Lizz Winstead, the subject of the following Q&A, is headlining five shows over two nights at the Comedy Works (click here for details), but she’s hardly the average standup comic. She co-created The Daily Show, one of the most influential comedy programs of the past decade-plus, serving as the production’s head writer for two years – and while she left during the Craig Kilborn era, prior to the period when Jon Stewart pointed the anchor chair in an entirely new (and better) direction, her influence lingers. For one thing, she’s a former Stewart collaborator, having produced a talk show he hosted before he started the Daily grind. For another, she hired Stephen Colbert, now the host of his own night-live fave, The Colbert Report, not to mention often-riotous ranter Lewis Black, who remains a regular.
The conversation begins with Winstead talking about Shoot the Messenger, a once-a-week live production currently running in New York City, which satirizes morning television – a subject ripe for ridicule. Then, after touching on her standup plans, she shares insights about The Daily Show and Air America radio, another project that she helped launch, and one whose financial struggles strike her as resolutely unsurprising. Then, after confirming that she plans to bring Shoot the Messenger to Minneapolis for the Republican National Convention, she floats the possibility of coming to Denver when the Dems hit town, if a local theater would be willing to pick up the tab.
Will an impresario out there hear her plea?
Westword (Michael Roberts): For the uninitiated, how would you describe Shoot the Messenger?
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Lizz Winstead: I guess I would describe the show as, if Colbert had decided to do a satire of all the morning shows that are on. It’s Colbert in tone – not in the patriotic, rah-rah tone he does Colbert, but in the way it’s a cast of characters. They’re a team on this morning show, and the morning show is sort of a hybrid of everything from the Today show and Good Morning America to Regis and Kelly to The View, on a fictitious network. Basically, all of the guests are anchors on other shows on this hideously crappy network, so the only information they ever disseminate is from other people on their network.
WW: I’m sure the morning shows have given you plenty of grist for the mill given the way they’ve evolved over the past few years…
LW: Well, evolution is an interesting term to use…
WW: Maybe “devolution” is better.
LW: Well, I’ve always wondered why you need a four-hour morning show. If somehow you have a show and you decide your fourth hour will be helped by the hiring of Kathy Lee Gifford? I’m not sure the visionaries are at work here. I think they get up to early and they make decisions that don’t always seem like the best ones.
WW: I’ll bet you’re not complaining, though.
LW: Let me tell you: Sometimes I feel like they’re in business to keep me in business (laughs).
WW: Did the idea for Shoot the Messenger come to you simply from watching this stuff and wondering what on earth is going on here?
LW: Yeah. I’ve sort of spent my career doing political satire and satirizing the media. For the past ten years anyway, certainly. And when I started getting animals, I started getting up early and finding out what these shows were about, because your dogs want to go out and that’s what happens. And I counted up the number of hours on television that are sort of providing this morning type of chat, and it’s 23 hours. There’s 23 hours of morning-show programming if you include all those shows we mentioned earlier.
(A dog begins barking frantically.)
LW: Oh! I might yell “shut up” or “be quiet,” but it’s not at you.
WW: There’s the animal you just alluded to.
LW: Yes, the aforementioned animals, who when you live in an apartment in New York that happens to be right on Broadway, there’s always a noise that makes them jump up. But anyway, I thought, so, this is a lot of programming and what are they saying? So I started turning it on between seven and eight, when I figured regular folks were getting ready for work and they were turning on their TV to get some information, just to see what an average person is getting in the morning. And it’s astounding. There’s as much emphasis on getting the right bra for your hairstyle as there is about the immigration problem or the war or health issues. So it’s kind of like, how can they have these priorities? I’d be watching, and they’d be like, “Coming up: Cajun cooking and the Iraqi death toll!” Wow: like, no producer thought, maybe we should break those out, and maybe the same perky voice shouldn’t be telling us about the cooking and the Iraqi death toll. I thought, this is insane. It’s really ripe for parody. It’s a lot of fun.
WW: Did you envision this concept originally for television? Or did you always see it as a live production?
LW: I call it a living, breathing pilot. We do it every Monday night live, and we also have a website that supports all the episodes. So anywhere you live, you can go to our website, you can see our Monday night show. We usually have it up by Wednesday night.
WW: Is the address ShootTheMessenger.com?
LW: Don’t go there. That is something entirely else. It has to do with someone’s spirituality. So we had to add the “NYC.” It’s ShootTheMessengerNYC.com. And the goal is either to have a fully fleshed-out, viable website and live show or to have it be a TV show. That’s the plan. We live in an age where TV, it’s tough to get something on, and you do a pilot and you have one shot. And we thought, let’s bring it to a theater. Let’s bring a live TV show to a theater, broadcast it on the web, and let people come down and see what we’re doing. And it’s been really fun.
WW: Has it been difficult to convince people to devote themselves to this kind of project on a volunteer basis?
LW: You know, it hasn’t. If you look at the shows people like, whether it’s Jon Stewart or Bill Maher or Colbert or let’s say this, for example: The people who work on these shows and the reasons shows like this are successful, I think, is because anybody working on any of these shows would do it for free anyway. It comes from your core, from your belly, so being able to work on a production is really great. And it also helps people. When you get young, interesting writers who are just starting out in the business, or they’ve only been in it for a few years, they’re learning a bunch of really cool skills – learning really what it means to be in a writing room, what it feels like to have ideas turned down not because they’re not funny, but because they don’t live in the tone of the show. It teaches them to write for an entity, not for themselves. And it also gives them tape to put on their reels. So it’s kind of great in a lot of senses.
WW: The New York Times recently profiled Shoot the Messenger. Has that led to your phone ringing more often?
LW: Yes it has. We’d been doing the show sort of secretly, for a lack of a better way of saying it – just inviting our friends and having this grassroots kind of audience develop, because we were trying to figure out who we were onstage, so that we could really get it to a place where we felt like, “Let’s start bringing people down.” And after six or eight months, we did that. So we’re really excited that the Times did this profile and Time Out New York did a profile. People are sort of coming and calling, and it’s really fun, and they’re really liking it. And the part of the show we haven’t talked about is the second half, which is a completely different ballgame. It’s just me sitting down and doing this kind of Charlie Rose on cracker interview with people in the media who might not necessarily see: authors, comedians, independent journalists. And we do this one-on-one interview using Q&A from the audience. It’s really fun.
WW: Obviously, this show is too big to put on at a comedy club in its entirety. So will you be doing a variation on it, or more of a standup routine.
LW: I’ll be doing more of my standup act. It’s fun. I’m pretty political, and it’s a really fun time to be talking about politics. I’ll be doing a lot of stuff that’s really current and up-to-the-minute. It’s normally what I do when I go out on the road. Talking a lot about the candidates. You guys have got some fun stuff in Denver to talk about, too. Marilyn Musgrave, I do enjoy her very much.
WW: Don’t we all.
LW: She’s been a font of information and comedy for me for a couple of years now, and what’s great about coming to Denver is I don’t have to explain who she is. With other audiences, I have to give them a little primer. Here I can launch right in.
WW: And if, for example, on the morning of your appearance here, an Eliot Spitzer-type event takes place, do you drop everything and start coming up with your take?
LW: Absolutely. If something big breaks, the Denver audiences, I will guarantee that they’ll hear the latest breaking news in my shows. That’s what’s fun. It’s kind of like getting a jumpstart on SNL. It’s like, “We’re going to be able to laugh and have some catharsis before anybody else.” So that’s the plan.
WW: Obviously, you’re well-known for co-creating The Daily Show, and the program’s gone through changes aplenty since you were the head writer there. But how close is what people watch now on a nightly basis to your original conception of the show?
LW: Well, the format is almost identical – the way it’s set up. And I’m glad Jon [Stewart] took it in the direction he did, and I knew that he would. Basically, what was great is, when we first launched, we would always have constant philosophical debates about how political the show should be. The network wanted it to be a little more of a hybrid of entertainment and politics, and I always thought politics was the way to go, because if you’re going to satirize, it’s nice to have big, powerful people to satirize. Sometimes I think when people veer into satirizing entertainment figures and stuff like that, it just gets kind of mean and cruel. Like Britney Spears, I find her to be sort of a tragic figure. I don’t really have anything to say about her because I feel bad for her. She’s a mess. But they thought, “People don’t care about politics. They don’t want to hear that much about it.” And I was like, “I disagree.” So we found a balance there. And then when Jon came in, I think he was more along the lines of the philosophy that I had. He wanted to take it to its full, upright and locked position, if you will, following politics. And as we know, he’s made this amazing creation.
WW: You worked with him on his original talk show that predated The Daily Show. Did you see that side of him then? Or did it surprise you?
LW: It didn’t surprise me at all. Jon and I have worked on a couple of things. We wrote a pilot together. We hosted Short Attention Span Theater together on Comedy Central. He asked me to come back to The Daily Show a couple of times when he took over, and I was like, “You’ve got this covered, my friend. I’m going to try to do other things.” And then I launched Air America radio. I wanted to bring comedy and social satire to other kinds of venues and arenas. So that was the direction I chose to take. But I wasn’t surprised at what Jon did at all. His comedy has always been infused with political and social satire. He’s always been somebody who loved taking on the powerful. It didn’t matter. It’s really not about whether you’re a Republican or a Democrat. It’s about taking on the big guys and how they’re using their power. If they’re using it for evil, they’re going to get hit.
WW: You mentioned Stephen Colbert. Were you part of the team that brought him and Lewis Black aboard?
LW: Yes, indeed. I am definitely that team. Lewis and I have been really, really dear friends, and he was the first call I made when the show went up. I said, “Dude, do you want to do a weekly segment where you just rant about whatever’s on your mind,” and he said, “Yes.” And Stephen also. Oddly enough, we saw Stephen – he was doing bits on Good Morning America. He was kind of doing funny stuff on there.
WW: Do you take pride in what’s happened with those two, as well as with the show as a whole?
LW: Totally. What’s great about it is, it reinforces that my instincts are pretty good. These people are geniuses all on their own, and I happened to see them and go, “Wow. I think what you do would fit really well with what I’m doing.” When you see people now coming up, I feel like I can get a pretty good sense of picking talent, which makes me feel pretty good. When your instincts have paid off, it’s good, because you don’t have to do a whole lot of second guessing.
WW: You mentioned Air America, and that organization has had some financial struggles…
LW: You think?
WW: I was trying to sneak up on this topic, but apparently not too slyly. Any frustration or disappointment about the way that project has gone?
LW: Clearly, it got off on the weirdest footing imaginable with its finances. You always hope for different voices being out there in the universe, so people can listen to different points of view and make their own decisions about what they think. It’s sad to me that there was that crazy wave of corporate weirdness. But the fact of the matter is, going back to instincts, the first person I hired on Air America was Rachel Maddow. We hosted a show there for a little over a year with Chuck D, and Rachel is the biggest breakout star of the network, and now she’s on MSNBC every night. If nothing else happens, I am so completely excited that the world is now exposed to this really amazing, funny, insightful brain. So that’s really cool.
WW: In terms of the challenges Air America had, did you underestimate how difficult it would be to put a dent in the monolithic, right-wing nature of talk radio? Or did you realize all along that this was a gargantuan task?
LW: Well, what happened was, when we came onboard, the CEO and the people getting the money and stuff already had a vision in place. And their vision was doing eighteen hours of original programming launching a network. We couldn’t really talk them out of that. So instead of developing two or three really good shows and trying to syndicate some shows, so it could be a manageable thing, there was a daunting task that was insane. And there wasn’t, myself included, a whole lot of radio people involved in the bigger picture stuff. So we kept saying, “Can we get some radio people to be our bosses? Because that’d be awesome. I’d really like to learn about radio, because I believe we’re going to be on the radio.” And so I think part of the creativity and the energy and a lot of the good stuff that came from a lot of us trying to do it could only go so far, because we didn’t really have anybody in charge with any kind of radio background to make some good decisions. So that was a bummer. But really good talent came out of that place, and I feel really excited to see Laura Flanders, and to see Marc Maron, who became a really great radio host, and Rachel, and Ed Schultz is now syndicated and on Air America stations, and I think he’s probably the best in the business in progressive talk. So it’s good.
WW: The New York Times article mentioned that you plan to bring Shoot the Messenger to Minneapolis for the Republican National Convention…
LW: I’m definitely doing that.
WW: Well, we’ve got a convention here, too…
LW: I know!
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WW: …and I was wondering if your upcoming appearance might be a way of testing the waters to see if it makes sense to bring the show our way.
LW: Well, I’ll tell you what. If some fantastic theater wanted to pay to bring our production there, it’d be great. Part of the things we’re doing that’s so lucky is, we’re doing this crazy Shoot the Messenger show – we have a 22-person staff of volunteers, and it’s really an elaborate show. We have more content than Saturday Night Live does in our Monday show. It’s nuts. But I’m from Minneapolis, and I have the good fortune of being able to bring the team there, house them with family and friends, and stuff like that. So that’s why Minneapolis works so well. But sadly, I don’t have that in Denver. So if people reading this think that we sound so lovely that they’d love to bring us to Denver, guess what? We’d love to go.
WW: We’ll put out the word.
LW: Put out the word. That’d be awesome. It’s not for lack of want, trust me. We would die to come to Denver.