Introduction to the Beginning

The daily show.

That’s what was scribbled on the Comedy Central schedule grid, in the 11 p.m. slot, for months, as a placeholder, in 1995. What exactly would happen in that half hour of programming? No one really knew. Except that it would happen… daily.

Comedy Central itself was still a sketchy proposition at the time. In 1989, Time Warner, owner of HBO, had launched the Comedy Channel, the first cable channel devoted solely to comedy-based programming. Five months later Viacom, owner of MTV, had launched a competitor, Ha! The Comedy Channel featured a mix of quirky original shows and clips from standup comics; its signature creation was Mystery Science Theater 3000. Ha! countered with some low-budget original shows plus a wealth of reruns, including full episodes from Saturday Night Live’s middle years.

The Gulf War, beginning in August 1990, was a breakthrough for cable news, with CNN showing there was a large audience for round-the-clock coverage, even though the big three networks still dominated the nightly ratings. Further up the dial, Ha! and the Comedy Channel merged, reemerging as Comedy Central in April 1991. And in a bar in Manhattan, a comedian on a blind date had an insight that would eventually help connect those wildly disparate developments.

“I was at a sports bar, and all the TVs were turned to the war instead of sports,” Lizz Winstead says. “CNN had replaced their fancy reporters with young people, and they were on roofs, and there was green, and there was a theme song and all this shit. And I just thought, ‘Are they reporting on the war, or trying to sell me a war?’ Then the guy I was with said, ‘This is really cool,’ and I was like, ‘Oh my God, I might be on to something.’”

The blind date didn’t lead anywhere, but Winstead’s brainstorm eventually did. In 1995, Bill Maher announced that he and Politically Incorrect would be jumping from Comedy Central to ABC after the following year’s elections. To replace PI at 11 p.m., Doug Herzog, Comedy Central’s new president, wanted a topical show that would brand the network and appeal to young male viewers. The model he kept in mind was ESPN’s SportsCenter.

To develop the show, Herzog recruited Madeleine Smithberg, who had been a producer at Late Night with David Letterman. The thirty-six-year-old New Yorker had also been in charge of a quirky talk show that ran on MTV in 1993 before being syndicated by Paramount, which then used it, for one season, as a replacement for the canceled Arsenio Hall Show.

Smithberg hired, as the head writer for the new Comedy Central show, a comedian who lived upstairs in her Chelsea apartment building—Lizz Winstead. Smithberg had hired Winstead to work on the old MTV show, and the pair had been talking to Comedy Central about a new idea, a satire of a failing cable network. Herzog steered Smithberg toward the nameless late-night show instead. She and Winstead, a thirty-four-year-old Minnesota native, worked through ideas for nearly a year, settling on a news parody format. “Madeleine was the brains and the structure,” Winstead says. “She really knew how to run a show. And I was the person who knew a lot about politics and a lot about humor. I thought we should make the show itself a character. And we needed to differentiate ourselves from ‘Weekend Update.’ So we would operate like a newsroom, but be a comedy show.”

Herzog’s first choice to host the fledgling show was Craig Kilborn, who had built a following as a smart-ass talking head on SportsCenter. “He was sort of doing his bad version of Dennis Miller, who was a hot guy at the time,” Herzog says. “Craig met with me, and Lizz, and Madeleine, and Eileen Katz [Comedy Central’s head of programming at the time]. And I thought in the first five minutes that they were going to strangle him. The first thing Craig said was, ‘Some of you guys worked at MTV?’ And Eileen and I had come from there originally. ‘Yes, why?’

“Craig goes, ‘You know Downtown Julie Brown?’ We go, ‘Yeah, sure.’ He goes, ‘Because I love brown sugar.’

“That’s how the meeting started. Craig actually managed to bring it all the way around, and by the time the meeting was over they were like, ‘That’s our guy.’”

Writers were hired—J. R. Havlan, Tom Johnson, Ray James, Kent Jones, and Guy Nicolucci—as were the first batch of “correspondents”: A. Whitney Brown, Beth Littleford, and Brian Unger, plus Winstead. Lewis Black, a dyspeptic standup, came on as an Andy Rooney–type commentator who would deliver rants pegged to wacky news video clips. But as the program’s debut date closed in, no one could come up with a suitable name. Until one day Smithberg called Herzog: “Why don’t we just call it The Daily Show?”

It premiered on July 22, 1996, at 11:30 p.m. The format loosely tracked that of a conventional newscast: five or so opening minutes called “Headlines,” read by Kilborn from the anchor desk, followed by “Other News,” then usually a pretaped “field piece” with one of the correspondents, and finishing up with Kilborn interviewing an actor or a musician promoting their new movie or TV show or album.

Some segments played off the hard news of the day, like the presidential contest between Bob Dole and Bill Clinton. “There was more of a pop-culture-and-lifestyle component only because what we were satirizing—particularly local news—was doing a lot of that stuff,” Winstead says. “We would make fun of the conventions of news. Like when TV reporters talk, how do you create drama in a story that doesn’t exist? Brian Unger, who had been a producer at CBS News, invented what it means to be a Daily Show correspondent.”

Yet the tone of Kilborn’s Daily Show could be mean-spirited. A headline called “Operation Desert Shield Me from Impeachment” included a joke that investigators were having trouble analyzing the stain on Monica Lewinsky’s dress because it was mixed with “liver-flavored Alpo.” Field pieces often centered on true believers in UFOs and aliens.

The day-to-day creative process of the first few years of The Daily Show centered on Smithberg, Winstead, and the writing staff, which now included Paul Mecurio, Jim Earl, and Steve Rosenfield. “My first day on the job,” Winstead says, “I have to pull the writers into my office and say, ‘Guys, you can’t have your mushroom dealer come up to the office.’” Kilborn came up with the signature “Five Questions” conceit for guest interviews, but otherwise largely read from the script.

In November 1996, after Bill Maher’s exit, Comedy Central’s executives moved The Daily Show to 11 p.m. in part to counterprogram the late local news—and in part because they knew their low-budget operation had no real hope of competing with the late-night mainstream comedy powerhouses. The war between David Letterman and Jay Leno to succeed Johnny Carson at the helm of The Tonight Show had been national front-page news in 1992 and 1993, and Comedy Central was available in fewer than half of American households. Leno took over the flagship NBC show, but Letterman’s new Late Show on CBS was scoring high ratings, too. Each attracted around six million viewers per night. Kilborn’s Daily Show would peak at a nightly average of 357,000.

Yet Kilborn’s audience was growing and the show was generating critical buzz, helped by the addition of correspondents Mo Rocca and Stephen Colbert. Perhaps more important than the chatter was the fact that the Daily Show audience was indeed reaching the younger male viewers Herzog had targeted in the first place. The combination caught Letterman’s eye, and in 1998 CBS offered Kilborn its 12:30 a.m. Late Late Show slot.

“He starts to get a little heat, we’re starting to get a little attention with The Daily Show,” Herzog says, “and then the next thing you know Kilborn goes and signs with CBS without even telling us.”

Panic, followed by auditions: David Alan Grier, Michael McKean, Greg Proops, Bill Weir, and Mike Rowe came to the Daily Show studio and sat in the host’s chair. Littleford and Colbert got tryouts, too. But Herzog and other Comedy Central executives wondered about a guy who had hosted the short-lived MTV talk show produced by Smithberg, a black-leather-jacket-wearing standup comic. He had lost out to Conan O’Brien as Letterman’s NBC replacement; he had written a book of satirical essays; he had played Eve Harrington to Garry Shandling’s Margo Channing on The Larry Sanders Show; and lately he’d had some supporting roles in Hollywood romcoms. Herzog didn’t think the highly regarded, slightly adrift comedian would be interested in the Daily Show job. But hey, what did he have to lose in buying lunch for Jon Stewart?