Lizz Winstead is one of the top political satirists working today. As co-creator and head writer of Comedy Central’s The Daily Show, Winstead changed the way people get their news. In 2004, Winstead also co-founded Air America Radio, while also co-hosting “Unfiltered” every morning with the Rachel Maddow and Hip Hop legend, Chuck D.  Her book of essays, Lizz Free or Die, was published by Riverhead Books in 2012.

Originally from Minneapolis and now a resident of Brooklyn, N.Y., Winstead continues to make numerous television appearances, including Comedy Central Presents, HBO, and CNN, as well as her regular commentary on MSNBC.

Back in the Twin Cities — Winstead notes that she does live in Minneapolis about half the year now — for her annual year-in-review show at the Parkway Theater in Minneapolis, Lizz Winstead visited The Current to talk to Jill Riley about how the year-end show comes together … while making a few wry observances along the way. Listen to the conversation using the audio player above, and read a transcript below.

Interview Transcript

Jill Riley: I'm Jill Riley, you are listening to The Current's Morning Show, and today is Thursday, December 28. Looking forward to the weekend; about an hour ago, I did the rundown of the Weekend Gig List, and it's not just New Year's Eve — I mean, there are plenty of shows happening all weekend long. So a lot of options for you if you want to head out and celebrate or just bid farewell to the year 2023. Plenty of options out there. And we've kind of made it this annual tradition here on The Current to welcome back a special guest each year, because she has made it a tradition to visit the old hometown and say farewell in a very funny way to the year, and that would be comedian Lizz Winstead, who is with me this morning. Hi, Lizz. How are you?

Lizz Winstead: Hi, Jill. I want to say that my tradition kind of expanded in the sense that I actually this year also bought a house here. So I'm living here part time.

Jill Riley: OK! Congratulations!

Lizz Winstead: Yeah. So I am a Brooklynite and I'm a Minneapolitan.

Jill Riley: And you just couldn't stay away.

Lizz Winstead: You know, we can't. We come back. You know, I'm not from Akron. I'm from Minneapolis. So I feel like I should be spending more time here. Oh, it's not a bad place to be. No, it's awesome.

Jill Riley: Yeah. I thought about leaving many years ago, and I thought that radio would take me far to a land and maybe an exotic place like New Mexico on an AM station where... Because that's how I was told this whole thing worked.

Lizz Winstead: Radio Kirk.

Jill Riley: Exactly, I'm telling you, I'm so happy that I've been able to stay in my home state because I think I'd have a hard time jumping somewhere else.

Lizz Winstead: It's good here. You know? It's good here. When you're complaining, it's good here.

Jill Riley: Yeah. Well, you betcha. "2023andMe: Breaking Down The Year in DNA-holes." That's the show coming up this weekend.

Lizz Winstead: Hey! You said it without getting beeped.

Jill Riley: Yeah, that's right.

Lizz Winstead: Good job.

Jill Riley: Well, you know, the holes in the DNA. 

Lizz Winstead: Yeah, DNA, there's holes in DNA, for sure.

Jill Riley: All right, your two shows coming up this weekend at the Parkway Theater. And Lizz, for anyone who's not familiar with what you do with the show, can you just kind of give us the overall idea of what you do with these shows each year?

Lizz Winstead: So, it's a whole multimedia show where I have sound clips, and I have graphics, and I run through the year — the good, the bad, and mostly the bad. So I try to do it, since we all are exposed to so much information, I try to find like, I dig into the vault of like obscure clips from the people that we rage against. So it's like, "Oh, I bet you missed this one." And people are like, "That did not happen." And it's like, no one believes me, so I have to now just come with proof.

Jill Riley: You could do anything, and I'd believe it because I'm like, "Oh no, that seems like a thing that could have happened." Yeah. 

Lizz Winstead: So I just bring receipts. And then, you know, I just lay it out, whether it's pop culture, whether it's politics, whether it's, I mean, this year has been just a lot. There's a lot, you know, we have an ex president who has several, I don't know if you've heard about, indictments. You know, reproductive rights is on the chopping block. It's been the year of Taylor Swift and of Ozempic and have the weird Chinese balloon...

Jill Riley: Oh my gosh, I forgot about that!

Lizz Winstead: And somebody saw aliens among us. This is the whole thing. I was looking at my list, and it's like, you run down your things, and you're like, "These are all the big stories." And then I was like, "Wait, the Queen died! The Queen died, I gotta put that in."

Jill Riley: That was this year!

Lizz Winstead: That was this year, and you're like, "Oh my god, that was this year!" Right? You just cannot believe all the stuff that was this year. So trying to wedge the whole year in is hard enough. And then I am sprinkling it with anecdotes from sort of touchstone moments of me doing this for 40 years, because I have no skills, so I had to stick with it. And you know, from my beginnings here to Air America Radio with Rachel Maddow and Chuck D, to the Daily Show, to then sort of merging my comedy and activism together and doing this work trying to save reproductive rights for all of us. So it's a long, storied career full of stories I've never told on stage before and I thought I'd weave that in as well.

Jill Riley: I'm here with Lizz Winstead here on The Current's Morning Show. All right, you mentioned 40 years in comedy. And so my understanding is that this all started at an open-mic night, and that's where my understanding ends.

Lizz Winstead: Yeah.

Jill Riley: Can you bring us back to December of 1983?

Lizz Winstead: Indeed. Well, it's funny because, you know, worlds collide so much in the Twin Cities. I was living with Danny Murphy from Soul Asylum at the time; he was one of my roommates. And I was just such a cynic that my housemates were like, "You should just try standup." And so I showed up at Dudley Riggs on one of those open-call nights for amateurs, and the room was packed, black as pitch, so I couldn't see anything on stage. You know, I think I told some dirty jokes. I think I sort of just bitched my way through with concepts like, "I really believe that male Great Danes should be required to wear underwear in public." I think that was one of my early pieces of hilarity. I think one of my other early jokes was, "My mom showed up at my house unexpected, and I had to tell her my diaphragm was a bathing cap for my cat." Which for those youngsters out there, look up diaphragm, find out what it is, because I don't think people use them anymore.

Jill Riley: Unless you kick it old school.

Lizz Winstead: Unless you kick it old school. And so just you're pure — this is like a classic story — you're pure adrenaline, you do pretty good, and the audience is rooting for you because the emcee is like, "It's her first time!" So then I'm like, "I'm great at this!" like a complete idiot. Second time I go on, totally bomb, because I had all this unearned confidence. So then I'm like, "Well, I gotta try for a third time to see am I good or am I bad at this?" And I was completely middling, so I was like, "That tells me nothing." So I did it a fourth time, and cut to 40 years later, where I'm like, "I'm gonna get on stage and see if I'm good at this one more time!" And here we are.

Jill Riley: Here we are, the year — well, almost done with the year 2023. You know, Lizz, in those early days, were you trying to write jokes all the time? What I love about your humor, or anybody who has like good observational humor, and then that like reaction to what is happening, but also finding that ridiculous side of life. Is that something that you were always kind of a natural at doing?

Lizz Winstead: I think I was a natural at seeing and snarking, right? So I would see something, and I would immediately form an opinion. And of course, knee-jerk opinions, always the best opinions! But I kept doing that. And then I kept a notebook, and if I saw something, I would write it down. And now I have used social media to test balloon before I even go to stage. So I'll have a premise, or something will hit me in the news that I will just post as a tweet — I will deadname Twitter, it's my only time I'll deadname anything or anyone, is Twitter — and then people will react, and they'll react in ways that help me understand what they want to hear about from me, right? So it's like, if 15 people are like, "Why does Jack Smith do this?" I'm like, "Oh, that's something people want me to answer comedically." And then I can write my jokes according to what the people want. So that's kind of cool. And if you look at my favorites on any of these platforms, I look like a giant narcissist, but it's just that I save those as ideas and throw them into documents. But yeah, that has been an incredible writing tool for me, which was unexpected.

Jill Riley: And it's always good to have a good snark support around you. Really, like the people that we choose to, you know, we surround ourselves with people who, when you do observe something, and I kind of think in my brain, "If my best friend was here, what would I say about that?" Because she's such a safe space.  And it's OK to laugh.

Lizz Winstead: Yeah, exactly. And I pretend that the stage is a safe space. But for some weird reason, it kind of is, because, like, I mean, the past decade has been an emotional roller coaster for everybody. We have been through so much. There's been so much change. There's been so much tentativeness, and it's been scary. And so to be able to have a catharsis every year, and to remind people that you can find humor in pain and tragedy and hypocrisy, and when overlords are being terrible. It's nice to gather in a room and just, you know, have feelings about it.  Yeah, it's OK to laugh, especially when you're in pain, it's OK to laugh through it. And people often say to me, you know, "Your act seems to skew liberal. Are you a liberal?"

Jill Riley: Have you met Lizz Winstead before?

Lizz Winstead: And I was like, "Yes," but also, like, I get to be that. I get to have my opinions. It's like, you wouldn't walk into a butcher shop and say, "For 40 years, you've only been selling meat. Why are you selling any fish to the people who like fish?" It's like, "Because I sell meat." So you know, come and purchase what I'm selling, if that's the kind of thing you want, and don't bug me to do something I don't do well.

Jill Riley: Lizz Winstead onstage this weekend at the Parkway Theater for two shows. So that'll be Saturday night and Sunday night for New Year's Eve. It's "2023andMe: Breaking Down The Year in DNA-holes." Lizz, have you ever had a year where you're looking back and you're kind of gathering your material, and you go, "I don't know, this year was pretty good!"

Lizz Winstead: Never. Not one time. In fact, it's been the opposite, where it's been, how am I going to get through this year? I mean, there was one year, the year that Prince died and Bowie died and Trump got elected, and Bill Cosby and #MeToo. I was like, "I have to do a show that tackles sexual assault, the up-ending of our country, my two favorite performers of all time have passed away, and I gotta bring this to the world." But I found a way; I always find a way. And you can always leave things out. You know what? It's my interpretation of the world that happened, and it's not important for me to cram a big story in if it's going to cause pain. It's my job to really just present the world as I know it, because 99% of the time, I'll hit what you want to hear. I kind of equate doing a year in wrap-up like going to see the Stones. It's like, you're not gonna hear every song. But you'll hear a lot of the songs, and you'll have a great time. So if you don't hear your favorite song, know that there's just not time, unless you want to wear your pajamas and come for eight hours, which nobody wants.

Jill Riley: Marathon.

Lizz Winstead: Yeah.

Jill Riley: I'm here with Lizz Winstead on The Current's Morning Show. So Lizz, when we first started talking, you kind of named some of the big events that happened in the year 2023. And then some that I had that reaction of going, "Oh, yeah — oh, that was this year!"

Lizz Winstead: Yeah.

Jill Riley: "What? That was this year." Is there a particular story — and I think I suffer a little bit from like recency effect, where at the end of the year, whatever happens at the end of that year, in particular, it's like, that's the thing that sticks in my mind. Like, I don't know, how many people went home for the holidays or gathered with relatives, and like the state flag came up or, you know, it's like, that's the story that's been sticking in my mind. And only because I just really think that that committee and commission should take a second look at bag, the sketch of bag.

Lizz Winstead: I mean, some of the ones that came in were kind of inexplicable. There was one where there was conjoined loons ascending from the water. And I was like, you know, when I was on Air America Radio, I actually did a story about what creates these things in fish and wildlife, and it's pollution. So if you have two loons that are conjoined...

Jill Riley: Something happened.

Lizz Winstead: It's not a celebration of our waters, per se; it's more like these loons need help.

Jill Riley: Yeah.

Lizz Winstead: There was another — and loons was a huge theme — there was one loon that was wearing like a choker from Claire's and had like a sketchy, kind of like, it looked kind of like it was running a brothel. And if loons was the sort of go, there was not one Mike Lindell; if you're gonna have a loon, I mean Mike Lindell seems to be able to work well. But yeah, some of the [designs], I was just like, the flag really felt to me like it was like, "Are we now called Meh-nesota because it was like, 'OK, that flag's fine.'" I mean, anything to get rid of that old seal, because that was some — no. Just big fat not our values.

Jill Riley: I just, I don't, honestly, when it comes to the Minnesota State Flag, this is a discussion that I've had with some family and friends, it's like, it's not real top of mind for me all the time. So the idea is, "OK, well, it's time to rebrand, it's time to have this new emblem and this new symbol," I kind of went, "Sure, let's do it."

Lizz Winstead: But like, are we gonna do it on Canva? Like, really?

Jill Riley: But what are we doing? I'm very much a process person, too. And it's a good thing I'm not on these committees and commissions, because I think two hours to deadline, I'd be throwing in that, like, "You know, you guys, I really think we should go back to the drawing board." And then everyone would go, "Aaaaaaah..."

Lizz Winstead: When I looked at it, I felt like, OK, it felt like what somebody just bulleted it out what should be in the flag, so like, "OK we need a star, and then we want to represent the blue and the water." And it was like, "OK, here, how about this? Here's a star on blue." OK. You know, that wasn't the design that was just a... and there it is, and there we have it. So yeah, I will be talking about the flag.

Jill Riley: Yeah. Well, how could you not?

Lizz Winstead: How could you not talk about the flag? And "bag" was really good I have to agree.

Jill Riley: The memes that were coming out of it, it's like, again, it's what you do, Lizz: It's finding the humor in the ridiculous.

Lizz Winstead: Yeah.

Jill Riley: And even the redesign for me isn't the ridiculous part. It's been kind of the very, like, I didn't know that we had such Minnesota State Flag enthusiasts within the state. I had no idea! I just haven't given it — I haven't given enough thought. So it's on me.

Lizz Winstead: I'm not a flag person. You know, I just am not out waving my flag. Like that's never been — because I'm always challenged by...  What flags represent is this, to me, this institutional like support, and I am always calling BS on the institutions that run us, right? And so it's like, that flag cannot symbolize, like, "Look at our great flag!" and songs about flags. And it's like, you know, sometimes people do horrible things in the name of a flag. Turns out I have watched it happen.

Jill Riley: In history.

Lizz Winstead: In history.

Jill Riley: You are correct in that.

Lizz Winstead: And so I'm like, always, like, "You should be skeptics of people who are putting that flag up as no-matter-what, ride-or-die symbol."

Jill Riley: I think it'll look OK on a T-shirt, though.

Lizz Winstead: It'll be fine.

Jill Riley: This is like harmless on a T-shirt.

Lizz Winstead: It's fine.

Jill Riley: As we say...

Lizz Winstead: "The Minnesota State Flag, it's fine."

Jill Riley: How much more of that have you been saying since you've been back?

Lizz Winstead: It's fine.

Jill Riley: No, it's fine.

Lizz Winstead: It's fine.

Jill Riley: And not in a passive aggressive way, but it's just fine.

Lizz Winstead: No, not at all. I feel like everything's fine. We're doing great. It's fine. I mean, it's honestly, since I've got the house here, I have discovered something that I have not been exposed to in my history of being alive, and that is NextDoor.

Jill Riley: Oh, the app.

Lizz Winstead: Which is some scary... sometimes it feels like it might just be a racist Lost and Found, where people are like, there's always some questionable human in a neighborhood. And there's always, "And they have my thing." It's like, "That's a person who is collecting your garbage. They're supposed to be there, and they're picking up your can to empty it. So maybe don't sound the alarm on NextDoor." But it's always like, "Has anybody else seen a person who is walking around the neighborhood who I'm not sure is supposed to be in my neighborhood." I'm like, "Oh, man, this is some..."  "There's cats who are not ours who are out galavanting in the neighborhood and they're killing the rabbits."

Jill Riley: I dabbled in NextDoor and then I had to leave. I had to leave. 

Lizz Winstead: Get out. Get out. It is like some propaganda of like, wild neighborhood conspiracy theories that like, we get enough of that. Do we need to micro-conspiracy theorize? I don't.

Jill Riley: I like to try to nail down what house. Like I think, "Oh, it's that lady over there that posted that."

Lizz Winstead: Oh, yeah, that lady over there, for sure. 

Jill Riley: And then I had to get out of there. Because it was starting to affect me a little bit.

Lizz Winstead: Yeah. And now that we've legalized weed, you're gonna have like people who are just like dreaming up some really wild conspiracy theories. And I'm kind of, then I'm going to return to NextDoor.

Jill Riley: That happened this year, too!

Lizz Winstead: Yeah.

Jill Riley: How could I forget?

Lizz Winstead: How could you forget? In fact, I'll come back on, because I just may or may not be having my own edibles line here in the state of Minnesota.

Jill Riley: Well, you heard it right here. All right, more to come on that. More to come. Lizz Winstead, "2023andMe," that's the name of the show going on this weekend. Two shows. It's an annual event. It's a breakdown, a look back of what the heck happened in the year 2023. The Parkway Theater in Minneapolis, two nights, and you know what? We have the details at our gig list, at our concert calendar and event calendar at thecurrent.org. You can also go to the Parkway Theater website. Lizz, it's just great to see you.

Lizz Winstead: Always fun to be here and try to not break FCC rules. It's always a goal.

 Jill Riley: You did well.

Lizz Winstead: Thank you!

Jill Riley: You did well. This song, I feel like I play this song every year when you come by because the message of it, it just never gets old, that Mountain Goats song, "This Year." It just, for me, it does not get old.

Lizz Winstead: Never.

Jill Riley: And it's about this time of year where I think at least I need it. So I hope it does a little something for you, too as you are listening — not the band U2. Bono's fine. He's going to make it through this year.

Lizz Winstead: He's doing great.

Jill Riley: Las Vegas. Big year for Bono. Lizz, take care. Thanks again for coming by.