The Headliner: Maggie Winters
"It's so silly, too, how complicated the process is for, like, me posting a video that’s about diarrhea."
Maggie Winters, Comedian
The first time I visited Chicago, I was in my freshman year of college. Comedy was just starting to really become a ~thing~ for me, and I knew I had to see some iconic Chicago stylings while I was there. Unable to get tickets to a Second City show, I headed to the iO. I ended up seeing a drunk Shakespeare kind of show, but as I was leaving, I skimmed the show posters in the lobby, trying to take note of as many comic names and show concepts as I could. One name I saw? Maggie Winters.
Fast forward to this year, when a Maggie Winters Original came across my Insta feed. I instantly recognized her name — and I knew, as soon as I hit play, I would be in for a truly hilarious treat. That’s because Winters has a style all her own, combining personal humor with exaggerated modernity. I knew I had to have her voice in the newsletter, and thankfully, she agreed to chat with me. I had the pleasure of talking to Winters about being a Chicago comedian, creating comedy online, and living by Nike’s iconic slogan. Enjoy!
How would you describe your comedy?
It is such a funny question, because I feel like people will be like, “Your comedy’s like this.” … I just think “dumb” is what I would define myself as, but in a fun way. Like, I feel like things are so complicated that I'm like, let's just get dumb every once in a while. We don’t have to use our brains too much.
A lot of your comedy tends to be based on things that are happening in the news, or just real-life things. Is that what inspires your comedy the most, considering that idea of “let's take what's happening and make it dumb”?
I'm very impulsive. I have friends who are like, “I've been working on this video, and I'm gonna release it in two weeks.” And I'm coming home like, I'm recording now, and I'm sending it out now. … It's usually like, everyone's talking about it, so why not, if you can put your two cents in in a dumb way or a goofy way. Intelligent people are already saying, you know, what we need to hear.
Could you walk me through your path to comedy?
Like probably a lot of comedians, I, in grade school, was definitely bullied and then found … that, when I made people laugh, it made me feel so good, and I was like, oh, this is my in with people. Like, I'm tricking people. … Also, my family was just super into comedy. My mom loves SNL. She's the only person I know that watches it, like all—the next day, she watches it. Not, you know, not at midnight anymore, but she always watches SNL. And I have two older brothers who are very into comedy, and we would always watch, like, the Chris Farley and Adam Sandler movies. And I just remember being obsessed and being like—I kind of was like, … I want to be a Chris Farley. And then, from there, I kind of — like in high school — always wanted to act, so I did theater. I was a theater kid — sorry. You're like, “Stop the interview.”
I actually have to go. [laughs]
[I] just was always leaning towards comedy. I wanted to do improv in high school, and the theater teacher was like, “No, we're not doing improv.” And I was like, uhhh, okay. I minored in acting in college, because I was like—hot take, I don't think you need a degree fully in it to [do it]; it's more about talent, right? And then, after I graduated, I was like, okay, I'm from Chicago, and Chicago is such a hub for comedy. I'm going to start doing improv and go from there.
I did improv for a long time, and then, right before the pandemic, I took this class, FemCom, in Chicago, which is basically to get women to do stand up and nonbinary people to do stand up. So, I was like, let's do it. And then, the pandemic hit, and I was like, okay, and kind of missed that attention so transitioned to doing online stuff. And now I do stand up too; and improv still, sometimes; and online videos.
Do you have a preference between stand up and improv? I mean, obviously, you transitioned into stand up and did improv first, but I’m just curious if either passion outweighs the other.
When I'm doing more of … one, I will say the other one is what I prefer. I’ve been doing a lot of stand up the past couple years. I've been like, God, I miss doing improv. And now, sometimes when I do improv, I’m like, God, it's easier just to be on my own doing stand up. Doing improv is my first love, for sure; you don't have to go into it alone, you have a group of people supporting you. So, it's just, like, I find it way easier. Stand up is a little bit more cutthroat to me.
In the comedy world, people tend to look at LA and New York as comedy endgames, whereas Chicago is like the “train here and then move” city. What kept you in Chicago?
I am such an advocate of Chicago comedians, and I feel like, for a long time, we just g[o]t looked over. People will be like, “Oh, New York or LA.” And it's like, Chicago is a huge [hub]. A lot of people will be like, “Oh, you should start in Chicago, and then you should move,” … because of industry; we don't have a ton of industry here. I totally get that part of it. But just doing shows — like, I would say I do more shows than some of my LA friends. If you like performing live, it's an incredible spot for that.
In the past year, a lot of people are like, “When are you moving?” Like, that's their biggest question. Being from here, I'm super close to my family, so getting the opportunity to do comedy and be close to my family — it's the perfect mix. If I ever did have to move — fingers crossed, I get some cool job that I move for — … I would, but I think not having an industry here helps us a ton. Because, when I've done shows in LA or New York, people will be like, “You never know who's gonna pop up!” In Chicago, it’s like, no one’s popping up. It’s for the pure love. … And if someone did come, it would be insane, but [Chicago is] usually just to get practice, to get reps, to actually better your comedy. So, I think that's a big benefit.
You also started creating these online videos during the pandemic that are, essentially, small sketches. Had writing like that fed into your career at all before that time, or did that really start to factor in during the pandemic?
I wasn't really writing a ton. That's why I love improv, it’s—you just show up. It definitely was a goal of mine to start sitting down and writing more. So, I think, when that happened, it kind of forced me to do it. But I still say, with my videos, it's like half written or thought out and half straight-up improvised. The idea is they are [written], but then what actually comes out is improvised, so I still gotta push myself to write a little more.
From the comedians I’ve spoken to, I’d say that's pretty common — to only have half of the written work done — especially for people with improv backgrounds. Do you do that for your stand up as well?
When I first started, I was, like, so scared of stand up that I would do the thing you're not supposed to do, and I would memorize every single thing I was gonna say. So, it was very stiff when I got there. And I felt, and over the past two years, I just come up with the idea and then try to maybe riff a little bit. I feel pretty comfortable riffing if I have to, or if someone in the audience starts talking. I am distracted very easily, and I feel like I will comment on whatever is happening in front of me.
For people in the online comedy space, there’s this overwhelming urge to pander to algorithms instead of pandering to specific audiences, since success is based on views. What are your thoughts on that idea and what's happening generally in the digital comedy space?
It's so complicated. … I used to think about it as like, you're the artist, you create art, people come to you if they appreciate your art. In an ideal world, that's what you would do, but we're human, and we want to do well, and we want attention. So, sometimes it's like, okay, I'm going to do something that's on topic and what's happening in the world. So, that's pandering a little bit, because you're … not just doing something totally random.
But I have had times where I've gotten super like, I'm gonna make something that I want people to like. Always with me, the things that I think I’m gonna make [and people will like], they’re gonna hate it — or, not hate, but it doesn't do well. And then, the things that I just come up with, [and that] I'm like, whatever — that's what always does well. … It is something you have to work through, and it's not just one and done. And every time I make a video, I have to kind of work through that.
Also, in general, [there’s] getting over the cringe of it. … A lot of people will ask me, “Oh, how do you get into the online stuff?” And I'm like, you have to just get over the fact that you're posting. You're doing solo videos by yourself in your apartment for the world. You have to get over it if you want to do that. It's so silly, too, how complicated the process is for, like, me posting a video that’s about diarrhea. Like, this is so public.
I’m drawing a parallel here between the idea of having to get over the cringe aspect of posting stuff online and the implicit cringe of being someone who does improv or getting on stage and doing a stand up set. Do you think those things are similar at all?
I would definitely say it's similar. I think it’s probably a little more [cringey] than the live space. Because, with improv, once again, you're with all these other people. Stand up, too; you're never on a lineup alone. …
There's people posting videos nonstop, every day, all day, but … it feels very alone, secluded. You're like, I'm posting to the world! But then, I scroll through, and I'm like, 17 of my friends just did, too, so what am I—it just feels… you know what I mean? But definitely, because improv… [is cringe]. [both laugh] Come on, like, what? I'm having a blast up here. I don't care!
Something that interests me about online comedy is the feedback process. With stand up or improv, it’s immediate; you do something funny, and hopefully, people laugh. But with online stuff, you have to post it and then walk away to let it sit. What’s that like?
It's definitely harder. … I feel like I'm a very impatient person. So, when I post, sometimes, I’ll have to have these talks with myself. I'll post them, and it’ll be one minute later, and I'll be like, well, it didn't go viral. And it's, like, it's been one minute — calm down, slow down.
You have to kind of trust yourself. Like, for a while, I would have to be like, don't delete this immediately. If, in a day, you really feel strongly about deleting it, whatever, go off. But, in the moment, you have to let it breathe. Like, some people are fully at work. But then, eventually, you do get feedback. And it's weird, because it's feedback that you can read over and over. … It's so weird to see negative and also positive feedback. I just read some article — actually, I'm gonna sound so dumb, because I don't remember what it was or who — but they were like, “We're not meant to get this much feedback, negative or positive.” I was like, yes, I was like, I truly feel [that]. Especially on Twitter, I was feeling like I get stressed out when people would respond, even when it's not negative. I feel the need to respond also back, and it's like, oh, yeah, you're not supposed to get this much feedback. And I'm like, okay, that makes me feel better. It's like everyone's feeling this way.
What’s a joke or online bit you love that either never lands, lands really inconsistently, or just doesn’t hit those successful metrics online?
I feel like there are so many times this happens! I do think anything I usually really think will do well usually doesn’t, and anything I feel “ehh” about pops off. I’m always surprised.
Who are some of your influences, both in comedy and in life?
I mean, I have to say my two older brothers. Hate, hate saying it but have to say it. Barton, Liam — they're five and eight years older than me, but we're very close. And we just wrote a pilot together. And they, to me, are two of the funniest people. And just growing up, I always wanted to be funny like them. … And then, I mean, my parents too, my mom. I just make fun of her a lot, but she truly is—she is funny. …
In the comedy world, most of the people around me inspire me all the time. My friend, Parker Callahan — I don't know if you've ever seen his videos. Every time I see the things he created, I'm just like, this is—it's so intelligent, so good. …
But, one of my favorite people, I say, in comedy is Melissa McCarthy. Like, I think just as a plus size woman — I'm like, you know, shooting right for it — but it's, like, she went for it. And Chris Farley and Adam Sandler will always have a huge place in my heart. …. And Rachel Dratch, and Maya Rudolph, I mean, Tina Fey, and Amy — all the SNL people.
I love Patti Harrison. I got to meet her in person, and it was one of the craziest moments, because we walked into this really tiny bathroom, and I was like—I kind of jammed the door. And I was like, oh, sorry. Like, this bathroom was so small. And immediately, she goes, “I designed the bathroom.” I was like, Patti you—like, on immediately, just funny. Like, of course you'd have this joke just ready to go.
Okay, at this point, I have to ask: Do you have a favorite era of SNL?
I mean, just because of the people, like the Chris Farley, Adam Sandler years. … My favorite sketch in the entire world is the decaf coffee Colombian crystals [a Hidden Camera Commercials sketch]. I think about that all the time; it's so good. Like, [Farley] just gets so raging mad and flips the table, and I'm like, that's heaven to me.
Is there anything else you want to say about your career or comedy overall?
I think the biggest thing when I think about comedy is, like, I think about the phrase just do—I was gonna say, “just do it.” [laughs] I really meant, like, do the thing. People always are like, “How do you get into it?” It’s, like, it's so annoying. You have to just constantly do it, and it's constantly scary, and annoying, and you're tired. But then, every time I look back, I'm like, wow. … That's just my biggest thing, is, like, you gotta just do it. Nike, baby.
I can't believe I was like, I'm gonna say, “just do it.”
You’re like, “I just have to say, ‘just do it’ every time.”
I'm actually sponsored by Nike, so I have to say that legally at the end of all interviews.
I'll put “paid sponsor” at the bottom [of the interview].
[both laugh] Honey, I wish I had a paid sponsorship.
You can see more of Winters’ genius on Instagram and Twitter. Follow to stay up-to-date with all shows, events, and just general comedy chaos.
This interview has been edited and condensed for clarity.
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