Inside the Chaotic Early Days of ‘The Daily Show’

Comedy Central was in a tight spot. With Bill Maher’s Politically Incorrect moving to ABC, the fledgling network was in desperate need of a talk-show replacement. And so, on July 22, 1996, The Daily Show was born.

Co-created by Lizz Winstead and Madeleine Smithberg, who had worked together on the short-lived The Jon Stewart Show, it was a novel concept: a parody of newscasts delivered with deadpan panache by ex-ESPN anchor Craig Kilborn and a roving team of kooky field correspondents, including Stephen Colbert and Lewis Black. It began as a blend of politics and pop culture but tensions between Winstead and Smithberg and Kilborn came to a head two years in, culminating with a deeply sexist Esquire interview wherein Kilborn called the staff “bitches” and said of Winstead, “If I wanted her to blow me, she would.”

That was the final straw for Winstead, who walked away from the show in 1998. The following year, Jon Stewart took over as host of The Daily Show, and the rest is history.

“If it had never gotten on the path, it would have been difficult to walk away. But it was on the path. It was going. It was all happening,” explains Winstead.

Winstead would go on to co-found Air America Radio, which helped launch the careers of Rachel Maddow and Marc Maron, as well as Abortion Access Front, an organization fighting for women’s reproductive rights. On July 19, Winstead, Smithberg, and a number of original Daily Show correspondents will reunite for a talk in honor of the show’s 25th anniversary, with proceeds benefitting AAF.

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“We’ve never all been together and told these stories publicly before, so it’s going to be a lot of fun,” offers Winstead.

But first, she spoke with The Daily Beast about the early days of The Daily Show and how she and her team laid the groundwork for 25 years of groundbreaking comedy.

It’s crazy that it’s been 25 years of The Daily Show. What goes through your mind when you hear that?

It feels surreal in the sense of how, 25 years ago, we created a show because our media wasn’t doing its job, and through all the iterations of how the media wasn’t doing its job, we’ve landed now in 2021 where the media finally started doing its job and right-wing conspiracy theorists have decided that the media isn’t doing its job because it’s doing its job. It’s really wild. But the thing that’s the coolest for me is, the one thing you have in this world—you as a journalist, me as a comic, writer, and producer—is if your instincts are right, it keeps you going forever. And just to know that all the instincts I had about that show—the framework, who to hire, what subjects to tackle—paid off in spades to the point where you could bring in new hosts, and new casts, and new writers and have a foundation so solid that they could reimagine it while the basic structure held up.

You’d worked on The Jon Stewart Show just prior to co-creating The Daily Show, and I remember when that show ended, David Letterman came on as one of the final guests and basically said, “This is only the beginning for you, Jon.”

And then Letterman signed up Jon for a development deal for two years, and we launched The Daily Show with Craig Kilborn. I think Letterman saw Jon as a threat because of his talent, and thought, “What if I locked this guy up with a deal and kept him off the market for a while?” I remember how Letterman came on the show and was enamored with how young the audience was, and how youthful the staff was. He really seemed to like the vibe and I think he really liked Jon a lot.

Well, we know he was generally enamored of “youthful” staff. With The Daily Show, Comedy Central was looking for a replacement for Bill Maher’s Politically Incorrect, right?

Yeah. They wanted a replacement for Politically Incorrect, and they wanted a show that was responding to the world. What was interesting—and lucky for us, and crazy—was that they recognized that, in developing a show that was going to be on five nights a week, just doing a pilot wasn’t going to work, so they gave us a year without a pilot in order to allow us to grow on the air. What Madeleine and I knew for sure was that the media and the news had to be a character on the show, and we had to do everything in our power to not be some extended version of Weekend Update. So, in order to hold a mirror up to the media, we hired people from the media who were writing at magazines, producing at TV news, and working as correspondents on TV news. We realized that we had to bring the news and be funny, so we formatted the show each day as you would in a newsroom. And people forget, this is before YouTube and Google, so I think we stole a LexisNexis account from somebody, had the AP wire, and would get dozens and dozens of newspapers delivered to the office every day, with producers divided into regions. It was really ragtag and really fun. We only had six writers at the beginning. It was insane.

And Comedy Central were the ones who chose Craig Kilborn to be the host, right?

Yup. [Viacom President] Doug Herzog loved SportsCenter and wanted this kind of SportsCenter vibe, so Kilborn filled the role. When the show launched, the show was more like Colbert’s original show [The Colbert Report], in that there wasn’t anyone who was really the voice of the people—everybody was in character—and Craig looked and sounded like every local news anchor, and was a person where everybody wondered, “Are you in on the joke? Or are you not in on the joke?” And we never wanted to give that part away, because that was part of the magic of the show.

I had read how in the early days there was this tension between Comedy Central and Craig, who wanted it to be more pop culture-focused, and yourself and Madeleine, who wanted it to be more of a riff on media, politics, and the news.

Yes. It’s no secret that the core creative team fought very hard against prioritizing pop culture. A) They wanted to have celebrity guests on, and we thought, “Why are we shitting on Hollywood if you want to have these people on our show?”, and B) An entertainment satire of Entertainment Tonight is called Entertainment Tonight. I can’t make that show any more hilarious than it already is. We certainly did not make lasting friendships by fighting tooth and nail against this, but I would argue that if Madeleine and I had not fought as hard as we did to keep politics front and center, I don’t think we’d be having a conversation about the 25th anniversary of The Daily Show. I don’t think we would have created a show that Jon would have wanted to step into. People weren’t getting information from the news, and to be able to point that out was a real catharsis for people.

As you said, you, Madeleine, and your staff were responsible for laying the foundation. And a big way you did that was through hiring people like Stephen Colbert, Lewis Black, and a number of other folks.

Stephen Colbert was on Good Morning America doing these interviews, and I was watching one morning and went to Madeleine, “Stephen Colbert is on Good Morning America and he is winking to us, and I think we should talk to him and see if he wants to come over here.” So, we got him over here. Stephen Colbert, Lewis Black—and Brian Unger is the reason you know what a Daily Show correspondent is. He came from CBS News and literally trained every correspondent on how to do that ridiculous, skeptical, know-it-all, Stone Phillips-y kind of thing. Right when I was leaving Carell came on, and Madeleine shepherded through him and a bunch of other people.

What was Colbert like when he arrived? Had he developed that Colbert persona yet?

When I saw him on Good Morning America, it already seemed like he knew how to be a journalist, and he’s also a really funny comedic actor, so I don’t think he needed a whole bunch of coaching. I just think that every single person came in thinking about how they were gonna be, and as the news stars of cable emerged—Fox News came into the realm in October of 1996, and we launched in July—paying attention to these personas that were being built and what he wanted to take on, I think Stephen observed a myriad combination of the O’Reillys, the Hannitys, and that self-important, bombastic thing, and he ran with it.

I wanted to talk to you about the falling-out with Craig.

Oh, I don’t ever talk about that. You can google it and write about it.

I re-read the things that he has said at the time and it was pretty shocking.

Yeah. It wasn’t great. But I worked in television at a time when shit happens, and I think things would have been very different if it had happened now.

Did you tell Comedy Central, “Him or me?” And how difficult was it to walk away from your creation?

You know, I think anybody who’s got any confidence and who says, “I made this thing, I can make a lot of other things…” Truth be told, it was in me to say, “There can’t just be one of these shows. I could stay here forever and do this show, or I could go out there and try to do other things so that the media landscape starts to get populated with cool stuff.” So, I left there, and then Brian Unger and I did a pilot that I wish would’ve gotten picked up, which was a satire of a news magazine, and then went off to launch Air America. When I look at Rachel Maddow, and Marc Maron, and Sam Seder, they all leapt out of that. I got to write a book, and now I’m running a reproductive rights organization that’s talking about abortion in a way that’s really provocative, and edgy, and funny. I just feel like I’ve been following my path, and all the while doing stand-up as it was happening.

Did you have a hand in Jon Stewart ultimately getting the gig, given your past with him on The Jon Stewart Show?

Everybody would have loved for Jon to not be in a development deal with Letterman, because we loved working with him. So, it was just a perfect storm where when Craig was leaving, Jon’s development deal with Letterman was coming to a head, so people thought, “Let’s see if he wants to come in and do this.” And when he did, it was such a good transition because I think the show just grew. Having somebody in the chair who was the voice of the viewer allowed him to bring the antics in the field back to the reality of what they were satirizing, and when you have somebody as profound in their own persona to be able to fill that chair, it was an incredible direction and ended up bringing the show to the next level. He asked me to come back, and at that point I was like, “You know what? You’re filling the role that I was doing and you’re also in the chair, so good. You just do that. What would I do? It would just be like having two brains there.” I feel so lucky that, in the iterations of this show, people made really good decisions about who was going to be in that chair.

Lastly, let’s talk about Abortion Access Front—your organization that the Monday Daily Show reunion is benefiting.

It’s a relentless fight. For the amount of bad stuff that’s happening, the lack of media coverage around it is staggering. The fact that Roe v. Wade is probably going to be overturned in 2022—and that’s not hyperbole, that is facts—and there’s been hardly any cable news coverage around it, I was like, you know what? I want to hold these people accountable and bring information to the people. We go out on the road and do shows with comedians and musicians, have conversations with local abortion providers and activists on the ground, make hilarious videos that are really poignant—our TikTok is blowing up—and we’re launching our own YouTube talk show in October called Feminist Buzzkills Live—basically, if there was a talk show that discussed real issues in a real way around patriarchy, and women, and abortion, with really great comics and musicians, as well as experts and providers in the field. It’s not talked about enough, and is so stigmatized, that we’re just going to blow the roof off the motherfucking abortion building.