Left Laughing

For a dyed-in-the-wool feminist, Lizz Winstead [1] is a helluva kingmaker.

Tune in to late-night television and you’re likely to find a show whose male host owes his stardom — and seven-figure salary — to her. As cocreator and former head writer of “The Daily Show,” where she worked from 1996 to 1998, Winstead helped launch the meteoric careers of Jon Stewart, Stephen Colbert, Lewis Black and much of Comedy Central’s fake news team. She also helped Jimmy Kimmel with his pilot for “The Man Show,” a precursor to ABC’s “Jimmy Kimmel Live.”

In 2003, Winstead cofounded the liberal talk-radio network Air America. Though now defunct, it introduced the nation to MSNBC’s Rachel Maddow and, arguably, convinced Minnesotans to take Al Franken seriously enough to elect him to the U.S. Senate.

But Winstead isn’t just a behind-the-scenes writing and producing genius. For years she’s done gobs of standup specials of her own, appeared on TV and contributed to the Huffington Post [2]. She can riff on a range of subjects, from self-described “fool for Christ” Michele Bachmann to solar-powered vibrators. This weekend, Winstead brings her razor-sharp political skewers to Burlington’s FlynnSpace for two shows titled simply “An Evening With Lizz Winstead.”

Despite her platinum-plated comedic cred, Winstead has spent the last few years working full time — for no pay — with a web-based comedy troupe called Shoot the Messenger [3]. Together, they produce the satirical “Wake Up World,” an online spoof that bills itself as “America’s only six-hour morning show.”

Winstead, the show’s creator, stars as host Hope Jean Paul. With cohost Davis Miles (Baron Vaughn) and busty weather chick Emily Rackcheck (Darbi Worley), she chit-chats over coffee about genital warts and exciting new products such as “MyNecology,” the at-home pelvic-exam kit. The breaks feature commercials for fake businesses such as an online service called freetorturereport.com and “Darfour Seasons,” a five-star resort in Sudan that hosts celebrities traveling to Africa for photo ops and adoptive babies.

Winstead, 48, grew up in Minneapolis. Her mother, a decoder in Navy intelligence during World War II, met Winstead’s father in Washington, D.C., while he was recovering from malaria he had contracted at Guadalcanal. Winstead was the youngest of five siblings in her “crazy Catholic family,” all of whom “walked, ran or sprinted away from the Catholic Church,” she says.

Today, Winstead is single, lives alone in Brooklyn and shares her bed with two four-legged companions, Buddy and Edie, both rescue dogs. The former has appeared in several “Wake Up World” sketches, including one where he appeared as “Lumpy the cancer-sniffing dog.”

Winstead, who loves to cook, hosts a weekly Sunday dinner at her house for Shoot the Messenger’s cast and crew. That is, when the troupe’s members aren’t on the road pursuing their own budding careers, which they owe largely to Winstead’s Midas touch.

Other fun facts about Lizz: Growing up as a feminist, she loved Barbie — not as a possessor of preposterous body proportions, but as a positive role model: “She’s a single woman with a house and a car who did whatever she wanted,” Winstead says.

Winstead is also a yoga addict, is deadly at Scrabble (average score: 375), loves sex but doesn’t want kids and doubts she’ll ever marry. Another thing she adores, she says, is performing in small, progressive cities such as Burlington, Asheville, N.C., and Missoula, Mont., where many people think much the way she does. She’s insanely friendly and generous with her time. When Winstead took a break from her moment of Zen to talk with Seven Days, the phone call lasted more than an hour.

SEVEN DAYS: Did you grow up in a political household?
LIZZ WINSTEAD: I did. It was weird, because my parents were both archconservatives ... And, because I’m youngest of five — I’m 48, and my oldest sister is 62 — the fights we’d have during the Vietnam War and Nixon ... were fast and furious. My three sisters range from Democrat to radical. My brother is an independent Republican who’s now the mayor of Bloomington, Minn. We call him “the Mayor of the Mall” because he’s the mayor of [the town] where the Mall of America is.

SD: How’d you get started in comedy?
LW: When I was in college [at the University of Minnesota], I was more the class cynic than the class clown. And so somebody dared me to go to an open mic when I was in my junior year ... I did it on sheer adrenaline. I did OK.

And then I got cocky, and I did it a second time and bombed! Like, a thousand deaths. And so I was, like, “OK, now I’m 50-50” ... So, the next time I got up on stage, I did not bomb but did not kill. So then my curiosity was piqued. And I kept doing it to see where I was, and before I knew it, I was developing a routine ... And then I dropped out of college.

SD: Is it true you once fell asleep during your act?
LW: Yes. I have narcolepsy, and I take a pill every day for it ... I’ve fallen asleep at very inopportune moments, anywhere from standup comedy to sex, which isn’t very complimentary to your partner.

SD: That’s probably more common than you’d think.
LW: Yeah, exactly! Only they don’t have anything to blame it on. I can actually cry narcolepsy, but the relationship ends no matter what.

SD: Besides your dog, have you gotten other family members into show biz?
LW: I had my parents on “The Daily Show” the first year. They did little bumpers [brief announcements between commercial breaks].

I’m a big fan of “Jeopardy!” but because I was working 18-hour days, I couldn’t watch it ... It was in syndication and on in Minneapolis early in the day. So, I would have my mom watch “Jeopardy,” and then she would call and tell me the Final Jeopardy! [question], and we’d put the bumper in the show. I thought she’d just give me the answer, and we’d post it as is ...

But my mother’s rantings on the answering machine were funnier than her just doing Final Jeopardy. She’d be, like, “Uh, this Russian person wrote a book about a ‘goo-lag,’ and I can’t possibly tell you how to write his name out, but it’s Aleksandr and then a whole long name with an S.” We’d have her asking the Final Jeopardy question in the most convoluted way. It was hilarious.

SD: How’d that work out?
LW: “Jeopardy!” gave us a cease and desist [order] and named my mom in it, so we had to call it something else ... And my dad preempted it by swearing at Alex Trebek every week, saying, “How dare you threaten my wife! Here’s the trivia question.” ... So they became little tiny celebrities in Minneapolis, and they were very excited. Then I had to fire them.

SD: Why?
LW: They were on for a year, and the segment ran its course ... Having to tell your parents that they can no longer be on television is pretty awful. “What did we do?” “Nothing! That’s how TV works!”

SD: You lost your dad in 2006. Is your mom still alive?
LW: She is. I do a lot in my show about my mother and me, just trying to have a conversation while she’s got FOX News blaring 24/7 in the retirement home.

I know, it’s nuts ... One of my favorite things she said to me recently, she was talking about [how] — as you can only imagine at an assisted-living facility — the dinner tables change often, because people “go away.” So, she was seated with a new woman who apparently is a Democrat. And she said, “Lizz, she’s awful! I’d rather sit with the Alzheimer’s people than the Democrats.” To which I replied, “What’s the difference?”

SD: So many political satirists are on the left. Have you worked with any on the right?
LW: I have. I can’t say that I’ve seen very many, though, with the exception of Dennis Miller ... But I don’t understand how, after 9/11, you become a Tea Party person.

But ... your party affiliation means nothing to me. If you are given by the people the gift of power and you choose to abuse it, then you are my personal target as a comedian. I don’t care if you’re a Democrat or a Republican. And, right now, it’s everybody. When corporations are people, all bets are off.

SD: Have you ever seen good conservative satire?
LW: When you do see those kinds of things, they tend to fall flat. FOX tried to do their version of “The Daily Show” a couple of years ago, and the material was so stale and boring. They were doing ACLU jokes and that kind of thing ... What’s frustrating to me about the right is that there’s never an acknowledgment when the thing they were railing about has been proved to be inaccurate, like ACORN.

SD: It’s like what Stephen Colbert said about George W. Bush at the 2006 White House Correspondents’ dinner: “He believes the same thing on Wednesday that he did on Monday no matter what happened Tuesday.”
LW: That was such a fascinating thing. Many people forget that that was the first time George Bush had been held to hear his record and wasn’t able to leave. He wasn’t able to orchestrate the crowd like he’d been doing in the rallies ... And the media had to hear it, as well.

And so it was very interesting, because people who watched that thought it was really funny, but the press was, like, “Stephen Colbert bombed.” No, you get to say that because you’re a little mad that he called you out on how you handled the war and all that other stuff. So, everyone tried to form this meme that Stephen didn’t do well, when he was fantastic.

SD: Do the people interviewed in news segments always know it’s for “The Daily Show”?
LW: They do ... It always amazed us as well that people would go on camera. But that says so much about people, that they’d rather be on television in any way, shape or form than ... understand how they may be presented ... When you’re talking about “The Daily Show” ... the guest is almost never going to be the smartest person in the room. This is a sharp group of people who really know their stuff and really know how to craft things in a way that, basically, allows someone to reveal who they are just by letting them talk.

SD: What do you see as your primary job? Making people laugh? Informing them? Speaking truth to power?
LW: I think it’s a combination of all those things. I’m not an expert, but I am an informed citizen. First and foremost, I’m a comedian. Through my comedy, if I’m going to talk about the news of the day or give insights on where I see hypocrisy, I have to look at all sides of an issue and then figure out where the hypocrisy lies ...

With media that go unchecked, so that sometimes blatant untruths are thrown out there, I think it’s really fun to gather people together so you know you’re not alone when you hear crazy shit ... So when Obama says, “We’ve seen what happens when administrations hire the very corporate interests who set up that policy, and that’s got to stop.” Hello? Did you just say that? Really? Tim Geithner? Ken Salazar? You hear these things, and instead of people injuring themselves by hitting their heads against walls, I’d like to provide the cushion.

SD: As 24-hour cable news shows and morning talk shows get more surreal by the day, does that make your job easier or harder?
LW: It makes my job sadder. It makes my job easier because I do a lot about the media anyway ... I find the media are as complicit in the nation’s biggest problems as the direct people in the deal.

A lot of times people will talk ... about FOX and Beck and Rush. That’s the WWE of cable news: the big, loud stuff. But sometimes I feel the more dangerous thing is when you have these talking-head commentators who don’t have a command of the facts, and they’re not journalists. So, when someone comes on [their show], they don’t have the facts or resources to ask a follow-up question or challenge them ... Sometimes I think I should just vote for Republicans, because they keep me in business.

SD: The Dems are no great shakes, either.
LW: When Obama won, I was interviewed by a lot of people who said, “So, what are you going to do? Your guy won.”

I thought, Um, he’s a politician ... When people said that to me, there was a tinge of racism in that statement. Because what I was hearing was, “Hey, there’s a black president. Are you going to make black jokes?”

Why would I make black jokes? I don’t care that he’s black. He’s a politician who takes money from lobbyists ... When you’re expanding wiretapping and you haven’t closed down Gitmo, and you’ve escalated the war in Afghanistan and you received the Nobel Prize on the same day, there’s a lot of fodder about you.

SD: What’s up with “Wake Up World”?
LW: We’re desperately trying to get that on [TV] as a show ... But I signed on to do a book this year ... and doing my standup. We shot a little pilot, and I have to go out to L.A. and really try to sell it. The problem is, I have to go out to L.A.! ... But it’s a really fun show to do, and I think the targets are fun ... There’s something like 21 hours of morning shows every day, if you include Kathie Lee [Gifford], “The View” and all that.

SD: That’s got to be painful for you to watch.
LW: But you have to! And the interesting part is, on the major networks, that money comes out of the news division. The “Today” show may be the most highly funded show coming out of NBC News. When your show has its fourth hour and the fourth hour involves Kathie Lee, do you really need that fourth hour? ... They may do a story on the war in Iraq that’s three and a half minutes. But then they’ll do a story about the healthiest cocktails. Or, “Does this jewelry make my butt look fat?” I don’t know what those shows’ priorities are, but it’s like theater of the absurd. It’s Kabuki.

SD: I understand you’re a foodie.
LW: Yeah, I’m a big foodie. I’m a cook, I watch foodie shows, I love farmers markets. I also love junk. I never had it as a kid. My mother was that woman who cooked everything. And it wasn’t all healthy, trust me. There was plenty of tuna casserole and all that. But we never had bad food. It was too expensive. So when I got into college, I tasted McDonald’s for the first time. I still get a hankering for it. About once a year I’ll get their French fries and eat ’em in my underwear like a psycho drug addict. It’s like Requiem for a French Fry in my apartment. It’s pretty bad.

SD: Tell me about your Burlington show.
LW: I will be talking about the oil spill and the financial crisis. I will be talking about my mother and her relationship to me and politics and how that affects me, and my love of animals ... But there’s so much that I don’t even know I’ll be talking about because it hasn’t happened yet.

SD: You write your show that week?
LW: It’s kind of fun. I arrange two music stands on stage where I have notes divided up so I can engage with the audience the whole time. I have a set of notes so that I can be writing up till the very last second when I’m on stage.

SD: Are you a workaholic?
LW: You know ... initially I wanted to be a history professor, so I think I would be engaged and drinking this stuff up anyway ...

A lot of people have busy lives and don’t have the luxury to watch things unfold, so they rely on, sadly, “The Daily Show” and Bill Maher and alternative media to get this stuff. So, if I can provide a little insight and information to people who are too busy to get it all, I’m happy to do it.