Meet Me In New York: Megan Gailey

What do they say about New York City: There are eight million stories, and sometimes it seems as though eight million of the people telling them think they’re comedians? No, that’s not it. It is a fact, though, that America’s biggest city is also its biggest comedy mecca. Hollywood may be Hollywood, but New York City is where comedians are born funny, become funny or arrive to thrust their funny upon us. I think we should meet some of these people. This is a recurring feature, a mini-profile of newcomers, up-and-comers and overcomers of New York’s vibrant comedy scene. It’s called Meet Me In New York.

The key to making your mark in New York City isn’t all that different from the key to comedy as a whole. Timing! Megan Gailey certainly has made the most of her first couple of years since the Indiana native relocated here from Chicago — although as she told me, that’s all been “just in the last six months!” First booking New Faces in Montreal — then Conan straight outta JFL — then a spot on Comedy Central’s stand-up showcase, Adam Devine’s House Party, and now a starring role in an upcoming MTV sketch comedy series, Ladylike. I have such a fond memory of meeting Gailey’s mother while waiting in line at Just For Laughs, then knowing just how special it was for Gailey to name-check her during her big breakthrough performance. I managed to catch up with her over breakfast at Le Pain Quotidien in Midtown before she flew out to Hollywood to finish out her first “pilot season” there. Let’s get to know more about her before Hollywood takes her in full-time, then!

You can listen to Megan Gailey’s interview in her own words by contributing to The Comic’s Comic via Patreon.

Name: Megan Gailey
Arrival Date: May 2014
Arrived From: Chicago

When and where did you start performing comedy? “The first time I did it was September 24th, and I remember that because my best friend from high school and one of my best friends from college, both of their birthdays. And it was in Indianapolis at Crackers in Broad Ripple. And I wore a vest. And I’m so embarrassed. I still look at it and I’m like, ‘What was I wearing?’ But I wanted to have a cinched waist. So I was like, you know what? White T-shirt, black vest. Nothing will look more Paula Poundstone but give me a little hourglass shape. And I did it and it was great and I had no fucking idea what I was doing. But I did well because it’s not that hard to make hillbillies laugh. You know?” What was that show at Crackers? “So they actually do a very good booked open mic. So I remember the first time I went, because I had heard of open mics, so I went to sign up, to like do it that night. And they were like, ‘Oh, no. You sign up for like a month in advance.’ And I was like, ‘Oh!’ And even then, I was well, that seems odd. So I signed up a month in advance. But they have people come. Back then, it wasn’t like a bringer. Now I think if you’re going up, you have to bring five people to get on. But back then, people just came, because they had enough working comics that would do that club. And it was free for college students that night, or whatever. So it’d be a packed house for an open mic.”

What was your best credit before moving here? “I don’t know if I used one…I had done Just For Laughs Chicago. I had been in Chicago Magazine. Anything sort-of Chicago related. I don’t think I, whenever people would ask me, I’d be like, ‘Nothing.’ Truly nothing. Just tell them I’m a woman. They’ll like it.”

Why did you pick NYC over LA or anywhere else? “I was always going to go to L.A. and then I had sort of an influx of friends that came here right before I was leaving Chicago. And then I moved here with Liza Treyger. And she always wanted to come here.”

“And Liza and I were very close, we’re going to live together, we’re going to live in Kenny (DeForest) and Will (Miles) and Clark (Jones)’s concrete basement in Bushwick, and thought that was going to work out. And then we got here and it had flooded. And so we could not live there. But I think, I like to pretend that the reason I moved here was because this was where stand-up comedy lives and I’d be like, if I’d just gone straight to L.A. I would have felt like I’d skipped a step. But the real truth is I just had — all my friends were here and I wanted to be by my friends.”

How long did it take to get your first paid gig in NYC after moving here? “Well, I was nannying.”

Well, paid stand-up, I mean. “That was a hard thing for me, because when I was in Chicago, I was basically just doing stand-up for the last two years. I would waitress and bartend maybe a couple of times a month, and most of that was because I loved the place I worked at. And then when I moved here, I made no money doing stand-up and had to go back to working full-time. And then, I mean, I don’t think I ever got paid to work here! I kinda stopped doing the road, here. I guess I got paid at some point, but I truly have no recollection of what it was. Maybe a Caroline’s show, where I got a sandwich and they handed me a wad of money afterwards. And by wad, I mean a bill. One bill.” Yeah, well they make $100 bills. “It was not one of those. It was like a $20. But even when people hand me a $20 bill now after a show, I’m like, ‘Thank you so much!’ Like, I’m truly delighted. This is so sad.”

How is this scene better/same/worse than the scene you moved from? “I was only in Indy for a few months, and I did it very — I maybe went up like four times before I went to Chicago…I think I just knew, I don’t know how I knew this, but I just knew you needed to be onstage constantly when you were starting. For me, I didn’t feel like I was going to be able to do that in Indy. There’s people that do. I just, at that point, somehow, nah. So moving to Chicago was probably the best decision I’ve ever made. When I got there, there were lots of shows. Some of them were OK. Most of them were pretty bad. But there were mics every night. And the scene was small enough that you kind of knew everyone. It felt very overwhelming when I first got there. Who were these people? But then over the course of a few weeks or months, OK, this group of people are friends, and you sort of figured it out to the point where it grew so much over those six years, that every night there’s great shows, and you go to open mics, and you’re like, ‘Who are those people?’ There were just constantly new people cropping up. And I think a lot of that is, probably because of, it became a destination, I think? To go get good in comedy, where no one really cared. No one watched there. Industry was never there when I was there. Maybe you’d hear, ‘so-and-so’s agent is coming to see someone,’ but you would hear that maybe once every two years. And then when you would do Montreal auditions, that was sort of the most contact we ever had with industry. So you were kind of in this protected umbrella of no one really caring, in a good way. Or coming to watch, or trying to pluck people out of it, and you could just be a lunatic and be bad. And be a drunk. And figure out what you wanted to do, wanted to talk about.”

How would you compare that to New York? “In Chicago, I never heard people be like, ‘I’m trying to get my TV five.’ The focus was never sort of those goals. We’d be like, maybe I’ll get a Montreal audition. You just felt so removed from it. It was just, do as many sets as possible. Get as funny as you can. Maybe you’ll get to go to Naperville and do a show. And it was just a little simpler, I think. And here, I think people are definitely, I want to get funny, I want to do sets…but you’re just closer to people who have done stuff that’s cool. So you’re like, oh, wow, I didn’t even know that was a possibility. So I think your mind begins to like wander a little bit. But you’ll have mics where it’s like, yeah, these people have been on TV tons of times, and these (other) people clearly have no idea what they’re doing. So there is no middle class.”

What tip would you give to any comedian who moves here? “I got really caught up in this thing, where I would hear people say they were leaving whatever town they started in after like two years. And I’m like, ‘What are you doing?!’ I can’t be upset with people just because they didn’t do it the way I did it. I think just come here and try and be funny. I remember people being, ‘you’ve got to do your A jokes at open mics.’ And I’m like, ‘That’s not why I go to open mics, though.’ I guess, maybe, if that’s what you want to do to try and get booked on stuff, do that. But also, this is a really good place to get funny as well. There’s a ton of stage time. And there are very interesting, cool people that do wacky, weird shit like I never even saw in Chicago, or anywhere. So come not with a pretense of I want to get this and this and this and this, just come and try and soak up as much of the cool, fun stuff that’s happening around you.”

Can you describe an “only in New York City” moment from your experience here? “I was on the train on Halloween, and there were all these little kids. But this a Sunday, so it wasn’t like drunk-drunk Halloween. It was like kids who’d been trick-or-treating. And so, a crazy man just stood up and started fighting with a not-crazy man and then punched him. And then the not-crazy man ran off, and got the police. But in the midst of them trying to figure this out, they locked us in the train with the crazy man. In the station. And so there were people on the train who had flights to catch, or, you know, going somewhere. So in true New York fashion, stand up and start screaming at the crazy man who they’d just seen assault a stranger, ‘You piece of shit! Clink clink! I hope you like it in Rikers! You’re going to get raped!’ Like, going crazy. And I’m, he’s clearly mentally disturbed. And you’re antagonizing him. I got to the point where, I feel bad for him. And these people were the quote-unquote ‘normal people.’ The ones traveling for business. Just shouting at a lunatic. And then the police came and they got him off, and then everyone cheered. There was a little girl in a Frozen costume, who asked, ‘Daddy what’s going on?’ This is where I’ve chosen to raise my family, honey.”

Where do you see yourself five years from now? “I think I would like to at some point, really have a family. I don’t know if that’s in the next five years, but I would like to have a baby.” Just for the material? “Yeah yeah yeah. Just because people love pregnant women on TV. They’re like, ‘Get more fat women up there.’ Not that pregnant women are fat. They look beautiful, they’re glowing. I would like to have some sort of creative stake in a show, whether I’m writing on a show, or helping do something in some fun, wacky way. And then I would like to be acting to some extent. And then just doing lots of fun stand-up. But also not fun stand-up. That’s good, too.”

Ladylike debuts on MTV in June.

In the meantime, when Gailey is in NYC, she helps produce and host “The Front Room” Wednesday nights at The Knitting Factory in Brooklyn. You can find her other touring dates on her website at And you can follow her on Instagram and Twitter.

Here’s her debut on Conan from October 2015:

And earlier this year, a clip from Gailey’s appearance on Adam Devine’s House Party:

Which NYC comedian would you like to see me style and profile next for Meet Me In New York? Send your nominations to: thecomicscomic AT gmail DOT com

Top: Photo of Megan Gailey at SXSW 2016 by Mindy Tucker

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

View all posts by Sean L. McCarthy →