The Laughspin interview with Lizz Winstead

If Jon Stewart could be called the Ben Franklin of modern American satire, Lizz Winstead is certainly its Betsy Ross. Okay, sure, it’s been a little while here since ninth grade Civics class, but see if you can’t follow the logic train: while Stewart may be responsible for ushering in a new era of brilliantly barbed politic-wit – at this point, he’s probably dropped enough knowledge to fill several more Poor Richard volumes – the venerable Winstead is the lady responsible for stitching together what would prove the origins of truthiness’s vividly high-flying flag.

As The Daily Show’s creator and cardinal head writer (fitting, as she once entertained childhood notions of entering the priesthood), we have Winstead to thank for laying the groundwork out on a comedy show that eventually went on to become a longstanding symbol of satirical perfection. The Daily Show – and by extension, it’s sister spinoff Colbert Report – is arguably as influential and culturally important as, say, Saturday Night Live or Johnny Carson’s incarnation of The Tonight Show. And at this incredible genesis, there is Lizz.

But Winstead didn’t simply birth a work of genius and then set her sewing needle back into the haystack. An accomplished comedy writer and stand-up performer in her own right, she has continued to operate as a prominent voice in the fight for social justice causes the nation over. Her first book, the hilarious, poignant memoir Lizz Free or Die (available here) paints an elaborate portrait of an observant, authentically funny lady whose background forged a direct pathway into the fascinating life she leads at present. From her harrowing experience with an unplanned teenage pregnancy to the trials and tribulations of dog ownership (shit-eating dog ownership, at that), Lizz has a lot to say – every word of it as captivating, introspective and, naturally, gut-busting as the woman herself. Let us all now agree to let Lizz allow her freak flag to fly, for we are all the better because of it. Who would dare tread upon it?

Let’s jump right in and start chatting about the book. One thing that caught my attention early on was a term from the earlier chapters regarding your childhood – you call yourself an “unlady,” meaning that you were frequently accused of engaging in unladylike behavior. Do you think these experiences were integral in developing the larger role you currently play in advocating for women’s rights?
You know, I think that… yeah! It wasn’t really a calculated thing; I have this thing called the “anvil rule.” I can’t lift an anvil, so if I tried to lift an anvil, that would be dumb of me. So anything that doesn’t involve me lifting an anvil – if you were just to say no to me for any other reason than that – then I was very suspect of you. It’s like when I wanted to be an altar boy: there was only one thing preventing me from doing that, and that was that I didn’t have a penis. There was no heavy lifting.

It came to the point when I was older where I just wasn’t interested in these preconceived notions, like what society wanted me to be. To me, having a kid is like lifting an anvil, in the sense that I’m not good at that. People say of motherhood that it is the hardest job in the world, then I should be the one who decides whether I’m able to do that or not. [That decision] shouldn’t be made by somebody else; we want good mothers, right? And I think that’s why I gravitated toward social justice issues – if two people of the same sex want to have a relationship, that’s not an anvil, that’s just two people wanting to have a relationship. You’re going to stop someone from doing something that comes naturally just because it’s different? That’s so weird to me. It’s a lot easier to call people out on their bullshit when there’s no anvil involved.

I also think that lead directly into the whole reproductive health thing, especially with my preexisting views on how hard motherhood seemed. I just don’t feel like I have the DNA to carry out what that job entails. Why should I be forced to do it? You mean I just shouldn’t have sex? That’s crazy!

That’s one thing I definitely connected with on a personal level in the book: your described disconnect from babies. That’s a feeling I’ve always identified with myself. Tell me, does the stigma get any easier? Do people eventually stop looking at you with dismay when you say you have no desire to have children?
Oh, you should read this: this guy wrote this blog post about me, all about how I hate motherhood; how clearly, because I had an abortion, I’m trying to justify it by making motherhood a bad thing; and just all this craziness. There is a stigma attached to it, and people try to put it on me, but it just rolls off of me because a) anybody who knows me knows I wouldn’t also choose to be a racecar driver or a neurosurgeon or any job that’s really hard in that way. I do not feel that I am somebody who could that. Once you make this realization, it’s a lot easier to deal with all the haters. It’s not as though I’m an uninspired person, who didn’t want to pursue difficult or challenging things – I just chose to pursue things that I thought maybe I could be good at and put out for the world that other people could enjoy. If I could raise really smart and interesting kids, who would go out and make the world a better place, I would have done that. But I don’t think I have the wherewithal to do that.

In some ways you could say that your long career in developing game changing TV shows is like your children by proxy. But it’s almost better because it’s a legacy that lasts longer, you know what I mean?
Uh-huh. It’s a legacy that exists for a lot of different people. It has morphed into other things, which maybe no longer have anything to do with me, but that’s fine. To me, my personal legacy isn’t really as interesting as something that I can show off to the world and that other people can take on and make it their own, other people can make it their own, and so on. It makes something that’s bigger and more amazing than the initial kernel of what it was. That to me is something that comes from having a good idea.

Let’s talk about that chapter in your book where you describe going to the crisis pregnancy center. You were expecting it to be an abortion clinic, but got slut-shamed instead – something that’s probably happened to hundreds, if not thousands, of women around the country. You do kind of allude to the fact that you did end up getting an abortion later on in the book, but I’m curious to know how you finally ended up getting the resources that you needed.
Here’s what’s so crazy: I saw the advertisement on the city bus for this crisis center, and of course they mask everything in language that’s meant to manipulate you. So it said “pregnancy tests, choices, options,” so I went there, and it turned out to be this horrible place. I left there, after that woman had made me feel like a criminal, and I got back on the bus, and sat on the other side of the bus this time, and there was an ad for Planned Parenthood! It was like, oh my god, if I had just sat on the other side of the bus, I could have just seen that and been done with it.

On some level, I’m kind of glad that happened to me, though. It helped me learn about those predatory places that are out there. I had to sit down with a counselor who asked me question about my life choices and what I was doing, and it made me stronger in my resolve, that I’d made the right choice, which was to terminate the pregnancy. So I’m glad I went through this. Somewhere down the line, I’ve expressed to people that this is something a lot of people go through. People go through this all the time; it’s not uncommon, and it can help form the thought process that takes you to a bad place, because somebody is demonizing you. So I wanted to shed a little bit of light on [the fact that] these places are out there, and they prey on women, and they are unregulated, and they get to tell you a whole bunch of things that aren’t true, and nobody stops them.

Moving on to your career in general here, when you’re combining politics with comedy on any given media platform – be it your Air America radio show or as a guest on a talk show – is it more important for you, as someone so deeply involved with these heady issues, to have your point made, or to be funny and entertaining? Do you choose one if you can’t find common ground?
Sometimes I just get so frustrated with it, I’m like, blah. [Laughs]. But I try to craft my material in a way that uses and points out the hypocrisy of an issue, so that people can think about it and talk about it more. So it’s not necessarily about proving a point; a lot of times, it’s about asking a question, you know? “Does it seem like a good plan, that you want to reduce the level of abortions by removing all access to birth control?” I like to give people something to chew on and think about further. Also, that ties in to making them laugh, because if I present something in a funny way, it helps override this crazy rhetoric that’s coming from the right.

One thing I really liked in the book was this creative tactic you have where you combine two words to form one new thought.
You mean where I make up my own words?

Yeah. My favorite one, I think, was “awkfidence.” When did you first realize that maybe this was a comedic asset for you? Is this something you’ve always done?
I’ve always tried to create funny words and phrases. Some are easier to figure, like “crackpottery,” but my favorite one, I think, is “anticipointment.” I don’t know if I put that one in the book or not, but basically, the key to “anticipointment” is something like “check out George Clooney in a hot tub with who?” And then you find out that it’s a non-story; a really disappointing scenario. It’s like man, you got me all excited.

So yeah, I think I do like to make up words, and I’ve kind of always done it. It’s a fun little thing.

In the book, you also describe this alternative comedy scene that was sort of happening concurrently to the alternative music scene unfolding in Minneapolis in the late ‘80s. Of course, bands like Husker Du and The Replacements are now household names, so my question to you, then, is why do you think that those responsible for the musical aspects of such a movement get more credit for shaking up the zeitgeist than the comedy elements do?
I would say that we didn’t even really consider ourselves alternative comedians. We were just comedians. And the music scene was just the music scene. We knew that we were weird, and we knew that we weren’t the mainstream, but we didn’t think we were the alternative to anything else. We thought that we were, um, this crazy group of people who all found each other. When you think of people like Joel Hodgson and the Mystery Science Theater team, that’s probably the truest definition of alternative comedy nerd-dom, in this sense. Obviously, we didn’t have a lot of college radio play, so these bands totally made it in our town based on promotions from record stores and amazing music venues.

As far as the comedians go, that’s a really good question. I don’t really know. Maybe it’s harder to pigeonhole what we do. Audiences back then didn’t have the same access to our work as they do now, so maybe it was harder to showcase us at the time. What we did was relatively unique, so it was perhaps harder to get bookings outside of Minneapolis, whereas with music you have alternative music venues all across the country. The modern comedy venue as we know it now didn’t really exist up until about eight years ago.

I definitely laughed out loud at work while I was reading your story about the curtain pulling off your skirt while you were performing one of your earliest shows, leaving you utterly exposed in a way few comedians ever are.
It was probably the most amazing wardrobe malfunction in the history of wardrobe malfunctions.

What was going through your head right after that first happened? Were you tempted to run off stage, or did you immediately snap into comedian mode?
Well, here’s the thing. What was so fascinating is that I didn’t have the option to run off stage. I was trapped; I was hanging. I couldn’t run off stage, but if I hadn’t been trapped or hanging by the curtain rod, I might have run off stage. It could have ruined my life, in some horrific way. I could have been fired from the club, if I didn’t have the courage to go back out onstage. I didn’t have those options, so I had to take that moment and say, “I can either leave people with my vagina, or I can just own this moment, and see what I can make of it.” So for some reason, and I couldn’t even tell you why, I was determined that this wasn’t going to be the last thing that people remembered of me. They could remember it about me, but it couldn’t be the last thing they remembered of me. I felt like I was Carrie at the prom, so I was like, well, at least a bucket of pig’s blood didn’t fall on me.

The audience started laughing at the jokes instead of me and my vagina hanging there, and I heard a guy in the audience say “I think she planned this.” Yes, you know what, yes. Tell everyone that I planned this. Lizz Winstead is such a crazy performance artist that she’ll do anything for a laugh. Yes, yes, let’s go with that.

So I felt this confidence, once the laughter changed from nervous, oh my god, her freaking vagina is starring me in the face, to oh my god, this woman is fucking hilarious, and I’m laughing with her instead of just at her. Experiencing that profound humiliation gave me the confidence that maybe a life time of trying to do standup couldn’t have given me, you know what I mean?

Right. And I’m sure it’s crossed your mind since then that it’s a pretty good thing this didn’t happen in the age of cell phones and all sorts of video recording devices.
You’re telling me! I wouldn’t have had the luxury of being able to define it. Who knows if they would have kept the video going with me telling the jokes and making people laugh. Instead, I got to control it. The people [in the audience] were doing my bidding, rather than me being beholden to a bunch of strangers, putting it up on Facebook and stuff.

Speaking of you controlling things, let’s talk about your influence on Comedy Central a bit. You were pretty directly involved with curating some of the early talent and ideas there. What do you think has been your legacy to what has arguably become a pop cultural institution?
Well personally I would say that I’m not sure I can be associated with the voice on Comedy Central, because that seems giant. And I wish I could say that oh hey, look at all I did, but I can’t. The legacy for me was… we established the framework for The Daily Show. What we established was a following of the news cycle, based on a morbid curiosity with it, and pointing out the hypocrisy of picking your targets, as in just going after the big guys but not the little guys. We started doing that with a media that is much different than the media is now.

Then, when Jon and his team came in, they really took that, you know, skeleton and then made it into this super human. So I’m very proud that the skeleton was able to exist so that someone so talented, like him, could take it and create this, you know, force that’s larger than life. With the way they’ve spun it and the way they’ve developed it and the way they’ve made it evolve into this amazing thing – that part has been really, really great. They are really amazing to watch, and I love that I can be a fan of the show and watch it, and it’s grown to such a place that I don’t have any hesitation going “wow, Jon and his team have made this into an incredibly brave thing.” It’s really about the voice of this new generation of people that have developed it over the years.

Also from the book, you speak pretty frankly about the fact that you hadn’t really seen any young women performing standup, and you indicated that you thought it was potentially something that could hold you back. Given that you now hold a position that’s certainly radically different than when you first started out, do you feel any kind of responsibility to change the national dialogue on women in comedy?
I think that the best way that I can change the national dialogue on women in comedy is a), trying to be as good as I can be, and b), recognizing all the women who are making incredible contributions. I did an off-Broadway show called Wake Up World that ran for two and a half years, and the staff was stacked with [female] talent, because they were all really great. For me, the best reminder is to be in the game and to check back on the parts of the industry that might seem a little boys clubby still. It’s really important to do that, because there will always be institutions that aren’t that female friendly. You have to create your own atmosphere so that you can stand out, no matter what other people are doing with it.

Lizz, I need you to reassure me, I’m getting kind of scared: who’s going to win the war on women?

Women are going to win the war on women, and you know what? Living in the current age we live in… if this were 10 years ago, and we didn’t have Twitter and Facebook, all this anti-woman legislation and bullshit would probably not be in the forefront of the psyche of women. When you start fucking with our lives, they don’t seem to understand that our lives and what’s going on in the country are inextricably linked. A lot of that is celebrating being sexual beings and being able to choose to be parents ore never be parents. When that gets put under attack by people who don’t know us, women are gonna fight back. They’re not having it. They’re not.

So, in honor of the book title, Lizz Free or Die, can you name for me the moment in your life when you first truly felt free?
Hmm. Well, I think it’s a process, trying to find your freedom in life, because there are always people trying to have a say in the state of what you’re going to do. I would say the first moment that I felt free… it’s a great question, and I don’t know if I have an answer to that one. But maybe part of it was when I could get birth control pills, and I could explore my sexual self with safety.

For more info on Lizz, check out To buy her, book, go to IndieBound.

Emma Kat Richardson

Emma Kat Richardson is a Detroit native and freelance writer living in Austin, Texas. Her work has appeared in, Bitch, Alternative Press, Real Detroit Weekly, 944, and She’s enough of a comedy nerd and cat lady to have named her Maine Coon Michael Ian Cat. Follow her on twitter: @emmakat.

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