By Jesse Marx
By Chris Parker
By Jake Rossen
By Jesse Marx
By Michelle LeBow
By Alleen Brown
By Maggie LaMaack
By CP Staff
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!'"
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
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.