The life of Lizz Winstead

Winstead has missed the state fair only three times

Winstead has missed the state fair only three times

It's a Saturday afternoon at Café Maude, and Lizz Winstead is discussing the finer points of a Bloody Mary with a waitress.

"All you need to spice it up is horseradish, Worcestershire, and a little pickle juice," Winstead says in her characteristic brassy voice. "But people will put the red pepper vodka in and think they're doing you a favor."

The waitress agrees, then adds, "I just saw you on Rachel Maddow."

Winstead's strong opinions aren't limited to breakfast cocktails. The iPhone on her right is slapped with an anti-mining sticker, and as she talks, her hands brush aside a thick scarf to reveal a red fabric "A" pinned to her sweater: the scarlet letter repurposed for her reproductive rights awareness group, "A is For."

Winstead grew up in southwest Minneapolis, just 10 blocks away from where she's sitting now eating a bacon avocado omelet. Occasionally, her home state crops up in her jokes, such as when she cracked, "I don't understand why we don't treat Michele Bachmann with the same diligence as other nut allergies."

It's this voice, and her sharp eye for hypocrisy, that has been Winstead's signature since 1996, when she took the helm of the original Daily Show as co-creator and head writer. It stayed with her when she founded the Air America Radio network with Al Franken, and most recently, it is in the pages of her memoir, Lizz Free or Die, which came out in paperback May 7.

Winstead's first headshot after she moved to New York City, in 1990

Winstead's first headshot after she moved to New York City, in 1990

Don't miss our behind the scenes photos of Lizz Winstead...

It has propelled her through countless standup cracks and 30 years in comedy, a milestone that she's coming home to celebrate this Saturday night at the Woman's Club of Minneapolis. Joined by collaborators and siblings, Winstead will host a conversation about her career, her life, and her book.

"I want to talk about the fact that I did weirdly pursue this path that wasn't trying to be anything other than fulfilling to me," Winstead says. "The stories I wanted to tell were the instances and moments and situations where I was treading shit and just kept breathing."

SITTING AT SUNDAY mass next to her devoutly Catholic mother, a 12-year-old Lizz Winstead finally realized what she wanted to do with her life: be an altar boy.

It seemed like a good gig. She could make tips at funerals and weddings, and impress the congregation. So she set up a meeting with her priest.

In Father Hansen's office, Winstead told him about how she practiced playing priest, giving her best altar boy pitch. Hansen responded, Winstead remembers, by turning white and saying that only boys could hold the position.

Confused, Winstead ran through her qualifications: She could hold a big cup, she could fold napkins, she could ring a bell on cue. So why not?

In Winstead's memory, her priest replied, "Well, because it's called altar boy, not altar girl," and advised her to write the bishop if she wanted to press her case.

She did, and never got a reply. What she did receive was a revelation that would later become the backbone of her brand of comedy: Just because someone is in a position of authority doesn't mean that what he says is logical.

Winstead grew up in Minneapolis the youngest — by six years — of five children, a birth order that put her in a performing role from a young age.

"She made her presence known when she was little," remembers her older sister Mary. "She was sort of the Goldy Gopher of the family, but with good teeth."

By the time Winstead graduated from Southwest High School, her main goal was to go to New York and do ... something. But as she explains in Lizz Free or Die, "'Live somewhere in Manhattan' wasn't a degree offered at the University of Minnesota," so instead she started taking random prerequisite classes. Before long, she was spending most of her time hanging out at First Avenue, the CC Club, and the record store Oar Folkjokeopus.

After seeing George Carlin on The Tonight Show, a friend suggested that Winstead try standup. Curious, she started checking out local comedy shows. Six months later — on December 18, 1983 — she signed up for her first gig: the open mic at Dudley Riggs. By the end of the night, Winstead had found an answer to what she would do when she moved to Manhattan. Not long after, she dropped out of the U of M.

"I think from the very first time Lizz started getting on stage, she had literally found her home," says Maggie Macpherson, Winstead's close friend since the early 1980s. "You put her on stage and she was just more Lizz."

For the next five years, Winstead worked the local comedy scene. Before long, she started performing regularly at the Comedy Gallery, which was run by the reigning king of Minneapolis comedy, Scott Hansen.

A vintage polaroid shows Winstead contorting when confronted with Cheney's conservative politics

A vintage polaroid shows Winstead contorting when confronted with Cheney's conservative politics

"Most of the other places were all boys' clubs," Hansen remembers. But he was impressed by Winstead's work ethic, and by the fact that "you could take her act and it would be funny if done by a man or a woman."

"We have comedians come on stage and try to make a statement instead of telling a joke," Hansen says. "And Lizz understood right away that it had to be a joke, and it had to be funny."

Don't miss our behind the scenes photos of Lizz Winstead...

Before long, Winstead started a comedy night with her friends at the 7th St. Entry. She hung out with Roseanne Barr and Tom Arnold — who once borrowed her Ford Escort to get something to eat and didn't return for two days. She slowly learned to work a room.

Winstead's early material wasn't yet political, but it was nonetheless edgy — the kind of stuff not exactly in line with her parents' more conservative values. Macpherson remembers one joke about Winstead telling her mom that her birth control was a shower cap for the cat. But that didn't deter the Winsteads from supporting her.

"They just loved the fact that I'd be on stage, and they'd come to the shows and people would laugh," Lizz says. "Even when they disagreed, they were happy that I didn't have to borrow money from them, I think."

LIZZ WINSTEAD FOUND her comedic voice because of Minnesota Nice.

Winstead played Kathie Lee to Brian Unger's Regis on their satirical morning talk show, <i>O2Be</i>

Winstead played Kathie Lee to Brian Unger's Regis on their satirical morning talk show, O2Be

It was January 1991, and she was in a New York City movie theater on a bad blind date with a guy who kept nodding off next to her. As he fell in and out of sleep, he spilled the popcorn and smeared butter on his jacket.

The butter stain turned on Winstead's native guilt mechanism, so instead of ending the night, she offered to buy him a drink. He agreed, and took her to his regular sports bar in the East Village.

The bar's TV wasn't tuned to a game, though. CNN was on, broadcasting the first night of the first Gulf War: Operation Desert Storm.

"This new war felt different," Winstead writes in Lizz Free or Die. "It felt like a trailer for a movie about war."

Winstead felt sick. But her date — and the rest of the bar — was mesmerized.

"I realized that they weren't reporting the war, they were selling it," Winstead writes. "It was as if at this one moment my personal Pandora's box of media skepticism was opened."

By 1993, this skepticism had matured into a point of view. That year, Winstead flew back to Minneapolis to test her first one-woman show in front of the hometown crowd. For one month, black and gold posters with her face on them adorned the outside of the Campus Theatre.

The poster image for Winstead's first one-woman show, which her sister remembers as "a big turning point for her"

The poster image for Winstead's first one-woman show, which her sister remembers as "a big turning point for her"

Five nights a week, Winstead put on her pajamas, walked onstage, and before a crowd of 300, sat down in a replica of her favorite writing chair, grabbed a remote, and turned on the TV. Over the next hour, the audience watched the war on TV as Winstead provided running commentary.

"It was a big turning point for her," remembers Winstead's sister, Mary. "It was obvious that she had developed this consciousness that she was immersed in that was really starting to inform her comedy. Part of what she was trying to show was: Are we being entertained by this war or are we getting information about this war to help us be informed?"

Winstead's friend Macpherson recalls thatLizz's impulse to dig for a hidden truth had long been part of her personality. Now that spark had found endless fuel in the 24-hour news cycle.

"She was struck early on by how inane it was that we were believing things that were being spoken on the daily news when what was really happening was something different," says Macpherson. "I think, to her, that was not only a really rich source of comedic material, but something that needed to be commented on."

The show was a hit, so Winstead took it to Boston, where it sold out for six straight weeks. After working in comedy for about a decade, Winstead was starting to pick up steam.

By 1995, she got a job in TV, as a guest segment producer on The Jon Stewart Show. Six months later, the network pulled the plug. But the show's bosses moved to Comedy Central, where Winstead decided to pitch them a show.

They didn't bite. Instead, they offered Winstead another idea: a flagship daily show that poked fun at the news. As Winstead remembers, it was as though they had told her, "Don't do the show you just pitched; do your dream show."

"We were not just going to make fun of the news and the talking heads that were everywhere," Winstead writes in Lizz Free or Die. "We were going to make fun of them by becoming them. We would operate as a news organization while acting like a comedy show. It simply had never been done before."

WINSTEAD HIT THE GROUND running. She hired six writers, along with a gang of field producers and correspondents. For the anchor, Winstead wanted Jon Stewart, but he had signed another deal. Instead, the show hired another Minnesotan, Craig Kilborn. The team began the work of putting together The Daily Show.

"Lizz set a tone in that office where it felt like her living room," remembers Brian Unger, one of the show's first correspondents and Winstead's boyfriend at the time. "A bunch of funny, smart people sitting around on couches, smoking, drinking, and doing other substances, where it was so free to come up with whatever joke you wanted. And read that in front of the staff, and we would all judge it by how hard we laughed, and that's what got on the show."

Don't miss our behind the scenes photos of Lizz Winstead...

One of the show's earliest recurring segments was Winstead's brainchild, and put her parents on the air. Jeopardy! was on at 7 p.m. in New York City, but 3 p.m. back in Minnesota. So Winstead had her mother start calling in to leave the final question and answer on The Daily Show answering machine. The messages typically included a lot more. In her book, here's how Winstead describes the average dispatch from Mom:

"'Hi, dear. Today your dad was gone during the show, because I needed a new plunger. I did not understand the Jeopardy! Final today, but maybe you will. Alexander Soldier-nitson, and do not ask me how to spell it, wrote this fiction account of the non-Soviet labor and concentration camping systems. The answer is Goulash Archipelago. I guess it's a book; it sounds exhausting. No one will know this one. Let us hear from you now. Okay, bye!'"

Winstead's mom, with her Minnesotan charm, became an accidental star.

"We'd all look forward to the phone calls from them," says Unger. "Lizz's parents represented the Midwestern sensibility, and the difficulty with which they were trying to decipher this whole new media landscape. And they were naturally funny."

As things came together, Winstead experienced the growing pains of running her first show. She had to learn to pick her battles with the network, to trust her ideas, and to manage a riotous, ego-driven staff of comedy writers.

After two years in the head writer seat, Winstead had gotten the hang of the job. But in late 1997, the show's then-host, Kilborn, made a crude sexual joke about Winstead in an Esquire interview. Comedy Central suspended him for a week, and Winstead quit not long after.

"I think everyone was curious to see how Lizz would respond to the Kilborn situation and leaving The Daily Show, how she would handle it in the book," says Unger. "How giving birth to this wonderful child and leaving it was painful."

In Lizz Free or Die, Winstead devotes a detailed chapter to the Daily Show, but doesn't write about her departure. All she includes about her decision to leave is: "I left the Daily Show a few months before Jon Stewart took over, for complicated reasons that are far less important than my wonderful experience of creating it and bringing it to life."

When asked about why she demurred, Winstead doesn't pull any punches.

"I don't want to step on people's toes, but I also wanted to write about my time there. I have this piece of history that only I and a few other people have," Winstead says. "If I was that person who was going to gossip [about quitting], I would have written that book right after I left the Daily Show, when people actually gave a fuck."

Winstead remains frequently associated with The Daily Show, and is often introduced as one of its original creators. She wears the title with pride.

"What I hope is, when people do introduce me as that, it's because my body of work since then has an obvious tonal familiarity with that," she says. "I feel happy that I could lay the foundation for Jon [Stewart] to come in. That's the sign of a good thing, like when you redo a house and you go, 'God, the bones of this house are so fucking strong.'"

IN HER 52 YEARS, Lizz Winstead has missed the Minnesota State Fair only three times. This past summer, she was walking through the fairgrounds with friends on a Saturday afternoon when she spotted Michele Bachmann doing a meet-and-greet at a radio station's gazebo.

Winstead had been skewering Bachmann for years — since at least 2008 — but had never met her in the flesh.

"Those eyes of hers are real," Winstead says. "I was surprised that nobody in her wheelhouse was like, 'Get away from that person, she makes a living making fun of you.'"

Shocked, Winstead did the only thing she could think of: take a picture with Bachmann.

The move was lifted from her brother's playbook. Gene Winstead is the mayor of Bloomington, and even though it's a nonpartisan post, Gene identifies as a moderate Republican.

Gene views his work as less politics, more community service, but during planning for the 2008 Republican National Convention in St. Paul, he took a leadership role.

"The mayors of Minneapolis and St. Paul, obviously Democrats," he says. "I was the closest thing we had to a Republican."

At event-related dinners, Gene would snap pictures of himself with party bigwigs like Karl Rove and, yes, Bachmann, "Just to get Lizz's blood pressure up," he says. "I'd send it to Lizz, and she'd text me right back like, 'Oh, have you taken a shower?'"

That kind of quip has, in recent years, become Winstead's bread and butter. Since 2005, her work has increasingly focused on roasts as well as biting standup and political commentary — frequently providing all three during guest appearances on MSNBC and other networks.

"What she does now is political spin on a big league basis," says Gene.

After leaving the Daily Show, Winstead moved to L.A. and created a show for the Oxygen network called O2Be. Though critically acclaimed, Winstead's harder-edged brand of comedy was a tough sell in the post-9/11 media landscape, and the show was cancelled after its first season.

She tried her hand producing a reality dating show for MTV, but after realizing that it was a personal hell, Winstead left for an exciting new project: co-founding a national progressive radio network with Al Franken. In seven months, she put together Air America Radio, including her own show with Public Enemy's Chuck D and the then-unknown Rachel Maddow, whom Winstead had plucked from a small local radio show in Massachusetts. For two years, the three bantered "to the left of the dial."

By 2005, Winstead's show was losing steam. She returned to working for herself and put together projects including "Shoot the Messenger," a live show she performed with a comedy troupe on Monday nights.

Then, in 2010, Winstead's mother got sick. At the same time, the national political scene was taking a sharp right turn, smack into her sweet spot.

This time though, Tea Party politics did more than just make Winstead angry. They made her want to tell her own story. By the end of 2010, she returned to Minnesota to be with her family and to craft the "messays" that would become Lizz Free or Die.

SIX MONTHS INTO her Minneapolis writing retreat, Winstead needed to get back to New York. She had a truckload of stuff and two dogs with her, and planned to drive back east over the course of a day or two. But one morning, her friend Maggie Macpherson, whom she was staying with, came downstairs.

It was mid-2011, right around the time when "all hell was breaking loose with women's reproductive rights," Macpherson remembers. "Lizz was sitting on the couch, and she's going, 'I've got the greatest idea.'"

Winstead had decided to host fundraisers for Planned Parenthood all along the drive from Minneapolis to New York.

"Lizz was always trying to shine a spotlight on stuff she thought was incredibly wrong, and find the funny in it," says Macpherson. The right-wing attacks on women's health care were a perfect foil.

On her way back to New York City, Winstead stopped in six cities over ten days for a Planned Parenthood standup tour. As she read early chapters of Lizz Free — including one, "All Knocked Up," about her experience with abortion in high school — she was amazed by the response. She had found her next project.

Since then, Winstead has created about 30 fundraisers for Planned Parenthood, along with a handful for other women's health care organizations. All told, they have raised over $2 million. They've also provided the inspiration for a documentary Winstead is putting together about the state of women's health care around the country, which will be her focus for 2013 and 2014. She plans to start filming this summer.

"I'm the person who can drive around and talk to people, and through storytelling and outrage I can make one piece of art that can go in movie theaters and show people what's happening," Winstead says. "I feel like what Michael Moore has done for guns and labor, I kind of want to do for reproductive rights." In some ways, she continues, this situation is exactly what her radar for absurdity has been tuned for.

Unger agrees. "What she's doing now, as a feminist, as a comedian, and as an advocate, is a perfect blend of what her talents are," he says. As Winstead prepares to celebrate 30 years of comedic truth-telling, he continues, "We're just beginning to see where her talents go."

Don't miss our behind the scenes photos of Lizz Winstead...

Lizz Free or Die: The Book, The Career, The Life
with Brian Unger, Frank Conniff, and Winsteads
Saturday, May 11. VIP Reception 6:30 p.m., Doors at 7, show at 7:30.
$30 regular, $60 VIP at Etix
The Woman's Club of Minneapolis
410 Oak Grove Street, Minneapolis