Here’s how she describes herself: “Comedian. Writer. Producer. Troublemaker.” Here’s a bit more: She’s the co-creator and former head writer of “The Daily Show”; a cofounder of Air America Radio, which is now defunct, but a cool thing to have been involved with nonetheless; and the author of a new book, “Lizz Free or Die.” Winstead was at the Brookline Booksmith on Sunday.
‘The political satirist usually votes against their own interests, but . . . Whoever’s president I’m not going to be short on material.’
Q. From a comedic perspective, who are you rooting for — Obama or Romney?
A. The political satirist usually votes against their own interests, but the bottom line is that it doesn’t really matter. We’ve got a deeply flawed political system with an insane overreaching extremist element, with a Supreme Court that is completely loony. We live in a nation where corporations are people. Whoever’s president I’m not going to be short on material.
Q. Being the youngest child in a big Catholic family seems like a good career move. You’re the youngest of five. Stephen Colbert is the youngest of 11. Is making jokes a coping mechanism?
A. It’s part coping and part the desire to be someplace — on stage —
Q. What does a satirist do all day?
A. I do a lot of reading of news so I can be smarter, and I do a lot of watching TV news so I can know why Americans aren’t very smart. Then I can point out the hypocrisy of politicians or the media. Then I throw it up on Twitter. I use Twitter and Facebook to try out material. If I get 50 likes and 25 re-tweets, and it has to be pretty much instantaneous, so if feels like you’re laughing at my joke, then I put it in my act.
Q. What’s with people who think they’re funny but they’re not?
A. I often wonder who told them they were funny. Clearly someone must have. [But] on some level that person will somehow also know they’re not funny. And they can be kind of rude, and treat a comedian like, “Who ever told you you were funny?” It’s like my success, or another comedian’s success, has been what’s preventing them from getting their just due. It’s a weird psychological mechanism the unfunny have.
Q. I was surprised to learn you played a lot of comedy clubs in Boston early on. Why here?
A. My roommate from college was Michele Norris [now the host of “All Things Considered” on National Public Radio]. She did an internship at WGBH, and I came out to drive her back to Minnesota with all of her stuff. She called some comedy clubs to get me to do some open mike nights, and I made friends with the whole comedy community. I started working at Stitches, Play It Again Sam’s, and the Comedy Connection.
Q. What are Bostonians like, from a comedian’s perspective?
A. Bostonians love storytelling — they’re very Midwestern in that way. Denis Leary, Dana Gould, Lenny Clarke — they’re great storytellers
Q. Not like you haven’t already done enough — you’re on a book tour right now —
A. I just got a column in the Guardian, starting in July. I’ll write about politics and pop culture once a week. We’ll see what the book tour opens up. I’m the kind of person who doesn’t plan. Opportunities present themselves to me. That’s how my whole life has been pretty much. I’ve been lucky.