for television.
Yeah, I've done television writing. I wrote on Sports Show with Norm McDonald and The Ben Show and Upload with Shaquille O'Neal. Yeah, I really like that too. It gets me to not fly. I don't like flying.
That must make road work difficult.
It does! It really does. It turns out, most of the road work is flying for me. The shows are fun and even the hotels are fun, but flying to the location really makes me rethink every decision that I've ever made in my entire life.
You also do sketch comedy. How do you separate your sketch and standup material?
I have trouble separating everything, so basically if I'm doing one thing it's really affecting the other thing in a negative way. I'm just kind of ignoring it. But I know there are people who can think of something and are like, “Oh, I could do this in anything.” But not me. I think it's because my personality is so awkward on stage, that I can't do observational jokes at all. It all has to be just about me. So sketch is fun because then I can be like, “This isn't for me. This is for a fake person.” I like that.
Do you find doing all those other things ends up informing your stand-up?
I'm not 100 percent sure on that, but I think it does. It gives you like a sense of confidence in what you're saying. Like in a writers’ room, you learn how to actually pitch a joke in the best way. Or else you are going to be fired. And podcasting is having fun connecting with another human being, and that's really all standup is. I think. [Laughs] I've always said that standup is just connecting with another human being. A group of them.
In your generation of comics, it’s become so standard to do lots of thing, when even 10 years ago there were a lot of people who just did standup. No one coming up now does that.
Yeah, its kind of weird. When I started, and I think like everyone who did it this year started at a similar time, it was really was the beginning of internet comedy. So it’s just like, we can do whatever we want and it doesn’t matter. And most of the time, I'm so glad it was the beginning. A bunch of terrible things I did will never be seen. It’s just really deep on the internet.
And yet, there are still these traditional steps in a standup career, like late night spots and half hour specials that people still do, while doing more personal things on the elsewhere.
I'm glad that you can still do that. I doesn’t like break you in the way where it did like in the 70s or 80s, where like you would do it, and then, “Hey, you're Jerry Seinfeld. Congratulations.“ But you're just doing something that you grew up watching. I just want to do everything I grew up watching.
Anything in particular you have in mind?
Like the half hour. Conan was really big. One of my only other things that I haven't done that I really want to do is write for SNL. That's basically it. And then I would like to ruin all my childhood movies by remaking them one day.
Any one in particular?
Monster Squad. I'd love to do Monster Squad.
What comes next for you?
Um, there's some things I can't talk about, but then there's other things. I'm in a sketch group with Sam Brown from The Whitest Kids and James Pumphrey, and we do things on the internet that people can check out.
Sean O'Connor's Half Hour airs Friday, May 17 at 12:30 am.