A year ago, Lizz Winstead probably didn’t expect to be performing on a makeshift stage to fewer than two dozen people in kayaks on a lake in the woods of Minnesota, but then little about 2020 was foreseeable. The Daily Show cocreator and former head writer has been doing political comedy for decades, from one-woman shows about the Persian Gulf War of 1991 and 9/11 to a collection of essays that discuss her politicization to a stand-up tour benefiting Planned Parenthood and NARAL. In the midst of last year’s protests against racism and police brutality, Winstead filmed two stand-up shows—one in late September and another in November, after the election. They form the basis of her new special, Corona Borealis. In it, Winstead talks about the pandemic, racism, and the various ineptitudes of the Trump administration and also features a conversation with Minneapolis city councilwoman and poet Andrea Jenkins, who made history in 2017 as the first Black, openly trans woman to be elected to office in the United States.

—Rima Parikh

RP:: How did you negotiate being a white person talking about racism without overstepping?

LW: You hear white liberals say, “Oh, those Karens,” as though they’re not responsible for Karens. I really wanted to put out that they are a product of us not calling out the people in our lives who are doing that.

RP:: What went into the choice to include a conversation with Jenkins about defunding the police?

LW: The way to talk about George Floyd was, for me, to have Andrea Jenkins drive a conversation where I didn’t say much. I wanted to showcase Andrea in that piece to make sure the correct voices are being heard.

RP:: You had a lot of older white people in the crowd at the first show who might have been a little more resistant to the idea of defunding the police. Were you thinking about how to reach them?

LW: I think that when people hear that phrase, bristles go up. I feel it’s just like saying the word “abortion.” People are like, “Don’t say the word ‘abortion.’ ” And it’s like, I’m not going to not say words. If we allow the fear of words to stop us and we dance around them, then we end up never talking about the actual thing we need to be talking about.

RP:: How do you think political comedy will change in the Biden-Harris era?

LW: Back in the day, every late-night show was like, “We don’t want to do a lot of political jokes.” And then every late-night show jumped on Trump because it was buffoonery. So what I’m curious about is: Are they going to go back to, “Oh, now that it’s Biden, we’re not going to talk about politics anymore”? Or are they going to be brave enough to say, “The best time to talk about politics is when you have somebody who has purported to be someone who will listen to different points of view and listen to change”?

RP:: How have your politics and comedy changed over time?

LW: I don’t shy away from how I’ve evolved, because the power structure of our politics hasn’t. There’s still money in politics—people who come into our political system from a system that is run by money. Trump made it harder to be a political comedian, because basically you’re talking about somebody like, “What is wrong with this person?” It’s like analyzing a sociopath versus doing political comedy. That’s what political comedy was for the last four years: the anatomy of a sociopath. That’s not political comedy. I’d like to get back to the matter of holding people accountable through humor.

RP:: What surprised you about filming this special?

LW: When you film a special in the woods, your natural sound is crickets. So every time I was standing onstage in a normal pause, there would be crickets cricketing, so it sounded like I was bombing constantly. Some of that had to be edited so there weren’t so many crickets constantly cricketing. I think the fact that people were so desperate to want to come and hear anything about the year [surprised me]. People were in such an overwhelmed, emotional state and were still game. I do often think, if you can still laugh, you haven’t lost your capacity for hope.