Lizz Winstead, Freely Speaking

Writer and comedienne Lizz Winstead did a lot for comedy and womankind even before she got the bright idea to co-create The Daily Show. In her literary debut, Lizz Free or Die (Gotham Books), she finally takes the time to share the truth about what is was like fighting to spark revolutions in television and radio. From The Daily Show‘s infancy to her darkest days relentlessly trying to build Air America with integrity, her collection of essays tells a story as only Lizz Winstead can.

We chatted with Winstead about sticking out, standing up, and fighting for sanity in a society that has lost its mind.

LIANNE STOKES: With all you’ve accomplished, what took you so long to decide to write this book?

LIZZ WINSTEAD: My editor approached me after the first year at The Daily Show. I said, “I don’t have a book in me.” Once a year for 15 years, he would call me, and I kept telling him no. After my father died, I started to reevaluate and thought, “Maybe I do have something to share.”

STOKES: What about your dad’s passing sparked you?

WINSTEAD: Truth be told, when you start your career out as a clown, you don’t consider yourself a writer. I had self-doubt about whether my story was interesting to people. I didn’t want to write something that was anecdotal. It was important to me that people would get something out of my book. I want people to read it and say, “Now I don’t feel so alone,” or “I’m going to remember that next time I’m being an asshole.”

STOKES: In that case, you’re doing God’s work. We are at max capacity with assholes.

WINSTEAD: [laughs]

STOKES: You’re the youngest of five kids. In your first chapter you divulge that you never had the “mommy gene.” This is something that many women don’t have the balls to admit. Society puts this pressure on women to the point that if we say we don’t want children it makes us fear appearing cold, selfish or unlikable. What did your parents make of you?

WINSTEAD: Well, my dad was a bit of a rogue.

STOKES: From what I can tell from the book, you get your humor and your courage from your dad.

WINSTEAD: I think you’re right. In an odd way, my parents were proud of me.  When they saw me do stand-up, I’d see them looking around the room and watch them taking in the people laughing. On some level, that comforted them.

STOKES: You became the first head writer at The Daily Show, and you had never managed or been on a writing staff before.

WINSTEAD: I hired a bunch of passionate, brilliant, ideological misfits, and none of them had ever been on a writing staff either.

STOKES: And The Daily Show was born.

WINSTEAD: The beginning, that’s the one story that only a couple people can really tell. That weird, crazy time was invaluable to what it has now become. Jon Stewart has taken it to this place that is so magical. It’s really fun to be a fan. I feel like I can say I’m a fan, because I’ve been away from it for so long. When the show launched, the state of the media was so awful. All we heard about was baby-shaking nannies, the Menendez brothers, and Heidi Fleiss. Our plan was to mirror the media that we were given.

STOKES: At The Daily Show, you’d receive phone calls from executives at Comedy Central telling you they wouldn’t run a joke you had written because it was too mean. Then you realized it was a simple adjustment that took your idea from nasty to smart.

WINSTEAD: Yes, think about it. When subjects, corporate people or whoever they are, have had years of getting a pass for being corrupt assholes, and you’re finally given the opportunity to take them on or satirize them, your first instinct is to say the most shocking thing about them that you can. And because it’s shocking, you laugh. Then you realize that you’re not being funny or satirical, you’re just being mean. People understand these guys are jerks. That’s why we’re making fun of them in the first place.

STOKES: What do you feel the difference between snark and really good satire is?

WINSTEAD: Snark stops the conversation, and satire keeps it going. If you’re just saying, “Sarah Palin is dumb,” that’s easy. What else are you saying? Good satire hopefully provides thought-provoking conversation. When you’re cruel, you shut the conversation down. Write a smart joke and people want to talk about it and keep the dialogue going. Also, if you can make someone laugh, it’s a pronouncement that they like you on some level.

STOKES: You hired Stephen Colbert as a correspondent. How did you discover him?

WINSTEAD: I’d been a fan of his work on Exit 57 and Strangers with Candy. Then I saw him doing these segments on Good Morning America where I saw him getting away with so much more than people were realizing. It clicked; this guy can do this. I didn’t make that connection from watching him on those other shows.

STOKES: I’m not going to spoil my favorite part of your book for readers because it’s just too good. But I’ll give a sneak peek. The joke your dad played on you and your siblings on his deathbed was legendary. He trumped you with that one, postmortem too!

WINSTEAD: He knew he was dying and planned it. My mother was in on it too. My dad is a great man.

STOKES: I like how you just said “is” and not “was”—he is a great man.

WINSTEAD: Yes. My mom’s a character, too. When I first brought Brian Unger, my boyfriend at the time, home, my mom saw that as an opportunity to plunk down a bottle of Beano on the table for me. It was right in front of him. Know what Beano is?

STOKES: [laughs] The anti-gas medication?


STOKES: Let’s talk Planned Parenthood.

WINSTEAD: You know that I went on tour for them, right?

STOKES: Yes. I’m a big supporter of Planned Parenthood. I signed every online petition I could in the last few months and donated money.

WINSTEAD: Good. At every Planned Parenthood stop, I asked each director if the attack on women has ever been this bad. Every one of them told me no. They have never seen it like this.

STOKES: Why do you think it is?

WINSTEAD: It’s the death rattle of the elderly, conservative, white male. It’s their last chance at oppression.

STOKES: That’s really interesting. When you said that, Newt Gingrich’s face popped into my head. That’s not something I want to happen again.

WINSTEAD: Yeah, neither do I.