Lisa Rogak - Angry Optimist

“Colbert is the total opposite of Jon,” he continued. “He’s very upbeat and personable. He’ll call out something and say, ‘Can you believe this is going on?’ while Jon is more like, ‘These assholes, look what they’re doing, let’s rake these guys over the coals and make it smart and funny because these guys are doing stupid stuff.’”

The two comics, of course, have their own takes on things.

“Jon deconstructs the news, he’s ironic and detached,” said Colbert, “while I falsely construct the news and I’m ironically attached, I’m not detached at all, I’m passionate about what I’m talking about. I illustrate the hypocrisy of a news item as a character . So while Jon’s just being Jon on the show, conversely, that’s me not being me, that’s me being that Stephen Colbert guy.”

When it comes to politics, comedians tend to be iconoclasts, and anti–status quo. “Jon is admirably balanced,” Colbert continued. “Every time I work with him on something, he tries to perceive the true intention of the person speaking, left or right, regardless of whether it was something he believed in or not. He wants to honestly mock.”

In the end, however, they’re both after the same thing: “Basically, it’s a bunch of guys exchanging ideas, laughing about stuff, and getting excited about smart funny ideas,” said Wiltfong.

It didn’t take Colbert long to break out of the pack of correspondents. He filled in for Jon as guest host on The Daily Show for the first time on January 24, 2001.

Although Jon and Stephen spent a lot of time working and laughing at the studio, their friendship was mostly limited to the office. “In theory, I think Jon would be excellent company,” said Colbert. “But I have nothing to back it up.”

“The biggest mistake that people make is thinking that Jon and Stephen sit down before every show and say, okay, how are we going to change the world, or some bullshit like that,” said Karlin. “They both really just want to get a laugh.”

Even though he preceded Stewart on the show, Colbert admires and looks up to the host. “Jon’s very generous and treats me like a peer,” he said. “I think I still think of him as an older brother, he comes before I do, he has bigger numbers, it’s hard to do a strip show, he’s taught me a lot, how not to worry about what goes on outside the building and just get our work done every day.”

As the mutual love fest continued over the years, some at the Show noticed that they began to shut others out. “One negative aspect of working with Colbert from the perspective of the other correspondents was that he was very tight with Jon,” said Wiltfong. “Jon and Stephen were always very friendly and chummy with each other; on set or during rehearsals they were the best of friends, but it was an unusual occurrence when other correspondents engaged Jon in conversation.”

On election night in 2004, all the correspondents were in the studio for the live broadcast. During the rehearsal, the correspondents sat in a corner while Stephen and Jon sat at the desk bullshitting with each other, making no attempt at conversation with the others. “It always seemed like a world we couldn’t get into, and it always struck me as curious,” said Wiltfong. “I didn’t know why that dynamic existed and I wasn’t the only one. Ed Helms and I are relatively friendly and we talked about that, but Jon just doesn’t let many people in and Stephen was one of the few.”

Part of the problem, unvoiced among some, was that the close relationship between Stewart and Colbert—along with an increase in Colbert’s guest host appearances—meant that it was clear who was going to be next in line, who was already succeeding more than the rest. “There was grumbling among fellow comedians that you don’t want to see another comedian succeed because it means less laughter and stage time for you,” said Wiltfong. “That’s part of the business.”

In addition to clearly favoring Colbert over the other correspondents, it was an open secret that women staffers were in short supply on The Daily Show, at least in the writers’ room, which was, after all, where much of the spin and overall tone of the show was set.

When Olivia Munn first went on the air as a Daily Show correspondent in 2010, she was the first new female correspondent to be hired—or at least the first to make it past the freelance correspondent stage—since 2001 when Samantha Bee had joined, and who was still filing regular reports in 2014. Despite her longevity, Bee admitted that she found the atmosphere uncomfortable at times.

“She struggled with being the only woman on the show in what is a male-dominated industry to begin with,” said Wiltfong, who shared an office with Bee when he was on the show. “She felt like the low person on the totem pole, and that’s not a good thing to feel as a performer.”

Lauren Weedman also worked on the show as an on-air correspondent from 2001 to 2002. (Though correspondents are “hired,” they’re only paid for each report that airs.) “I was told when I was hired that they have a very hard time finding and keeping women, and that I was lucky to get a one-year contract,” she said.

She added that hearing her coworkers’ comments didn’t help. “Everyone kept saying, ‘It’s sooo hard to keep women here,’” she said.

Some felt that Weedman had a distinct disadvantage going in: her comic schtick was essentially that of a very annoying woman. “My comedy came from being kind of insecure, broken, needy, neurotic,” she explained. “And that works in a group of guys if you’re a nerdy, insecure guy and you can all just banter away. But if you’re a woman, it’s harder to be that person without some support.”

Whether it was from nerves from being on national TV, being a little bit starstruck, or just her personality, Weedman’s routine spilled over into the office atmosphere, where it was clear that given the stress of producing a tightly planned show on an even tighter schedule, Stewart had no time or inclination to deal with what he viewed as a problem employee. Whether Stewart had a deaf ear toward certain kinds of comedy or whether he just didn’t like having a female correspondent with Weedman’s style around the office was unclear, but Stewart’s makeup person told Weedman that he had definite issues with her, suggesting that he thought she was making fun of him. “‘He can’t tell that you’re kidding,’” she said. “‘I’ve known him a long time and I just think he doesn’t get your kidding. I would go right now and talk to him. Like how you talk to me. Like how you talk to everyone but him.’”

Weedman spoke with Stewart, who apparently alleviated her concern, but the constant stream of women coming into the studio each day on auditions told her otherwise. “They were always having auditions for women,” she said. “I would see all these blond women coming in—they’d give them the same copy they gave me the night before. And I knew I’d be fired.”

Soon enough, she was fired, though according to what one colleague told her, her termination had nothing to do with her talent or her approach to comedy.

“One of the issues that got in the way of my success on the show was that I just wasn’t as cute as the other female reporters,” said Weedman. That colleague apparently told her, “I’m not saying that I don’t think you’re cute. I’m just talking about guys, the fans of the show, the American people, and all the Comedy Central executives.”

“Did I feel like there was a boys’ club there?” Stacey Grenrock-Woods, a former correspondent on the show from 1999 through 2003, asked rhetorically. “Yeah, sure. Did I want to be part of it? Not necessarily. So it kind of goes both ways.”