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Winstead tracks highs and lows of comedy game

JOE GROSS, Cox Newspapers

Publication: The Day

Published 06/25/2012 12:00 AM
Updated 06/24/2012 06:57 PM

It is a weird trick of show biz that you might know the folks whom comedian Lizz Winstead has made famous intentionally or otherwise better than you know her.

In 1996, a television program called "The Daily Show" premiered on Comedy Central. Winstead, a political and topical stand-up comedian since 1983, co-created it and served as head writer and correspondent until 1998, when she left after conflicts with then-host Craig Kilborn.

Kilborn left soon after and was replaced with a comedian named Jon Stewart (whom Winstead, coincidentally, knew from her time on one of his old shows). You know the rest.

A few years later, in 2003, Winstead co-created the progressive Air America Radio network.

One of her co-hosts on the program "Unfiltered" was Public Enemy frontman Chuck D, who was already pretty famous in another field.

The other co-host? A young journalist named Rachel Maddow.

But these things happen, and those are the things that make up Winstead's first book, "Lizz Free or Die."

It's not a memoir as much as a collection of essays reflecting on key moments in her career, the sort that shaped the way she looked at the world.

In an interview, Winstead said she's been thinking about the book for years, ever since she was first asked to write one around the time "The Daily Show" was taking off. But she was 35 and in the middle of running her dream program, which also happened to be her first, and the book would have to wait.

"Then in 2006, my father died," she said, "and a lot of stuff was laid out for me. There was a lot of looking back at what I had done up to that point."

Winstead grew up in Minnesota, the daughter of devout Catholics who lived within a block of her church and school, the better to keep her from the "Lutheran martial law" she says pervaded the community.

"My mom was from an insanely Catholic family and converted my dad from being a Baptist, but I think it was just so that she would have sex with him," she said.

In college at the University of Minnesota, Winstead haunted the rock clubs, especially the legendary First Avenue and its little brother Seventh Street Entry.

She saw endless sets by Hüsker Du (whose own Bob Mould later wrote the "Daily Show" theme), Rifle Sport, Soul Asylum and her beloved Replacements.

"I would have to say the Replacements were my favorites," Winstead said.

"It was that band that brought me to a lot of amazing relationships in my life, but also for their music and the community around it. I am glad that all of that (the early Minneapolis punk/indie scene) happened at a time when I had a lot of energy."

When she was 23, she started doing stand-up comedy. "Stand-up is a very strange form," she said, "and one of its craziest qualities is that you have to develop an act and confidence simultaneously."

Winstead said it took her about eight years to really find her comedic voice.

"Then I found I really liked responding to the world and to politics, so I worked that into my act for about four years," she said.

Moving into politics and topical comedy has its price.

"A lot of people go to a comedy club on a Friday night just because that is where they want to go," Winstead said. "When you talk about politics, you are automatically going to alienate 50 percent of your audience, then there's another third aren't interested in hearing about politics on their night out, so you have to build on that audience."

Then "The Daily Show" happened, a project of which she remains most proud.

"The program did exactly what it needed to do," Winstead said. "It wasn't launched as 'Anchorman.' It was satire and remains as such."

Air America was a different fish-kettle. The chapter in "Lizz Free" on that network is a laundry list of how to run (or not run) a company as cheaply as humanly possible (sharing offices with boiler-room stock traders, sweatshop-ish conditions).

"When you want to be a content provider, you have to spend more, and they just didn't," Winstead said.

After Winstead left Air America in 2005, she had a choice.

"After those two major projects, 'The Daily Show' and Air America, I realized that I really did miss performing," she said. "With those projects, I was writing up to the minute, something I used to do for myself and now was no longer doing."

These days, as she moves from stand-up gigs to theater productions to filling in for Sirius XM radio hosts to upcoming projects she can't quite talk about, Winstead remains committed to performance and commentary and satire.

"In writing these pieces, it reminded me that the ups and downs, the triumphs and then the falling back, don't matter that much as long as you stay in the game," Winstead said. "I know a lot of really talented people who quit too soon."

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