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How A 'Daily Show' Writer Grew Up Funny

Lizz Winstead is a co-creator and former head writer of <em>The Daily Show</em> and one of the founders of Air America Radio.
Mindy Tucker
Courtesy Riverhead
Lizz Winstead is a co-creator and former head writer of The Daily Show and one of the founders of Air America Radio.

Lizz Winstead has always looked at life a little differently. She never believed that stork story, for example. She says she loved her Barbie doll when she was a little girl, growing up in Minnesota, but Barbie didn't mean impossibly perfect pulchritudinous plastic beauty to young Lizz. It meant something different.

In Lizz Free or Die, a new book of essays, she takes readers through the different chapters of her life: growing up, becoming a comic, helping to create The Daily Show, which has gone on to be a huge success (albeit mostly after she left), and Air America, which she loved, but fell apart.

Interview Highlights

How she discovered she was funny

"It's genetic in my family. My father is from Mississippi and a long line of storytellers. All of my siblings are incredibly gifted at telling stories. And I think I wasn't really like a goofball or didn't really tell jokes as a kid. I think more in high school did I realize, if I can crack wise, I can get away with some stuff. It's easier to be funny than it is to be angry. Because there's this interesting thing — if you make someone laugh, you have a bond. And so if you can make someone laugh who you disagree with, they have to acknowledge that on some level they like you, and sometimes then you can work things out."

On working at The Daily Show

"We were in a place where the news was so out of control at the time, in a different way than I might characterize it now. It was very tabloidy. It was very trial-of-the-century-of-the-week, and they could find any three weird oddities and create it as a trend to scare people. 'Dental floss might strangle your baby!' You know, just crazy pieces that were on all the time. We wanted to combat it so badly that I think oftentimes I would go for the jugular rather than the joke."

On going to the prom

"I was stood up for my own high school prom by a lovingly delightful hockey player with a mullet. And he stood me up for my prom as I was there in my dress and my corsage and mortified.

"He decided to go with another girl, so no prom for me. A little bit of a sore spot. Cut to age 35, and this sweet young fan of the show — he was, like, the first audience member to ever come to the show — he was, like, the first person in line. He had watched the show for about a year and become a superfan, and he would occasionally write me notes: 'I really love this joke!' And he really got nuanced, and he was that great nerdy kid that you go, 'Oh I wish you could see yourself in 10 years because you're going to be so excited!'

"So when it came time for his prom, he asked me to prom. And I was like, 'How can I not go?' So I said, 'Yes, I will absolutely go,' and we'll film the show. So I wore this inappropriate red dress. It was one of those, like, built-for-sin dresses, so that all these jocks would be jealous of him. And so we went to the prom and I decided that I was going to have a prom experience. We could've just shot the little pieces we wanted for the show, but I sat with the dinner, and I danced to 'Rock Lobster,' and he kissed me on the cheek, and then he requested a song called 'Lady in Red,' and we slow-danced to it. It was absolutely a delightful evening because he was such a great kid, and he was really fun."

On her father's last "dielarious" days

"Yes, dielarious: laughing with or at the expense of someone who is dying. And it is a word that I didn't ever use until my father passed away. My father was this amazing, funny southern storyteller. And our politics were diametrically opposed. He was a staunch Reagan Republican and I'm a crazy liberal. And we found this fun detente where we would both watch Jeopardy! together, because if we both could answer 'What is the Sudetenland?' at the same time then we couldn't call each other dumb.

"He always said to me, he said, 'You know, I raised you kids to have an opinion, and I forgot to tell you it was supposed to be mine.' "

On her mother

"She was never overtly critical. She was very Minnesota-backhanded critical, but she always did support me in a way that was pretty incredible. She would defend me to the death — take my pictures when I was on the TV, because they didn't have a VCR. And then show those pictures or cut out clippings when I was in the paper.

"I grew up with conservative parents in a very progressive community in Minneapolis. And so a lot of her friends were Democrats, which, you know, she would say things to me in her later years in retirement, and say, 'Well, you know, sometimes at my dinner table at the retirement home, they sit me with the Democrats. And I've said I'd rather sit with the Alzheimer's people.' So yeah, she was quite a character in her own right. Very different sensibility than my dad. But you know it was again, just lucky to have these gifts from these parents who reiterated how much humor was part of us and how important it was to keep it going. And now I feel like I have a legacy that I'm carrying on."

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