Emma Willmann Thinks ‘Crazy Ex-Girlfriend’ Is Changing Her Comedy For The Better

Mandee Johnson/Uproxx

When Netflix drops its previously announced collection of 15-minute stand-up comedy specials later this year, Crazy Ex-Girlfriend season three addition Emma Willmann will be among them. The Blue Hill, Maine native also popped up on the latest season of Pete Holmes and Judd Apatow’s HBO show Crashing this year, all while co-hosting the popular Inside the Closet podcast with fellow comic Matteo Lane. While Willmann’s star is fast on the rise elsewhere, she remains one of the country’s most innovative and enjoyable comics, which she’ll prove again at this year’s Women in Comedy Festival in Boston.

Ahead of her headlining show at the Brattle Theater on April 20th, I spoke to Willmann about how her comedy career has flourished so quickly in the past few years. Much of her success, she tells me, has to do with the time she spent cutting her teeth in the Boston comedy scene, then later at New York’s Comedy Cellar and other established clubs. That being said, Willmann can’t shake the thought that Crazy Ex-Girlfriend is already affecting her comedy. “She’s inspiring,” she said of Rachel Bloom. “From a writing standpoint, it’s inspiring that someone’s creation can be that smart and that good, especially since there’s a home for it.”

You were just in the new Comedy Cellar location in Vegas. How was it?

I actually loved it. I have never been to Vegas before. I opened for Louie Anderson at a casino in Reno. We did like a 4 pm show and 7 pm show. It was either for the high rollers, or I think what it was actually for was the people who had lost so much money and got a free comedy show. They had a name for them. Before I went out, Louie goes, “These people, they’re trying to distract them because they lost a lot of money.” So I did that and didn’t really think one way or another about it. But doing the Comedy Cellar in Vegas, I just really liked it. I didn’t even want to come back to New York.

I don’t know why it liked it. I try to eat healthy, but that’s not the Vegas way. It’s all gluttony, but I liked it. The way the comedy show was set up is, they set up a room just like the Village Underground back in New York. It has low ceilings and similar lineups, and the comics aren’t changing their acts. It’s the audiences who are different each time. It’s definitely a different type of crowd than the ones that go into the rooms in New York, but I really liked it. I really hope it’s successful.

You’re going back in May, right?

Yes. They’ve got it booked out for a little bit. I mean, the room is awesome. They even have one of the main Cellar staff members there, the general manager, Liz Furiati. She’s living in Vegas right now. I was like, “Are you alright?” She was like, “Yeah, but I’m not living out there forever.” The thing is, what makes the Cellar the Cellar is they do all the little things to treat the comedians really well. I definitely felt the same care I’d felt in New York out there in Vegas.

I was curious, because the Cellar is a famously small and intimate setting, which seems antithetical to Vegas.

Have you been to the Village Underground location in New York?


It’s like that. They set it up like that and not like the one on MacDougal. It’s more like a showroom. It’s still a showcase club, which is why I think it felt more like a vacation. That’s nice because normally when you’re on the road, you’re doing 45 minutes to an hour. When I’m doing 45 minutes to an hour, I really have to think about it. And if you’re doing one after the other, it’s like, “What did I say already?” It’s a real emotional undertaking. But doing 15 minutes with four or five other people is awesome. I was there with Julian McCullough, Emmy Blotnick, Greer Barnes, and Rich Vos. It was a great mix, and plus it’s still the Cellar brand, so it’s not like your name is on the show and the crowd size is totally up to you. The responsibility is spread out.

Does it feel that was with larger festivals, like Boston’s Women in Comedy Festival? You’re co-headlining it, but as you say with the Cellar, it’s not all on you.

It’s definitely more like a community, because there are plenty of people that go to festivals like Boston’s every year. Especially with the way Boston does it, too, because they have a lot of panels, events, and after parties in addition to the shows. It was neat because in New York, and pretty much in Los Angeles now too, whenever I go I’ll see the same 50 comedians around. It’s similar to going to Boston, because I’ll see a lot of the same Boston comics around. You just get familiar with people’s sets and all of that. But the two times I’ve done the Women in Comedy Festival, I saw a bunch of people I had never seen before. That’s always fun. It’s nice to see new stuff.

You’re originally from Maine, and you did stand-up in Boston before moving to New York. Does performing in Boston feel like coming back home?

I love it. It’s like my favorite. Also, the thing with Boston is — and I was surprised that Portland, Oregon was similar — it’s a mix of blue-collar people and visitors who are out to have a good time. There are definitely the splashes of San Francisco yuppies and similar types, too, but then there are people from Southie. It’s a real mix. Boston isn’t known for being the most racially diverse place, but class-wise, there’s a real mix of people there. Boston is pretty blunt, and Boston likes comedy.

Boston comedians and comedy show audiences are never really shy.

Yeah, they’re definitely not shy. I don’t know why this is. Maybe it’s the Comedy Studio because the owner, Rick Jenkins. It’s one of the places Boston comedians really gravitate towards because, I don’t know if he’s doing this at his new location, but he used to have a thing where if you go to three shows — one weekday, two weekends — he’d give you a spot on a Wednesday. And because he had that policy, he also became one of the people that most comics would seek advice from first. He would always say, “It’s about the jokes. You have to have original jokes. Jokes, jokes, jokes!” I don’t know if that’s where it’s coming from in Boston, but I feel like with Los Angeles comedians, the stereotype is that they’re more performery. As for Boston comics, I always think of them as really good writers.

Do you consider yourself more of a performer or a writer?

I feel like so much more of a performer. The thing I feel the most self-conscious about is the writing. In my head I’m always like, “I have to fucking sell it!” That’s what I think about that most. Whenever I see other comics I’m like, “Man, they’re a good writer.” I’m always writing or rewriting, or thinking about the writing or the rewriting. I always get self-conscious about it, and I’m always worried it’s not going to work out. That’s why if I’m in a bad mood or just tired I get nervous. I’m like, “Oh no, I’m not going to seem friendly, and if I’m not friendly, I’m not going to be able to sell it.” That’s definitely something that goes through my head a lot. I think about the energy behind the words. I feel like I think about the most, and because that’s where I put so much of my intent, I end up thinking about the writing second. That’s why I feel so self-conscious about it, even though I actually do love writing. Not the editing, though. That’s all fat.

I’m sure most professional writers dislike editing.

That’s good to hear. I like shared misery.

Speaking of writing, these days it seems more and more comics are relying on their phones to record shows, take notes, or both. Is that what you do, or do you write everything out George Carlin style?

I really think the best way to do it is to actually sit down and write everything out. It’s the most tedious, because a lot of time you forget what you said and when you’re writing it out you’ll go, “Oh wow. I didn’t realize. I could have made that a lot shorter, or I could have put this there.” It works, but it’s also the most tedious way of doing it. I’ve tried everything. I can’t tell you how many other tasks I’ve done to avoid listening to recordings, or just telling myself, “I don’t need to do that.” I’m not great about it, but listening to recordings is also one of the most helpful things. You go onstage to say stuff, and sometimes you’ll say new things. Like if a show is going really well and I’m getting excited, I’ll say something I haven’t said before because of the energy wave I’m riding. Then I’ll go back, listen to it and say, “I can say that again.” Then again, maybe it just worked that one time because the crowd was really good, so when you go back and the show’s not going as well, or it’s a tighter audience, then you can ask, “Does this actually work or was just working for them?”

I used to write about anything that I thought was weird or odd, or anything I thought was funny. But then it became too hard to loop everything together, because it wouldn’t necessarily be something personal. There was a long time where I was really trying to write about Groupon, or I was really trying to write about boy bands, and then I realized it was too hard to fit in all the rest of the stuff I was doing because it didn’t make sense. When it’s just an observation, it’s tricky because so many people can do observations like it. And if someone else can do it, then it’s not that profound of an observation. They might even be able to write it out better. So I usually opt for more personal stuff because that’s easier to incorporate. The process now, just because I have a set that I have been doing, is whenever I’m doing a longer set, I try to add things on to already existing stuff, then go back and listen to it. Pretty soon I’m going to need to scratch that and try something new, though, because I have 15 minutes coming out on Netflix in June, and I have six new minutes that I created by adding to pre-existing stuff. Now I need to figure out a way to have that work as a standalone.

For most comics, once something is taped and out there, they’re done with it. Is that how you feel about it?

Yeah. You start to feel weird about it. I used to always open with the same thing, and then I did that on The Late Show with Stephen Colbert and stopped doing it. I would still do the other four minutes I did on Colbert the year following that, but now I don’t really do it anymore. And it’s tough, because having some old material helps gauge how well or not the new stuff is doing. It’s also like a muscle memory thing where you’re just automatically doing or saying things because you’ve done them so many times before. When I did my Colbert set, I remember that two weeks before, the booker, Jessica Pilot wanted to change the wording on something. It was a little change but I only had a couple of days to practice it. And even though it was such a slight wording change, because I had said it so many other times the other way, trying to change it became such a brain cramp. If worked out, but I struggled with it. The change made much more sense, so Jessica was right. But I struggled. I was like, “Uggghhh.”

[Laughs.] Sorry. The voice you use for you mother creeped in there and I couldn’t help it.

[Laughs.] Yeah, it’s my only voice.

I wouldn’t say it’s your only voice, but it’s one of my favorites.

I really appreciate that, but yeah, it’s my only voice.

What are you looking forward to at the Women in Comedy Festival?

One thing I like about doing shows in Boston is, it’s just nice. A lot of times, comedy can be very lonely. You’re out there by yourself, traveling and doing shows, so it’s really nice to have other people around. I feel like the Women in Comedy Festival and Just for Laughs in Montreal are the two festivals I’ve gone to the most, but Boston feels more like a nice community check-in. It’s just nice to see everybody there, to see the Boston comics, and hear and watch what other people are doing. To see what people are working on. I’m excited about that.

Also, my sister had a baby, so I’m going to go see the baby after the festival. Hopefully I’ll get some new material from my mom. She’s coming to the show on Friday. She’s like, “How many new jokes do you have? Now that you’re getting more famous, don’t you need to have new material?” She’s been saying that for the past two years. She’s like, “Does anyone say anything new? You do the same jokes a lot.” I always tell her that I’m working on it, so that always stresses me out.

Is that her subtle way of saying, “Don’t tell as many jokes about me”?

I know, right? It’s also funny because sometimes after shows people will go, “Your mom is so funny!” I want to be like, “I’m making it up. It’s true, but it’s embellished. That’s how comedy works.” But then people will say, “Your mom should be a comedian!” I always appreciate that, but then I’m also thinking, “No, I spent a lot of time making that up.” It’s funny how, because she is like that, but it’s also exaggerated for the sake of the jokes and the stories. She’s not really like that.

That’s how storytelling, especially among friends and family, generally works. The same stories get told again and again, and embellishments are added with time.

One hundred percent.

By the way, a belated congratulations on Crazy Ex-Girlfriend.

I’m glad that people are really into Crazy Ex-Girlfriend. That show is so well written and so much fun.

Pretty much anything Rachel Bloom touches is gold.

I got to hang out with her at the GLAAD Awards last week. She was awesome. It was the most we’ve hung out since filming. She’s inspiring. From a writing standpoint, it’s inspiring that someone’s creation can be that smart and that good, especially since there’s a home for it.

Has it inspired your writing?

It really has. I think her and the show’s co-creator, Aline Brosh McKenna said somewhere in an interview something like, “We made exactly the show we wanted to make, and we didn’t sacrifice integrity or plot or anything. We just created the exact show we wanted.” And that is hugely inspiring. They were able to make the show they wanted, find a home for it, and find an audience for it. People really respond to it. When I first started reading about script writing, I would almost write things like, “What would someone want to hear?” If you really start to scale it back, it’s kind of freeing to try to write something that doesn’t operate like that. I can’t imagine how hard it would have been to pitch a musical show. That’s so different. If she could make a funny, good musical, then I have to at least try to write something.

Not just pitching and writing that, but producing and maintaining it for three seasons, and now a fourth one.

I’m so impressed by the singing because it’s just so different. I saw Crazy Ex-Girlfriend Live in New York and I was blown away. It’s so funny and theatrical, and it’s all song-and-dance stuff. I had a show later that night, and I later realized I was being much more theatrical in my delivery. It’s inspiring. That stuff was coming out at my show. It’s infectious.

Emma Willmann will be at the 9th Annual Women in Comedy Festival in Boston April 20th-22nd. New episodes of her and Matteo Lane’s podcast Inside the Closet are posted weekly.