News & Features » News

To the left on your radio dial



Lizz Winstead was having brunch in Manhattan's Noho Star on Jan. 4, wearing a Hüsker Dü T-shirt. Slight and fierce, with a tinge of gray at the roots of her curly, brownish-blond hair, Winstead was talking about her career in comedy and the prospects for Central Air, the soon-to-debut, left-wing talk-radio network for which she's directing the entertainment programming.

The course of both topics, it seems, have been altered by the specter of a certain sex act.

"Clinton's blow job was the worst thing to happen to political comedy ever," Winstead says emphatically. "Because it just became a blow job joke. It didn't become satire; it wasn't about his policies. There was a lot to mock the right about that the left didn't get the opportunity to do."

The other fateful fellatio-related incident is the reason Winstead left "The Daily Show," which she co-created for Comedy Central with Madeline Smithberg in 1995. The show was the crowning achievement of a career that had started in the grueling trenches of stand-up comedy. While Winstead served as one of the show's chief writers, there was growing friction with the then-host, Craig Kilborn. The final straw for Winstead was an interview Kilborn gave to Esquire magazine for the January 1998 issue. "There are a lot of bitches on the staff, and, hey, they're emotional people. You can print that!" he said. "You know how women are -- they overreact. It's not really a big deal. And to be honest, Lizz does find me very attractive. If I wanted her to blow me, she would."

Kilborn, who declined through a spokesman to comment for this article, was suspended for a week.

If Kilborn's blow job line -- he later said he meant it "as a joke" -- impelled Winstead to leave her beloved "Daily Show," it also freed her up to find other ways to resuscitate left-leaning political comedy. Enter Central Air, scheduled to hit the airwaves as early as March. Its masterminds say it will be tailored to appeal to people with politics who crave Rush Limbaugh-style bite. Less earnest than National Public Radio and not as strident or suffused with the victim/oppressor paradigm as Pacifica, it will bring a populist, late-night-television sensibility to radio.

Winstead has a lot on the line: Not only will she mastermind the network's entertainment element, she will host her own three-hour show, which will air Monday through Friday from 9 a.m. to noon. She will have a co-host, whom she has not yet chosen. The show will be a mixture of her own riffs, co-host banter and reported pieces. "It won't be completely scripted," Winstead says.

Each show, she explains, will have "universal comedy and then branding elements," like the Top 10 List on "The Late Show with David Letterman." "We'll do legitimate newscasts, really diving into the day's news, and we may have a recap that's more satirical."

Left-wing conspiracy

Most programming will be produced in the network's midtown Manhattan studio, which they've been occupying since December. The New York-generated content will be supplemented by material out of studios in Los Angeles and Washington, D.C. While the network has yet to finalize its staff, this much is set: When it launches in March or April, it will broadcast 14 to 18 hours a day, seven days a week, on stations it is buying -- or whose airtime it will lease -- in major cities like New York, Los Angeles, San Francisco, Philadelphia, Miami, Pittsburgh and Boston, says Mark Walsh, the chief executive officer of Progress Media, which he co-founded and which is the parent company of Central Air. "In division, there's a media opportunity," Mr. Walsh continues. "In a divided nation, at least there are opinions, information which takes a side."

A former AOL executive, onetime news anchor and HBO executive, Walsh was named in 2002 as the first-ever technology adviser to the Democratic National Committee. The network, however, will not be formally affiliated with the D.N.C. Nor is it the same fledgling liberal-media project that Vice President Gore was working on. Progress Media has "no official business relationship" with Mr. Gore, Mr. Walsh says. "I love how the right seems to drop that this is a vast left-wing conspiracy," he adds.

Walsh wouldn't say which stations they were buying, but says they expect to sign the paperwork by next month. "They're full-power stations with good to very good broadcast footprints," he says. The main investor is Evan Cohen, a New York-based venture capitalist who's worked in radio and advertising in the Pacific Rim. Walsh is also an investor.

A host has not yet been chosen for the all-important morning slot, from 6 a.m. to 9 a.m., Eastern Standard Time. Central Air recently signed with Al Franken, whom they are hoping will take the mike from noon to 3 p.m. -- meaning he'll go head-to-head with Rush Limbaugh. After that comes a show hosted by A. Whitney Brown, who collaborated with Winstead on "The Daily Show" in the mid-'90s. Talks are also going on with Janeane Garofalo for a late-night show. Martin Kaplan, an academic and former screenwriter and Mondale speechwriter, will discuss the media from 7 p.m. to 8 p.m.

Every host will have a partner, Winstead says: "No monologues. We feel people should be kept in check all the time." They haven't locked in any co-hosts yet, but "if this plays out the way we think, there will be a woman on every show" as one of the hosts, Winstead says. "That's important."

Progress will also have a lot of women running the show, chief among them Shelley Lewis, a former executive producer of CNN's "American Morning," who will oversee the network's news division.

As for the short, satirical features that, in Winstead's vision, will make Central Air more akin to late-night TV than to any existing radio network, details are still sketchy. A weekly 90-second feature called "The Red and the Blue States," "on each state and how it became what it is today," is planned, as are satirical profiles of "people in the news," according to Winstead.

"The Daily Show" looms large over the enterprise. Jon Stewart is a success because, Walsh says, "he does both sides of the fence. His whole point is making fun of stupidity." While Winstead says they'd like to share the "Daily Show" audience, she hopes they will weigh in more forcefully on issues than Stewart does. "'The Daily Show' is a specific genre: comedy wall-to-wall," she says. Central Air will be a news network, with satire interspersed throughout its coverage. "We're taking a stand and having an opinion," Winstead says. "I don't think I feel comfortable sucking up to Henry Kissinger or promoting his book" -- a dig at Stewart. "Someone else on the network may," she adds.

Popular populism

Progress Media will have a decidedly populist take. "Absolutely!" says Winstead, who says she turns off NPR "when there's a presupposition that I know more than I know, and then I feel like I'm not in the club." She turns off Pacifica when they drone on with stories on topics like Charles Taylor. "That's relevant, and we will talk about those things," she says. But they really want to appeal to the guy "who's figuring out why his paycheck is so little and he can't make ends meet and he's working 50 hours a week and still has to get government assistance," she says. "I don't think those people are really being serviced."

While liberal, the network's target audience is "everybody that's upset or bored or tired of what is available on radio today," Walsh says. "The business answer is, we want an audience that advertisers care about," he adds. "We want to have shareholder value and create a profitable, sustainable, long-term company." The company's business plan "has us making no money for many, many months from launch," Walsh says. "We're expecting a slow trial."

Ms. Winstead will oversee and edit a stable of 10 writers, most of whom have worked with her before. A handful came from "The Daily Show," others from "Court TV," where Winstead developed "Snap Judgment," a satire of the legal system. Others come from network TV or from the Oxygen network, where Winstead developed "O2B," a spoof of women's talk shows that was pulled after one season in spite of good reviews. "I have basically hired people who are funnier than me and smarter than me, and who understand me," she says.

News whore

Asking Winstead about her political views elicits somewhat predictable lefty boilerplate. She is vehemently opposed to President Bush, tax cuts for the rich, school vouchers and the war in Iraq, not to mention Wal-Mart, "the No. 1 destroyer of American main streets." Yet she is more often than not riotously funny on specifics. The New York Times, she says, acts "like a celebrity who gets pregnant -- expounding on things everyone already knows as if they were the first to discover them." On Madeleine Albright: "What's up with that brooch? Can't she tone it down? Is she getting Dish TV on that? It's out of control."

"Lizz is a news and information whore," says comedian Sarah Silverman, Winstead's best friend. "She's like a beautiful flower that blossoms in election years. "The Daily Show" was her dream show, and now this radio project is. The programming of this network has been living, burrowing in her brain for years." Winstead and Silverman often talk politics. "We agree on almost everything," Silverman jokes. "Except that I think that the Holocaust happened."

Silverman also confirms that her friend is narcoleptic. "Did she tell you that?" Silverman asks. "She has no problem taking pills to make her stay awake. Otherwise, she's out by 9."

Winstead's condition was diagnosed about 15 years ago. Medication, she says, makes her nearly normal. "Before, I just thought I was tired all the time," she says.

Winstead is 42 and wears a lot of rings, none a wedding ring. "I reject traditional marriage. I'll never get married; I don't want kids," she says. "Having a dog is a big enough thing for me." Besides, she adds, "I can't imagine doing this and having a family."

The youngest of five kids, Winstead grew up poor in Minneapolis. Her dad, a Mississippi native, sold carpeting, and her mom stayed home and volunteered at their Catholic church. She was sent to Catholic school and lobbied for girls to be allowed as altar boys. Her parents, now in their early 80s, are "the funniest conservatives out there," she says. "Everyone was a liberal around me, except for my parents."

Her family would argue about the Vietnam War. "Someone was always having a conversation with my parents and storming from the table -- someone with beads and some sort of fringed outfit." (Her brother is the Republican mayor of Bloomington, Minn.)

It was the land of Paul Wellstone and Walter Mondale and Hubert Humphrey. She calls the late Senator Wellstone one of her heroes. "My politics are liberal from being from Minnesota. I went back last fall and there were signs up on people's lawns in Minneapolis that said, 'We will pay more taxes for a better Minnesota.' That's the kind of state it is. It's a state that I just firmly believe is always looking out for people who are disadvantaged and need some help."

When she was 16, Winstead got pregnant. An ad on a bus for free pregnancy testing led her to the Lambs of Christ. There, a woman in a white lab coat whom Ms. Winstead assumed was a doctor -- "until I realized you could work at the Lancâ?¢me counter and wear a lab coat" -- told her it was "mommy or murder." She opted for Planned Parenthood. "Someone said to me, 'What do you want for your future? Do you feel like you're ready to be a mom?' 'Well, no, I don't.'"

She had an abortion. It was 1979, and "Roe v. Wade was six years young. My mom still prays for me, God bless her."

At the University of Minnesota, she was studying to be a history professor, but 18 credits shy of graduation she left to do stand-up. She drove around the Midwest doing one-night gigs. That was 1983. "It was the Reagan era, big-time," she says. "It was 'Mourning in America,' I must sayÃ?that's an O, U, mourning."

The experience was like comedy basic training: "Half the time people like you, and half the time people hated you," she says. "It was fun to see the pulse of America. Traveling that much, I have a pretty good idea what it's like."

She took her act to Los Angeles, but "what I was offering was not what anyone was asking for," she continues. "In 1987, no one wanted to hear political comedy in L.A. It was not a money-maker." Eventually, she landed a job as the head writer on a Comedy Central show called "Women Aloud." This led to a job as a segment producer on Jon Stewart's syndicated show. Then, in 1995, came "The Daily Show," with Craig Kilborn as host. Stewart didn't take over until 1999.

After leaving "The Daily Show," Winstead moved back to Los Angeles, started a production company with her friend Brian Unger and produced shows for MTV, Oxygen and others.

When Progress Media called in August, she leapt at the chance to move back to New York. "Aside from my stand-up, it's the first time in my career I can hone a muscle I think I'm best at, which is political satire," she says.

Everybody likes beer

For all Ms. Winstead's enthusiasm and talent, the challenges she faces are considerable. Can the network find the right tone and sustain it, 18 hours a day? Will they need to aim to the far left to get listeners, yet aim to the center to get ad dollars? How will the TV-honed skills of both Ms. Winstead and Ms. Lewis, the news producer with the CNN background, make the transition to radio?

It depends on whether Winstead's dream audience -- semi-well-informed liberal populists with a sense of humor -- tunes in. "They do want to be strident and appeal to the angry left, because that's how you build a legitimate base and build out. That's how conservative talk radio started," says Brian Lehrer, host of a weekday morning call-in show on WNYC. Lehrer says he wasn't concerned about losing listeners to Central Air. Still, "they shouldn't sound like NPR if they know what's good for them. NPR is about context and depth and nuance and things like that. They want their network to be like liberal Rush Limbaugh."

Yet here's one reason why that might be difficult. Consider this statement of Walsh's: "The Republicans see everything as binary, black or white. We think the world is a little more analog: There's some gray in between the binary stances." His statement -- reductive at best and arguably false -- might just also explain why conservative radio tends to draw more listeners than liberal radio. After all, militant open-mindedness doesn't have the same pull as a visceral argument.

Democrats, Walsh acknowledges, are "reasonably criticized" for striking an "eat your vegetables" tone. "We definitely can find ourselves sinking into a lecturing, hectoring mode." Central Air will "nuggetize" news and opinions into entertaining programming. "The way that if you have a dog, you crush up the vitamin pill into the dog food."

To Winstead, Dennis Miller stopped being funny when he became conservative. "I would definitely say the right is not in any way funnier than the left because the right, especially now, is spending way too much time deteriorating the civil liberties of human beings and inserting God into all walks of our lives -- so that if liberals don't seem funny, maybe they're too busy being pissed off."

As for Ms. Winstead's own show, just who listens to the radio from 9 a.m. to noon anyway? People who don't work, or who work from home? "I don't even know, actually," Winstead says. "That's a good question."

Doesn't the network need to have a clearer idea of its demographics to sell ads? "Radio advertising is mostly local," Ms. Winstead says. "We have a president who did not get elected by a popular vote. Those numbers haven't dramatically changed. If 50 percent of the electorate didn't vote for him and feels disenfranchised, those people still buy soap, and they buy toilet paper, and they go to the local auto-parts store," she says. Besides, she adds hopefully, wrinkling her brow in an expression that is at once intensely focused and endearingly warm, "everybody likes beer!"


We welcome readers to submit letters regarding articles and content in Orlando Weekly. Letters should be a minimum of 150 words, refer to content that has appeared on Orlando Weekly, and must include the writer's full name, address, and phone number for verification purposes. No attachments will be considered. Writers of letters selected for publication will be notified via email. Letters may be edited and shortened for space.

Email us at [email protected].

Support Local Journalism.
Join the Orlando Weekly Press Club

Local journalism is information. Information is power. And we believe everyone deserves access to accurate independent coverage of their community and state. Our readers helped us continue this coverage in 2020, and we are so grateful for the support.

Help us keep this coverage going in 2021. Whether it's a one-time acknowledgement of this article or an ongoing membership pledge, your support goes to local-based reporting from our small but mighty team.

Join the Orlando Weekly Press Club for as little as $5 a month.