“Vote for Lizz Winstead! Oh wait...But, fuck—I would if she ran for something.”—Sarah Silverman
“Lizz Winstead is a warrior.”—Sandra Bernhard
“Do you really need to be so fucking smart? It’s irritating.”—Lewis Black.
Seventeen years after giving birth to The Daily Show, one of the most influential commentaries on the zeitgeist, Lizz Winstead should be a household name, like Tina Fey or Amy Poehler. Or Jon Stewart. Yet outside the comedy world, she’s unknown. She tried to recreate the magic with projects like Oxygen’s 02Be or the off-Broadway play Shoot the Messenger, both short-lived morning and daytime talk show satires. But apparently The Daily Show can’t be duplicated. Not even by the woman who created it.
But Winstead’s not bitter. She’s been away from the fake news grind for so long that she can sit back and brag about what her baby’s become with Jon Stewart at the helm. “What I’m happy about is the foundation was laid that somebody could come in and do that,” she tells me. “I feel really good about that. I feel really good about my instincts.”
“The drive for me to do comedy was to be able to say something uninterrupted,” she goes on. “I didn’t want to be on TV, I didn’t want to be in movies, I didn’t even want to be on The Tonight Show. I just wanted to get on stage and call bullshit.” Maybe that’s just something she says now that she hasn’t had a tremendous amount of traditional success. Or maybe it’s something that’s always been true. It doesn’t really matter. Winstead practically invented the way we call bullshit now. And three decades after she first stepped on stage at a Minneapolis comedy club, she’s still doing it.
For the past two years, Winstead has used her politically conscious brand of comedy and her cache of celebrity friends to raise money for reproductive rights groups like Planned Parenthood and the National Abortion Rights Action League. (It’s a cause particularly near to her heart as she had an abortion at 17 after getting pregnant the first time she had sex.) Her latest creation is LadyPartsJustice.com, a site that uses funny videos and funny writing to draw attention to anti-abortion laws and the politicians that sponsor them. Kind of like The Onion, but with real news.
“My approach to talking about politics has always been to treat it like you’re gossiping about people from high school,” she says. “Hopefully we can make local douchebags famous and get people registered to vote in their states.”
Her first Lady Parts Justice event, the “Clear Eyes, Full Hearts, Can Choose” telethon for Texas abortion funds that have been stifled by new government restrictions, was cobbled together in eleven days to accommodate co-host Sarah Silverman’s schedule. On a Monday night in November, one giant stuffed vulva and a coterie of actors, musicians, writers, and comedians gathered in a New York City basement to make some jokes and fundraise. There was only one problem: you need Internet to live-stream an event.
“We ran upstairs and knocked on the neighbor’s door and said, ‘Are you pro-choice? Can we use your Internet?” Winstead says. “So we ran a wire from the basement we were in up through the building into this woman’s apartment and her crazy landlord almost cut it because she didn’t know what was going on.”
The show did well. Really well. “You wake up and there’s no money and you go to bed and there’s $54,000 from a thing that was slapped together in a basement,” she says. “It felt really great.”
Winstead whirls into the cozy Brooklyn coffee shop down the street from her apartment and hugs me. I’ve been waiting for an hour. Her Google calendar (she “lives and dies by it”) didn’t save our meeting. She apologizes profusely, curls up across from me, and begins to, as she calls it, gab. The 52-year-old isn’t conventionally pretty, yet she’s disarmingly attractive. Makeup-free in a green knit turtleneck, she exudes the warmth of the Midwestern mother of a friend whose house you’d rather spend more time at than your own. She’s as inviting as she is candid and self-deprecating, answering questions like, “Did you imagine how influential The Daily Show would be?” with “Of course I did, because I’m brilliant. Can you imagine if I said that?!”
The youngest of five children raised by “crazy, crazy, crazy conservative” parents, Winstead had to be loud to be heard. “Mom had a great sense of humor and dad had a great memory, he was the storyteller,” says Winstead’s older brother Gene, who is the mayor of Bloomington, Minnesota, home of the Mall of America. “The whole family would pipe up all the time, so she being the runt would have to pipe up that much louder. Everybody talks, nobody listens.”
“My dad always said, ‘I raised you to have an opinion, I just forgot to tell you it was supposed to be mine,’” Winstead says, turning up her usually subtle Minnesotan accent . “I was never told, ‘You should be doing something else, you should be trying to get a job where you could have some stability.’ It was always just, ‘You’re great!’ or, ‘Have you ever thought about calling The Johnny Carson Show and just asking to be on?’”
Ex-Daily Show correspondent Brian Unger—also an ex-boyfriend who met Winstead at a Halloween party in the ‘90s while they were both on the “youthful indiscretion” of ecstasy—admires Winstead’s ability to turn any workplace, even the writers’ room at The Daily Show, into “a comfortable Minnesota throwback living room.”
It’s actually Winstead’s own comfortable throwback living room where Sarah Silverman is seen lounging in one of the most notoriously depraved scenes of the 2005 comedy documentary The Aristocrats. Silverman first met Winstead in New York in the ‘90s and the two reunited in 2001 at a party in L.A. “She was in a hammock and embraced me so warmly,” Silverman tells me. “I fell in love with her that day and she’s been one of the greatest friends of my life ever since.” (Silverman once sublet Winstead’s apartment and broke “beautiful” wooden chair. “She said, ‘Oh Marge—she calls everyone Marge—that’s just stuff. I don’t care about stuff.”)
“Lizz likes to relax,” says Gene. Once when he and his wife were on vacation he entrusted his teenage sister to watch his daughters. “She was a disaster, a terrible babysitter,” he says, laughing. “We found out when we got back that all she did was stay in our bedroom and watch MTV the whole time.”
This is the kind of story Winstead might use to justify her long-held conviction that, other than her two dogs—Buddy, a Corgie-Spaniel mix, and Edie, a collie-shepherd blend named after Edie Beale from Grey Gardens—she wasn’t meant to be a mother. It’s a certainty that’s been tested over the years, by her own mother who devoted her life to her children, by boyfriends determined to change her mind, and by a society still uncomfortable with the concept of a woman who doesn’t want to have kids. Now that she’s 52 and kids aren’t exactly an option, she has no regrets.
“I couldn’t do this shit if I was going to devote myself to kids and a family,” she says as a baby, as if on cue, cries next to us in the coffee shop. “Without sounding pretentious, this is my calling, and part of a calling is having an unending energy and drive for the thing you believe in, right? That’s what parenting is, an unending drive to be a parent. For me, it’s this other thing.”
“I realized I’d started replacing ‘I feel’ with ‘I think’ in my jokes,” Winstead says, reflecting on her early days in standup, which started 30 years ago this month. “And when I started saying ‘I think’ the audience was shutting down. Just the subliminal nature of being on stage and making a declarative statement rather than a passive one. When I noticed that I thought, ‘Well, if I’m going to say I think, I might as well say I think things that are controversial or interesting or thought-provoking.”
The birth of The Daily Show is chronicled in Winstead’s 2012 book of essays, Lizz Free or Die. While on an epically bad date with a man draped in Yankees memorabilia (the kind of guy who “probably wouldn’t go down on you”) she saw a TV news special about the first Gulf War. She hated the videogame-like coverage and was later disgusted by the tabloid reporting on stories like Rodney King, the Menendez brothers, O.J. Simpson, and baby-shaking nannies. All this was fodder for her one-woman act.
Meanwhile, in 1995 Winstead moved into the same apartment building and befriended Madeleine Smithberg, then the producer of The Jon Stewart Show on MTV. Smithberg hooked Winstead up with a job on the show. When it was cancelled months later, the executives, now running Comedy Central, approached the two about making their own show.
“I was like, ‘Oh my fucking god, are you kidding me?’” says Winstead. She was 34. This was her dream job.
Winstead insisted that the show would be a newscast written by comedians. In its first few years, when Craig Kilborn was the host, the show was more like The Colbert Report than The Daily Show with Jon Stewart in that no one ever broke character. Winstead admits she was a tough boss, maybe too tough, inexperienced in delegating and fiercely protective of her vision.
“That show, when Lizz was the head writer, to me was the smartest show on TV,” says former producer Hank Gallo. (She credits him with giving her first big break with a positive review of her act in the New York Daily News; she was the first and only comic to send him a thank-you note.) “There weren’t any other comedy shows or late night shows with Pol Pot jokes. Our first year on the air there was a lot of news about Pol Pot and all of a sudden we had Pol Pot jokes and it was terrific.”
Still, Winstead and the show’s other pioneers cringe at the frequently spouted statistics that most young people get their news from The Daily Show. “Snark and attitude don’t make up for reporting,” says Unger. “Trying to be funny isn’t a substitute for good journalism.”
Winstead’s departure from The Daily Show, just two years after launch, is less well-documented. She quit in 1998 shortly after Kilborn told Esquire magazine, “To be honest, Lizz does find me very attractive. If I wanted her to blow me, she would.” (She’s never confirmed that this was the reason she left.)
Comedian Lewis Black says Winstead’s exit was “one of the sad days of my life.” “She doesn’t have the patience for an idiot, that’s why I like her,” says Black, who still appears on The Daily Show. “She was gone and he was still there and it was her show and I thought that was fucking appalling.”
Why isn’t there a feminist version of the gay pride parade? That’s what Winstead wants. She calls it the “V to Shining V.”
“I’m always so surprised that women have not taken a page from gay pride and said, ‘Why don’t we just do a super fun music-bands-comedy-parade-party celebrating us?” she says. “You tie that celebration in with what’s going on, a call to action kind of thing, and that way you have something in place so that every year nobody has to worry about how we’re going to get out the vote for midterms.”
Right now, she’s busy preparing for her annual year-end show in Minnesota, pitching a sitcom about her family to networks, and, most importantly, getting LadyPartsJustice.com off the ground. The Clear Eyes, Full Hearts, Can Choose telethon was just the beginning. Once the website, which currently looks like a 404 page playing a video on loop, is running in full force, Winstead wants to launch “a 50-state douchebag strategy.” That is, getting celebrities to host events in their hometowns that offer voter registration and information on bad local politicians. “It doesn’t have to be big, it just has to be in the state capitol in the backyard of the people who are making these crappy decisions,” she says. “If you have groups of people going to the Capitol, with local news covering it, they can’t deny the numbers. They can’t hide under a rock.”
Longtime friend and fellow comedian Sandra Bernhard considers Winstead a modern-day Gloria Steinem. “Lizz is just on her path, she’s dedicated her life to the cause of women’s rights,” Bernhard says. “You have to have the inner strength to commit to it. She’s constantly being attacked by the right and the crazies but she seems to be impenetrable.”
Winstead does have haters. She is, of course, an abortion rights advocate in a nation where only nine states have not passed abortion-restricting laws. Blog posts on conservative sites like Red State and NewsBusters deride her as “an insensitive jack hole” and condemn her for making jokes about pro-lifers. But she’s not afraid of her ideological opponents. It’s those who hate her without being able to articulate why who really get to her.
“People say, ‘you’re ugly, I would never fuck you.’ Or, I love when people say, ‘you’re old.’ It’s like, you know, there’s this thing that happens every year, I get older, and apparently that’s a character flaw,” she says. “But I do get mad when there is so much sexism. I’ve had to scream at people on the left for calling names at Michelle Malkin or Ann Coulter or Sarah Palin. I don’t accept that. There’s enough ideas that come out of their mouths and brains that you can tear them down about, but when you start calling them names that doesn’t tell me anything. It’s just lazy.”
These days, Winstead’s is probably just as well known for her contribution to The Daily Show as for her contribution to Twitter (she has 85,000 followers). Twitter isn’t just a way to spread her political message, it’s how she tests material. She’ll often post a story she’s read along with a joke—the ones that get a positive response go in her file. Like in a comedy club, sometimes her tweets kills and other times—like when, she made fun of believers in divine retribution with a joke about the Moore, Oklahoma, tornado—it backfires.
“Everybody is in my weird comedy experiment,” she says. “Some people like it and some people are like, enough.”