Comedian and producer Emily Winter moved to New York in 2007 and shortly after arriving, walked in on Stephen Colbert in his underwear. Over the next decade or so she worked on a yacht, raised over $50k for the ACLU, was featured on The TODAY Show, and began writing jokes for NPR’s "Ask Me Another”. There’s a lot more too, check her website out. Before COVID-19 shut the world down, she was gearing up to co-produce the 2020 Brooklyn Comedy Festival. We talked about all that and more on April 6, 2020. We are not sure who connected us; maybe Katie McCarthy? In any event, she’s cool shit and I’m glad to now know this person. Got my fingers crossed that One Liner Madness stays on the books at The Bell House this July. Emily: I didn't realize you're in New York, too. Okay, great.
Ben: Yep. Where in the city are you?
Emily: I live in Red Hook.
Ben: Geographically close, yet so far by public transit. What’s the mood like there? How are you doing?
Emily: My husband and I are both healthy. We're fine. I mean, one of my jobs was event managing for a comedy club on the Upper West Side. I was trying to sort of turn the club around a little bit and they not only stopped paying, they just stopped talking to me once all of this hit. So that really sucks. But I got really lucky in that I'm publishing a book so I have something to work on, and it means some money coming in which is great. The mood down here is probably the same as it is everywhere. People are wearing masks but also, I went for a jog to Brooklyn Bridge Park today and it was mob. It was really packed, tons of bikers. I think people are crawling out of their skin and wanting to get out, but everybody seems to be trying to maintain safe distance.
Ben: Are you a native New Yorker?
Emily: No, I'm from Illinois. I moved here in 2007 to intern for the Colbert Report. Brooklyn’s my home now.
Ben: Moving to New York with an interest in comedy and ending up with a first internship at Colbert...that is a good move. How did that happen?
Emily: After I graduated from the University of Wisconsin-Madison I got a job as a newspaper reporter. I was a journalism major but I really hated it. I realized that I loved to write, but didn't want to write news. I never thought about comedy writing as a job but had been working on a script about my college newspaper. I moved home to my parents house in Illinois and took a script writing class at Columbia College in Chicago where my teacher encouraged me to apply to internships. So I did. That is how I got my internship.
Ben: What was the experience like there?
The crowd for What a Joke at Rough Trade Records in Brooklyn, NY. Photo provided by Emily Winter.
Emily: You know, I had such insane luck my first year living in New York. Really, total beginner's luck. I had no concept of how competitive and hard the world really was. Since then, I've definitely gotten the shit kicked out of me. But yeah it was an incredible experience. He [Stephen Colbert] was so nice. I walked in on him and his underwear on my first day of the internship and thought I was getting sent back to the Midwest. He was very funny and sweet about it. There, I just learned how it all functions. I knew I needed to have one of those writing jobs. I was also waitressing at an Irish restaurant in Times Square— which is the most miserable job on the planet —and one of the other interns hooked me up with a job as the assistant to a contributing editor at Vogue. When I finished my internship I just went to work full time there.
Ben: That is definitely some beginner's luck right there. And after Colbert you were working for a book packaging company?
Emily: I did for roughly a year. I also worked as a mate on a yacht.
Ben: Just scanning Craigslist and you see “Yacht Mate”?
Emily: I had a friend who was a first mate. We're all out one night and I mentioned that I’d just had to sell my moped, so he let me know the yacht was hiring. It's so weird. When I was in college— I thought this was true of all colleges but I guess not —at the University of Wisconsin-Madison almost everyone has a moped. So I lost the moped but got hired on the boat.
Ben: Sans-moped and post-yacht, you worked at what seems to be sort of a Cliff’s Notes type company?
“ I wasn't getting booked on any shows because I was new. And also very bad.”
Emily: Oh, SparkNotes. I worked at SparkNotes for six years and when I left I was the Editorial Director. It was the closest job to comedy that I could get, we were working on a funny blog for teenagers called Spark Life. I worked with some other editors and we built up the blog, it was really fun. But during my tenure there I started trying out comedy more ‘cause I was like, “I need to do whatever it takes or I will die in this cubicle.”
Ben: Did you have more beginner's luck with comedy? You just walked into Union Hall and said “Got any open nights?” Also, I read in another interview that the first joke you wrote was in response to an assault?
Emily: It feels cathartic to talk about, thank you. I don't talk about it often. I experienced a sexual assault and then I wrote a joke, about the rape. I was just so depressed. I talked to my sister, I talked to my best friends. I just couldn't get over how upset I was and then I wrote this joke. I just really wanted to tell the joke because I was so proud of it. I was making lemonade out of lemons. I signed up to take a standup comedy class and told that joke at our graduation show. It was, um, very uncomfortable. I did not have beginner's luck with standup. I was deeply uncomfortable on stage for the first two years at least, I don't think I'm really a natural performer. And I’m not really drawn to more deadpan humor. I really like somebody who's alive on stage, but it took me a really long time to get there.
Ben: When you're on stage. Are you actively thinking about where you're standing and the pacing? Are you super in the moment or is it all very planned out?
Emily hosting One Liner Madness, an event organized by her comedy group Backfat Variety to benefit Shelter. Photo provided by Emily Winter.
Emily: I think I definitely was more sort of conscious for the first years that I was doing it. Now I think not. Now it's a flow, you know? It's like a dance or something. If you overthink it, you don't do it right.
Ben: Around this time you began writing work for TV Land. Is that where your standup network expanded?
Emily: There were some coworkers at TV Land that did standup, But by that point, outside of day jobs I already had you know, my group. You know what I mean? I had found my people.
Ben: Where had you found them?
Emily: Open mics. I also found my husband this way. It's tough…really hard. I wasn't getting booked on any shows because I was new. And also very bad. I asked a friend who had been doing it for a while and he was said, “You need to start your own show.” So six months into comedy, I started Backfat with a friend. That show is now eight years running. We started it at a place called 61 Local in Cobble Hill.
Ben: Oh Okay. I thought that show was always in Gowanus.
Emily: We did five years at 61 Local. I brought in so much business for them, and we never charged or anything. But our show was just at the point where we should be charging, we should be paying ourselves somehow. 61 Local wasn’t going to pay us, and they even took our drink tickets away. We would pack that place out.
Ben: I’m not really familiar with that room…how many people were coming out?
Emily: It would often be 60-75 people. A bunch of times like 100 with people going all the way down the staircase, just sitting in the little cubbies where they kept the chairs. I was feeling a little under-appreciated so I reached out to Union Hall and they were just like, “Come on over.”
Ben: Those feel like solid numbers for a monthly at a venue that’s not exclusively for comedy. Who were bringing in as headliners?
Emily: For our first couple of years our numbers were due to the fact that my co-producer and I spent a good chunk of our twenties in New York making friends that were not comedians. So when we said “Hey, we have a monthly show,” the people we knew came out in droves. Most comedians don't have that luxury. I don't anymore.
Emily on stage performing to a packed crowd at The Bell House in Brooklyn, NY. Photo provided by Emily Winter.
Emily: I think we are really careful producers. We don't make the show go on too long and we really put our heart and soul into everything. We try to make people happy and comfortable, and always choose comedians we think are really smart. Early on, even though our own comedy was bad, we were giving people a good product.
Ben: What is most challenging about being at a venue for five years? The same train stop, street, room, each time for five years?
Emily: We used to put so much work into every show, doing these sketches and scripting everything out to a T. I find that so funny and ridiculous. Producing a show was hard and every time you're nervous no one's gonna show up. Booking is sometimes really hard. Sometimes it’s great and you get the four people you wanted...sometimes people are not available or don't get back to you, it makes you feel bad. Or a headliner drops out the day before...that feels terrible. I've also run a weekly show [Side Ponytail] at a bar called Friends and Lovers for several years and we have the same problems. Booking and promoting is a tedious thing but if you remember how fun it is, it can always be fun.
Ben: Around the time you moved Backfat to Union Hall, you produced a multi-city festival called What a Joke and raised $50k or $60k for the ACLU, yeah?
Emily: I don't remember our total. I think maybe it was just above $50k. After Trump was elected, everyone of a sound mind was in the same sort of mood. I couldn't just be sad, it would drive me crazy. I needed to take some sort of action. So I reached out to another comedian in Brooklyn, Jenn Welch, who is a real badass. I asked if she wanted to do something and…we did the festival. We did some New York shows and then oversaw everybody else's. Shows all over the country with comic friends who were also mad and wanted to do something. It entailed finding producers in every city who wanted to be a part of it, getting everyone on the same page, streamlining the graphics. and making a video together. It was really amazing to see photos of my friends all over the country going to a show that I was producing.
Ben: Were there specific guidelines or did you just ask people to throw some comedy shows and donate profits to the ACLU?
Emily: It was a mix. It was important that there was a uniform look and feel to the promotional stuff. It was important that we didn't book shows that were all white, you know what I mean? We wanted diversity and everyone was really on board with that. All tickets could be purchased through our website, too. But we weren't telling everyone who they had to book exactly because the producers in those cities know their own markets. We had a publicist who got us interviews all over the country, but we also encouraged the city producers to reach out to their local media.
Ben: So you raised a decent chunk of change by producing this multi-city festival, but then the next year you made a resolution to get 100 professional rejection letters. It seems you should have been riding high, why was that the move?
Emily: I wasn't out there trying to make producing events my career, it just wound up being part of [it] through comedy. Basically what happened was that I was up for a job at The Daily Show as a writer. I’m sending in these exhausting packets. Rounds of packets. They asked me to come in for an interview and I thought, “Holy shit. This will be my job for the rest of my life.” And then, I didn't get the job. So I just embraced it with my year of rejection.
Ben: Did the experience of cataloging rejection letters make them feel less personal? Every letter became a win no matter the contents, right?
“I'm going to write my way out of this.”
Emily: Yeah. That's exactly what it did, it made every attempt to further my career and better myself a no-lose situation. I either got something, which is great, or I didn't but got to put the rejection on my list, which furthered that project. It was a way of taking control of being in the entertainment industry, which as we all know, is just such a crap shoot. I made it positive because it really can be demoralizing.
Ben: Did you end up getting all rejections or did you end up with a lasting gig before you hit 100?
Emily: Um, I got 107 rejections.
Ben: Congrats on exceeding your goal?
Emily: You know, it was fine. I'm so glad I did it, and I got 43 acceptances which I don’t think is so bad.
Ben: Was one of those positive returns how you ended up writing for NPR’s Ask Me Another?
Emily: Yes. I applied to be a writer there that year, and I was so thrilled when I got it.
Ben: What’s comedy writing for a game show actually look like? Do they give you topics and you keep trying different puns out?
Emily: Most comedy writing jobs are full time and you're in the office everyday, all day. With Ask Me Another, they send us the script for the episode and there's a ton of places where they want jokes. I'll spend hours writing, send them in, and then we all meet with the show’s host, Ophira [Eisenberg] for a read through. Then we go through the script and see what's working, do another rewrite. So many jokes. We all meet together once and we do two writing passes, basically.
The Side Ponytail team, who run a weekly comedy night at Friends & Lovers in the city. Photo provided by Emily Winter.
Ben: You were also one of the co-producers of the 2020 Brooklyn Comedy Festival. Well, what was to be the Brooklyn Comedy Festival, before everything got shut down. How long have you been with them?
Emily: I know one of the co-founders of the festival pretty well, he’s moved out to LA and is writing for television. Because he’s out there, they brought me on to help produce. So this was supposed to be my first year as co-producer, and I was really excited. And now it's not happening.
Ben: How much work had you put in already? What was the moment when you learned it was going to be canceled?
Emily: Let’s see. This year I was working on three special shows, shows that were put on by the festival itself. Then the rest of are already-existing shows in Brooklyn. So I had to reach out to all these producers, brainstorm good shows in Brooklyn, while other producers reached out to me. We had to decide which ones were good enough to make the festival, then they got their own lineups together. I also worked on getting the sponsorships and I mean, we were ready to go. We had a lot of promoting to do, but the bones were all there.
I was feeling we needed to cancel early on, before the founders. I didn’t want it to look like we needed to do this so badly that we would throw health concerns out the window. But then everything's shut down so doing the fest, that wasn't even an option. But I was actually the one pulling for “cancel, cancel, cancel,” because I don't want to be responsible if somebody gets sick.
Ben: Well if all the spreadsheets were done and all that I assume you already got paid, right? So maybe not the worst...
Emily: I didn't get paid. No money for me.
Ben: Ouch. OK let me pull this back from the darkness. With a lot of bands or DJs, the artists and their agents will impose radius clauses [limits on the number of performances in a given time/city] to reduce oversaturation. But I know a lot of comics tend to bounce around, doing multiple gigs a night...how does that work with a comedy festival when you’re trying to generate buzz for marquee acts? Do you have to limit appearances? How does the booking work?
Emily: Um, no. I totally understand what you're saying but with the Brooklyn Comedy Festival it’s a little bit different. We just kind of hit up the comics that we love. We're so entrenched in the comedy scene we don't really have to reach out to agents and managers. It’s more, “Hey, we're doing this show. This is our budget. Are you in?” And you don't have to be in if you don't want to be in. It was very casual. It’s just not the kind of the huge budget thing where we would be drawing up complex contracts. The purpose of the festival is to just showcase the best Brooklyn comedy that's already happening. It really does draw people's attention to comedy for a week. And that that's sort of the goal of the festival right now.
Ben: So it kind of has the vibe of say, Restaurant Week where there's all these existing spots, and you're helping focus PR and adding a few select marquee events.
Emily: Absolutely. Yeah.
Ben: Is there a plan to reschedule for later this year, or is it postponed till next year?
Emily: We're not sure at this point. It's so, it's just unknown. Everything is so unknown. I personally had a show that was supposed to happen at The Bell House this March and that's been rescheduled for July. I hope it happens. I mean that, that wasn't part or March that wasn't part of the festival. But. Um, it's, it's just, I think it's too much to really reschedule at this point when everything's still so up in the air.
Ben: Are you starting to see people who were previously hosting live nights doing their shows online? Are you going that route?
Emily: Yes, that's happening a lot. There's one comedian, Kate Willett, who's wonderful, and I think she's doing a show at the same time every night. It might be nightly or weekly, I’m not sure. But I have opted to stay out of it and just use this time to write. My husband and I are doing some creative writing together, also. I just finished another script. That's what I'm doing. I'm going to write my way out of this.