Megan Gailey performs at Schubas on Fri 7/22. Credit: Courtesy the Artist

In the two years since she left Chicago, Megan Gailey has boosted her recognition with shows across the country, a spot on Conan, and a starring role in MTV’s prank show Ladylike. Now she’s returning to the city where she cut her teeth to headline the Comedy Exposition. We talked with the stand-up about her first time onstage, drunk Chicago comics, and reading YouTube comments.

Last year you showed up for the Comedy Expo thinking you were headlining, but you actually ended up hosting a night of comics instead. How does it feel to officially be a headliner this year?

Last year was so fun. When I got there I was like, “Oh, OK,” and then it ended up being so much more fun for me because I got to introduce friends and make fun of them. It was almost like they were giving me my own party to host. This is my third year doing the Comedy Expo and I love it so much. Chicago is always so fun for me, but especially to come back during Expo, when there are other people who have also left Chicago and are visiting, it’s like a fun, drunk reunion.

After the Expo you’re also returning to Crackers, in Indiana, where you did your first stand-up set. What was that first night onstage like?

Oh my god, I wore a vest, which I look back on like, “What was I doing?” I think I just wanted to have a really thin waist so I just wore this pinched-in tight vest. I have a theater background, so I knew at least how to talk in front of people. I did much better than I deserved to, but it was terrible. It was an open mike and I had a bunch of friends there, and we all went out and celebrated after. I went to two open mikes just last night, and it was so bleak.

How old were you when you started doing comedy?

I was 23, and now I’m 30. I used to say to myself that if I didn’t feel like I had made significant strides by the time I was 30, I’d stop. But the thing is, you constantly accomplish something and then are terrible at something. At this point I can’t stop—I’m addicted.

You’re on TV quite a bit now, that’s got to feel like a significant stride.

Someone asked me recently if it’s validating, and oh yes, it absolutely is—if not for yourself, then for other people. If I die, it’s like, “Oh, cool, here’s this clip of me.” Luckily, for the MTV show we have hair and makeup and wardrobe, so I always can be in a fun outfit and look good, and every time I see myself there hasn’t been a time when I’m not like, “Oh no, my arm is so fat!” Even people on YouTube have commented that I have fat arms.

Never read the comments!

I know, but they’re so funny! Once a man said that he wanted to choke me and have sex with my dead body. And it’s like, what?! I was onstage for five minutes, how did you get to that point?

Tell me a little bit more about your MTV show, Ladylike.

This one is a hidden-camera prank show. I think they like to think of it as a feminist version of Punk’d. It’s an all-girl cast and then there’s Matteo Lane, who’s also a Chicago comic, and we just go around and harass people in New York City with the idea of “Boys always get away with this stuff, why can’t girls?” It was very nerve-racking to film because I don’t like people being mad at me, and I go into every situation trying to make someone the most mad at me.

What’s one of the worst situations you’ve gotten into?

Three people tried to fight me throughout the filming. You have an earpiece in, because they give you some logistical directions sometimes, and I would have someone be like, “I’m going to fight you!” One girl once said, “Bitch, I’m from Chicago, I’ll kill you,” and I was like, “She means it!” But I always thought that I’d be in danger and the producers would say, “Tell them it’s a prank and you’ll be fine!” But, no, once they hear that, they’re like, “OK, now really go for it.” My mom, every day, she’ll ask, “Are you safe? Are you OK?” We’re harassing people in Times Square—it’s scary.

So just in the past two years you’ve gone from Chicago to New York to LA—that’s a lot of different comedy scenes in a short amount of time.

It is, it’s weird. They’re all different and fun, and all have drawbacks and positives, but the nice thing coming from Chicago is I have so many friends in LA and New York, so when I got to both places it felt like I had a built-in support system already. And people hate us—we’re so annoying about being from Chicago. We’re the loudest and drunkest and craziest. And people will try to be nice, “Oh, you Chicago people are all so funny! You’re mentally ill, but you’re funny!”

How are you preparing for this headline set?

I’m just going to try my very best [laughs]. When I’m in Chicago I tend to tell a lot of stories about my time there, even stories that are more insane than I realized at the time. I think when you’re in that bubble you’re like, “Oh, yeah, everybody falls asleep on the sidewalk.” When I go back I tend to be very reminiscent and nostalgic about how great it was and how much I loved living there.

What other projects are you working on right now?

I’m currently filming a webseries for the Kicker, which is part of Above Average, Lorne Michaels’s digital platform. And I’m going to Beyonce in September. That’s really what’s keeping me going right now.  v