Lizz Winstead and the catharsis of comedy in troubled times

Jim Lundstrom

I had no idea when I had arranged to talk to Lizz Winstead that she is a rabid Minnesotan. I knew she was born and raised in Minneapolis, but I figured, being a Leo of the generally same age as me, she, too, could not wait to leave staid and steady Minnesota when she was able.

“You know, it was weird, because Minneapolis, I think, was a little different,” she said. “Growing up in it, you know, coming of age in the ‘80s, the music scene was great, the comedy scene was great. And so, in figuring out what I wanted to do, I could develop creatively in a way that I don’t think you could do in most other cities.”

She feels Minneapolis at that time was unique for an aspiring creative.

“There were a lot of folks who grew up someplace else and wanted to be a musician or comedian or something, they would have to go to one of the coasts, and then try to break in,” Lizz said. “And sometimes that can kill you, because some agent walks in and sees you young in your career, you have a bad set, it can kill you, right. And so for me, it was so great to be able to be here. Comedians came through town, and I could develop my act. I mean, I could be on stage every single night and work my restaurant job in the day. I worked at Grandma’s, by the way, when it was in the Twin Cities. So, when I was ready to go, I think part of it was that I had to move on to the next step and try that, you know, figure out how I could make it because the one thing that Twin Cities wasn’t really doing was producing TV shows, right?

“So I grew as a comic here, I made connections here,” Lizz continued. “I also love it here, and so I feel like I didn’t have to run away. I just had to get to the next level. But I always have come back here. I never went like oh, I moved away. I would come back here for a month in the summer. For my whole life I’ve come back the whole month of December. So I really revered Minnesota to the point now where last year, I finally bought a place here. So now I live in Brooklyn, and in the Twin Cities both. I split my time.”

Lizz attributes her drive to do stand-up comedy from “being the youngest of five kids from a Catholic family and never getting a word in edgewise. It’s like, oh, a stage is where I get to talk, and nobody else does. Maybe that’s a good place. Because I had thought of the priesthood, and then I realized that I was not invited to that club.”

Fear and adrenaline got her through her first stand-up routine at a comedy club.

“Second time I bombed. Third time I did OK,” she said. “Then I had to try the fourth time to figure out what’s going on here. And then I just keep trying it.”

Her mission in comedy was to say the things people were not saying, and that meant politics. It also meant overcoming two strikes as a comedian – having political opinions and being a woman in the boys’ club of comedy.

Did political humor affect where she played?

“Oh, 100%,” she said. “I lost audience members. There were clubs that were like, Yeah, I don’t like your politics, so you won’t play here anymore. People often say, do you feel like it’s polarizing because you chose to do politics or put your opinions out there. Everything’s polarizing. There’s people who don’t like babies. And there’s people who don’t like chocolate. So I mean, just having an opinion is polarizing, and being a woman and doing stand up is polarizing. There were places that no matter what I talked about, they wouldn’t book me or if I got booked, it would be with all women on some kind of freak show night, you know, because only women would want to see women, you know, it’s like, do men want to hear what women have to say?

“So I realized that once you started having opinions about things, or wanted to share your point of view, that you needed to find your audience. So I would flyer in neighborhoods where people would be more like-minded, at coffee shops, community radio. I would just find places where I was building an audience.”

And with that she a saw a career path for herself as a touring stand-up comedian.

“But I was always open to opportunities. So when an opportunity arose to write on a Comedy Central show called Women Allowed, I was like, Oh, I can be a writer and a comedian. And then I didn’t know if I would like that,” she said. “But the second the words that I wrote came out of somebody else’s mouth and they got a laugh, I felt the same satisfaction as if I was saying it myself. And so that was a pretty cool thing to realize, that I could open up another avenue for myself that I didn’t always have to be the messenger. You know, it was fun just to hear stuff that you thought was funny, somebody else that was funny, and then have that come out of their mouth too. So I think I just followed the path of opportunity and kept myself open. So I love writing. I love performing. I love activism. And I think I just had to weave my way through, to not silo those things out, but to eventually create a place where I could speak my mind on how I felt about the world about politics. Do it through a comedic lens, you know, basically crap on bad guys for money. How am I going to do that? And I just kept figuring out ways to do it. I kind of did it through my stand up, and through a little bit of writing for a while. And then because my stand-up became more political, I got approached to help create The Daily Show. That was sort of the beginning of me really being able to hone all those things together.”

The Daily Show premiered on Comedy Central on July 22, 1996, with host Craig Kilbourn, who had previously been a sports anchor at ESPN. It was meant as a replacement for Bill Maher’s Politically Incorrect, which had moved to ABC.

Lizz created the show with Madeleine Smithberg.

“It’s being able to combine the hypocrisy of the powerful with comedy,” Lizz said. “That’s what was to me. In my observations, always, it wasn’t just the politicians and the corporations and the greedy people we need to target. It was always a lazy media that didn’t hold them accountable because they gave them platforms. And so one of the things I think I’m most proud of is, what we did on The Daily Show was to create a whole structure that looked like them, but was holding them accountable at the same time. And that was pretty fun. And it was also the place where I really feel like, the only thing you kind of have in this world is your instinct, right? It’s kind of like, if my instinct tells me to go with this joke, or these people or this thing, I can count on it. And my instincts in creating the format for the show, choosing the correspondents, the writers, and watching it all come to be was really self-esteem boosting for being able to move forward and take on controversial topics and do things that were going to be a little bit more off the beaten path.

“Working at The Daily Show, and creating that was sort of like the early days of SNL. Nothing had been like this before. So all the topics were your oyster, all the things where you could do anything, because you didn’t have to say, oh, that show is already doing that, or that show already did that? Because no one had done it before. So that felt incredibly exciting.”

While still at The Daily Show, Lizz got a call from Al Franken, who in 2004 was helping to start Air America Radio, providing progressive voices to counter right-wing radio.

“Al Franken called me and said, ‘We’re looking for a Lizz Winstead-type to run the network,” Lizz said. “And I was like, a Lizz Winstead-type? What about me?”

Franken told her he had assumed that she would not want to leave TV for radio.

“And I said, ‘Are you saying that you’re giving me an opportunity to program 18 hours of progressive radio and do what I do in a medium that is so personal.’ He goes, ‘Well, when you put it that way’.”

She said it was an exciting time getting to know a new medium and hiring folks for the network.

“It was really exciting to be able to be the program director there. And so I was able to choose Rachel Maddow, and Marc Maron and Chuck D.

“Nobody trained me to be a TV producer, nobody trained me to be a radio programmer, I just did it on my own and made some bad mistakes, made some good decisions,” Lizz continued. “Everything was self taught, it was crazy, that it actually worked. And being a woman doing it, you know. You look at my resume, and for a lot of years you wouldn’t see a woman with those kinds of credits. And I feel pretty proud of that, to be able to bring women along the journey.”

Had to ask if she had a favorite Daily Show moment from her tenure.

“Oh, wow, that is tricky. I would say favorite standout moment was, this is gonna be silly, but we were doing the political debates in Hartford. It was the Republican debates. After the debates there’s what they call Spin Alley. Each network has an area where the politicians come to be interviewed. You’re up on a little riser. John McCain was talking to us, and he was moving. And he fell off the riser. And he just kept talking. And then he just came back up on the riser. So nothing had happened. And it was hilarious. Yeah, he fell off, got up and just kept on. Like, wow, that was amazing.”

Lizz said she hasn’t done a show in Duluth for years, so looks forward to the Sept. 15 show at the West Theatre. That title of the show is “Everything’s Awful.”

Is it? I ask.

“You know, I think in general it can seem that way,” she said. “If we really thought everything was awful, would we be laughing? Probably not. But I do think that I do bring perspective to the awful and to bring humor to the awful. I always say, when the insurrection happened, why don’t we send in those moms who jog with their dogs and strollers because they have a steely determination that would break through any group of asshole men.

“So I think that finding humor in our own power when it feels like we’re powerless, and reminding ourselves of that is important. And I do think that we’ve seen a bridge too far. I think the overturning of Roe woke people up in a way that reproductive rights never has, even amongst Democrats and, you know, progressives. So it’s nice to be able to have people see a lot of the things that are happening and you know, you don’t want to fuck with women, it is a bad idea. There is a breaking point. And I am sorry for the wrath that we are about to bring down upon you.

“So I think that the world right now is something that is a mess. And if we can’t examine it, and figure out where the humor lies, I think that that’s the death knell. I’ve always said if I can make people laugh, it means they still have hope. Because you’re tapping into an emotion that’s involuntary and also brings joy. So if you can feel that joy, and you’re in a group of people who are also needing to feel some joy, I think it’s good when you can gather as many people together to talk about the state of things in a way that’s funny so that you can see community around you.”

Of course she has been asked if she isn’t preaching to the choir.

“Does a choir have one set of songs?” she said. “I feel like there’s many songs of choir can have. And you don’t walk into a butcher shop and say, Why do you only sell meat? I’m selling a product that people want. If somebody’s like, ‘Oh, I hate politics. I don’t want to go, I won’t think it’s funny.’ Then they won’t waste their money that night. You know what I mean? So I’m like, as loud as I can be trying to get the people who feel like they need a catharsis to come. And then also to save those people who would rather spend their money on MAGA hats to just do that.”