History doesn’t just favor the winners. In some instances, it can seemingly turn everyone who isn’t a winner into a loser by default. For two and a half years, The Daily Show existed without Jon Stewart at the center of it, but as Stewart prepares to pass the torch to Trevor Noah, you’d be forgiven if you weren’t aware of Craig Kilborn’s version of the show. After all, it’s been 16 years since Kilby dance, dance, danced his way off the Daily Show stage on the way to The Late Late Show and greener network pastures, and that’ s a lifetime in the digital age. Especially when all anyone (understandably) wants to talk about is Jon Stewart’s legacy as the most trusted name in news.
At its inception, though, The Daily Show was supposed to mock, poke, and even impersonate the newsreaders, not outdo them in matters of trust and purpose.
“We were going to make fun of them by becoming them. We would operate as a news organization while acting like a comedy show,” wrote Daily Show co-creator Lizz Winstead in her book, “Lizz Free or Die Hard” according to CityPages.
As an inspiration for the kind of oblivious mannequin that the developing Daily Show was in search of, one mid-’90s news staple seemed to be the perfect model: Dateline anchor Stone Phillips. So vital to the development of the Daily Show‘s initial tone was Phillips that Winstead’s producing partner and former neighbor, Madeline Smithberg joked to Dame Magazine that he almost deserved his own co-creator credit.
“We studied that guy. It became, Okay, we pretend we’re him and mix it with stories that are much more absurd.”
Of course, finding a fake anchor is a lot harder than it may seem. Winstead and Smithberg sifted through comedians (too jokey and too eager to comment on the material) and local newsmen and features reporters (too wacky) during the nearly one-year run-up from pitch to air. They even thought about bringing in Jon Stewart, who they had both worked with on The Jon Stewart Show, but he was unavailable at the time. Craig Kilborn, on the other hand, was interested and able to be snatched up, and he had the eye of Comedy Central executive Doug Herzog, making the former Sportscenter anchor a slam dunk to lead the team.
It’s important to remember not just that The Daily Show existed before Stewart, but that it was successful. Stacked with on-air talent (Kilborn, Brian Unger, Beth Littleford, A. Whitney Brown, Lewis Black, and Stephen Colbert) and powered by Winstead’s work as the head writer, the late ’90s version of The Daily Show stood out as a smart and hip parody of the nightly news and magazine shows, but one which only threw jabs at its targets and sometimes punched down to get its laughs.
Frothy is an apt description of the 1996-1998 Daily Show, and Kilborn, a blonde giant with a winning smile and a propensity for smugness, came off as a likeable bully and the perfect host for that kind of show. But things were not perfect behind the scenes and Kilborn’s on-screen persona started to lose some of its appeal when, in the fall of 1998, he told Esquire, “There are a lot of b*tches on the staff, and, hey, they’re emotional people. You can print that! You know how women are — they overreact.” adding, “To be honest, Lizz [Winstead] does find me very attractive. If I wanted her to blow me, she would.”
Consider, for a moment, the kind of justifiable outrage and the loud response that such a remark and rumors about a hostile work environment would get now. Then realize that Kilborn got a one-week suspension without pay and Winstead, the show’s co-creator, head writer, and an on-air correspondent, left shortly thereafter, unwilling to work with Kilborn, according to comments made to the Minnesota Star Tribune.
“I didn’t know how I could do my job to the fullest feeling the animosity that I felt reading the Esquire article,” she said. “I worked for two years, 15 hours a day, trying to make him a star and that show a success. It was really hurtful, and it was like, ‘Why did you have to say that?'”
Winstead also spoke out about her larger issues with Kilborn in that same interview.
“I spent eight months developing and staffing a show and seeking a tone with producers and writers. Somebody else put him in place. There were bound to be problems. I viewed the show as content-driven; he viewed it as host-driven.”
Though a mass staff exodus did not occur, it’s clear that there were people who did not agree with Comedy Central’s seeming choice of Kilborn over Winstead. “She was gone and he was still there and it was her show and I thought that was f*cking appalling.” said Lewis Black to The Daily Beast in 2013, later calling Kilborn “a prick” when asked about him in an interview.
Also appalling? Kilborn’s seeming lack of self-awareness over the remark that had caused so much trouble, as evidenced by the Aug. 20, 1998 episode wherein he joked about carrying on a relationship with an intern in the midst of a bit making fun of concerns that a string of cruise missile strikes might lead to a war. And if you need a clearer contrast between Craig Kilborn’s comedic sensibilities and Jon Stewart’s, I don’t know that I can help you, though Kilborn’s needless swipe at the legendary George Carlin in the same episode might also do in a pinch.
By that point, however, Kilborn’s exit was already in process. Much to the apparent dismay of executives, who tried to get their lawyers involved in an effort to keep him from getting out of his contract early to go to CBS and host The Late Late Show.
Was it a big loss? In the here and now, it’s easy to say no. Kilborn’s Late Late Show term was middling and he was creatively overshadowed by his successor (Craig Ferguson) there as well. As for what he’s been doing over the last decade, well, not much.
In August of 1998 when it was announced that Jon Stewart would succeed Kilborn, though, he was no lock for success. Especially after failing in his other attempt at a late night show and being passed over by both Lorne Michaels in pursuit of David Letterman’s old Late Night slot and CBS (and producer David Letterman) when they chose Kilborn to replace Tom Snyder, who Stewart had spelled on occasion. But despite any outside notion that Stewart might be damaged goods, Comedy Central got their man the second time around thanks to a conversation Stewart had with Smithberg about a personal offer from David Letterman to produce The Late Late Show (she declined) and his familiarity with Comedy Central executives like Eileen Katz and Herzog, who had also worked with him at MTV. Unfortunately, while Stewart’s arrival seemed like a big happy reunion, one key player alluded him — Stewart tried to bring Winstead back, but she declined.
Absent Winstead’s voice and the need to service Kilborn’s smarmy character, The Daily Show moved forward with Smithberg and a new host/executive producer who got more and more involved in the editorial direction of the show, albeit slowly, according to longtime writer J.R. Havlan, who told THR:
“I’ve always been amazed at how well Jon handled the transition. He didn’t rock the boat. Instead, he used that first year to gradually make the adjustments necessary to create the foundation for what the show would eventually become. I’ve always marveled at his patience, focus and foresight during that time.”
Would that have happened had Winstead said yes to a return or would her strong vision and Stewart’s strong vision have clashed as the show became both host (and correspondent) driven as well as content driven while pulling away from some of the on-camera meanness that had been a part of her era?
“In the olden days,” said Stephen Colbert to The AV Club in 2003, “you wanted to take your soul off, put it on a wire hanger, and leave it in the closet before you got on the plane to do one of these pieces.” We had deep, soul-searching discussions on flights out to do stories, going, “We don’t want to club any baby seals. I don’t want to hold this person down and kick him in the teeth comedically.” But he did because, as he put it, “you had to come back with something funny.”
Former correspondent Ed Helms put it more succinctly in the same interview when he said, “When I was a fan of the show watching it, there was a lot of mean-spirited stuff, and how f*ckin’ easy is that? It’s so easy to show up and chew somebody a new asshole.”
Changing the culture of The Daily Show, however, would not be easy and, as unfair as it is to say this, would have likely been harder with another cook in the kitchen and another remnant of the past status quo, even if Winstead had been in lock-step with Stewart, who struggled initially to get along with his inherited staff and who, despite early raves, didn’t stand out as a clear upgrade to Kilborn to everyone initially.
“The crystal-clear joke that we were a parody of the news,” had left with Kilborn according to Smithberg, who told The New York Times that, “you really believed that Craig was that guy behind the desk […] He looked like everyone you’ve ever seen on TV. Jon Stewart has an unbelievable range of things that he’s capable of doing, but he delivers headlines like a guy telling jokes. He’s brilliant, but you don’t really believe he’s a news anchor.”
A fair assessment then, but something that Smithberg (who left the show in 2002 to spend more time with her family) might take back now if given the chance. After all, we’ve all watched as Stewart transformed the show from a hollow parody into a biting satire. And we’ve seen him morph from a comedian to something more during the 2000 Election, the 9/11 aftermath, and later The Bush Presidency, the financial crisis, The Obama Presidency, and a thousand fist pounding, heart kicking, teeth clenching, howl into the night moments that were made a tiny bit easier to live through thanks to The Daily Show, the most important television program, ever… sorta.
