Comedian Lizz Winstead celebrated 40 years in the business this month, four decades after taking a dare to perform at an open mic. She’s celebrating with her annual year-in-review at the Parkway this week, titled “2023 and Me: Breaking Down The Year in DNA-holes,” with special guests, finger-style guitarists Sam Breckenridge and Ben Abrahamson.
Winstead says her journey began four decades ago. A class cynic (as opposed to a class clown), she was a punk-rock kid at the time. “I was going to see bands every night, and I was kind of just fucking around with my friends and being funny,” she tells me.
Winstead thought she might become a history teacher, and did some theater. Mostly, she was interested in railing against the Catholic Church and being a feminist.
Winstead acted on a dare by her roommate to perform five minutes at Dudley Riggs’ Experimental Theatre Company (ETC) Stage. At the time, Dudley Riggs had two venues — one was the improv theater Brave New Workshop and other was the ETC venue, where stand-up comics and other miscellaneous acts would perform.
She doesn’t recall now what notes she scribbled down before her first five-minute set, except that birth control was part of her act (no surprise, as reproductive justice has been a major theme of Winstead’s advocacy her whole life).
Winstead remembers about 300 people in the room, though she couldn’t see anyone past the first row and a half. “I remember getting a laugh and feeling like, this is really fun,” she recalls. “I’m the youngest of five kids, and it was really great to be on stage and speak for five minutes without somebody interrupting me.”
Her first set went well, Winstead went back the next week, and bombed. Her third time, she did somewhere in between. She kept doing it.
The 1980s, Winstead tells me, was a kind of golden age for stand-up comedy in Minneapolis, with six full-time clubs operating for a number of years. This was after Louis Anderson had moved to Los Angeles, and Joel Hodgson from Mystery Science 3000 was headlining. Besides Dudley Riggs’ ETC, there was Scott Hansen’s Comedy Gallery in downtown Minneapolis, where St. Thomas University is now. “That was arguably the greatest comedy room I’ve ever played, even now,” Winstead says.
There were other clubs like the Rib Tickler, where Acme is now, and places like Market Barbecue, and a number of other clubs in St. Paul and Minneapolis. For a time, Winstead ran a room with Tom Arnold at the Seventh Street Entry, and would do one-nighters in places like St. Cloud, Fargo, Alexandria and Grand Forks.
Winstead attributes Minnesota’s embrace of comedy to its strong storytelling tradition, over campfires and through the winter. “I think that breeds people who are willing to go on a journey with you,” she says. “And it breeds people who are really good storytellers. She notes that time period produced a vibrant music scene as well as journalists like David Carr and Michele Norris. “The Scandinavian politics that have landed here really also helped people cheer for you,” she says.
By the time Winstead left Minneapolis in 1987, she had people who knew her act and could help her get her feet wet elsewhere — first to San Francisco, then to L.A. and later New York in 2003.
Winstead got her first big break at a tiny club in San Francisco called the Holy City Zoo, which sat about 60 people. She had just performed at some place in the middle of California, which had not gone great, and called Holy City Zoo to do a set to get that bad show out of her system.
“So I go up, and I just started talking about this horrible show and the people that were there, and this guy in the audience was laughing a little bit too hard, and a little bit too loud, in this really obnoxious way,” Winstead says. It turns out it was Robin Williams, and he thought Winstead was hilarious. He introduced her to his manager, and soon she was on an HBO special called “Women of the Night,” hosted by Andrea Martin from SCTV.
Throughout her career, Winstead has been on the front end of new trends. She co-created both “The Daily Show” (quitting after a sexist comment made by the first host, Craig Kilborn) and also Air America, where she was a co-host with Rachel Maddow and Chuck D. She’s also published a book, “Lizz Free or Die,” founded a nonprofit called The Lady Parts Justice League (now Abortion Access Front), and currently co-hosts a podcast called “Feminist Buzzkills Live!” with Moji Alawode-El.
Looking back on her career, Winstead says she feels pride for being part of “The Daily Show” and “Air America,” but feels the most pride for speaking up when the opportunity arose.
“I’m happy that I pushed back when I could have just sucked it up and probably had an easier road,” she says. “But at the end of the day, I feel really good about the results of me pushing back, because I see the products. A, they sustain, and b, I can sleep at night.”
See Winstead’s takedown of 2023 at the Parkway Theater on Saturday, Dec. 30, at 7:30 p.m. ($50-75). More information here.
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