Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

“I feel like I’m that much harder to get rid of because the guy who runs the show loves Ally,” Greenberg jokes.

  At least once, the office dogs have made it onto the air. In January 2009, Anderson Cooper conducted a dog debate—tagged as a Puppedential debate in a series called “Road to the Doghouse”—to help the Obamas pick the best dog to live in the White House.

  The dogs in the office have had a kind of chain reaction effect. Formerly dog-free employees who end up spending a lot of the workday around dogs will often go out and adopt one of their own. Former correspondent John Oliver is one of them. He adopted a golden retriever puppy named Hoagie in late 2011 because “she really doesn’t give a shit about The Daily Show, which I find enormously helpful at the end of the day.”

  He brought her to the studio one day when she was still a puppy, but she became so excited by the other dogs that she just wanted to play, and that created problems for Oliver when he was under deadline.

  With that said, he is grateful for the canine company. “I don’t know what we would do without these dogs,” he said. That difference was made clear one day when Pervez Musharraf, the former president of Pakistan, was a guest on the show and a memo went out the day before that all staff dogs had to stay home because of the bomb-sniffing dogs that would be checking the place out before Musharraf’s arrival.

  “We could really feel the difference when they weren’t here,” said Oliver. “It would be a very different place if there weren’t dogs walking around.”

  Though Daily Show staffers first started to bring their dogs to work during the Craig Kilborn era, Stewart has done his part to actively encourage it, with a few limits. “It makes for a very nice environment,” he said. “There are rules and everybody has to be responsible. You gotta potty train them. You gotta make sure that if there are issues with other dogs that they are dealt with the right way.”

  The combination of dogs roaming through the halls and the free food available created an uncomfortable situation for a period of time. “We went through a period where we had to tell people to stop feeding the dogs off the catering table, because six months into it, everybody looked like Dom DeLuise!” said Stewart. “The dogs were just lying on the floor, bloated, and ready to pass out. So we’ve instituted some discipline, but it’s really nice to have them around.”

  In addition to helping the employees feel better, the dogs also make guests, some of which have included Jennifer Aniston, Ricky Gervais, and Betty White, feel more at ease before they head out in front of the camera for a segment with Jon. When Senator Barack Obama made his first appearance on the show, he immediately sprawled on the floor to commune with the dogs.

  * * *

  “As a comedian, there’s a lot of love you get from an audience’s laughter and applause,” said Bob Wiltfong, who worked as a Daily Show correspondent from 2004 to 2005. “As a professional comedian, it’s my theory that people get into comedy because there’s something missing in their own personal life, and they need that void filled through laughter and acceptance onstage.”

  “Some of the most miserable people I’ve ever met are comedy people,” he noted, though he added that Colbert was one of the rare exceptions. “It made for an interesting dynamic at The Daily Show, which had some of the smartest, funniest people I’ve known, all moving toward one common goal, but the flip side was that there were a lot of miserable curmudgeonly people working there. In general, comedy just isn’t an environment that lends itself toward happiness.”

  “It’s like a dysfunctional family,” said Lewis Black.

  Even though it’s their job to be funny, the pressure of meeting a regular nightly deadline as well as constantly trying to figure out where you are in the pecking order takes its toll on people putting together a comedy show, whether they’re writers or on-air talent. Wiltfong also noticed the different ways in which Jon and Stephen approached their jobs. “What you see on air with both those guys is pretty much what they’re like off air,” he said. “In order for Jon to do some of the comedy on The Daily Show for so many years and for it to be high quality, it has to come from a place of anger, because then it’s truly biting and gets at the truth. In real life he’s not a ball of laughs, because he’s pretty upset about what’s going on in the world.”

  “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.”

  Hallie Haglund, who started working as a Daily Show writer in 2009 after working in several other positions on the show since 2006, offered another perspective. “I do think there is a huge element of shared experience,” she said. “So much of our show is comic book shit that I have no idea what people are talking about, or something from Star Wars I’ve never seen. And I can come in and help out on Sex and the City guest questions like I did yesterday.”

  Maybe the only women who could succeed in writing late-night comedy have a thick skin or grew up in a house full of brothers … or both.

  Writer Jonathan Bines helped launch Jimmy Kimmel Live in 2003, and even he admitted that “late-night writers’ rooms are not fabulous places to be. They’re miserable for everyone.” But that doesn’t mean female comedians don’t want to be there, and those who make it in the door know what they’re getting into.

  “That’s what’s fun, that’s why we get into comedy: to mess around with comedians all day,” said Ali Waller.

  “If you’re not comfortable with sexual humor or with crudeness or with … people being really honest about certain emotions, then … this job is not for you,” said Daley Haggar, a female comedy writer whose résumé includes The Big Bang Theory and South Park.

  “It’s a very aggressive medium, and it’s not the medium for fragile flowers,” said Janis Hirsch, a veteran comedy writer whose résumé includes Frasier, Modern Family, and Will & Grace. “It’s a job, it’s not a perfect world. Women have to either nut up and get into the spirit of it or not look for a job on a show that’s all about men.”

  To be sure, female writers have never been found in great quantities on most late-night talk shows. And 80 percent of late-night hosts are male, Chelsea Handler being the exception. “When you’re writing for late night, you’re writing through one person’s prism, and that person at the shows you’re looking at is always a dude,” said Hallie Haglund.

  “It’s the law of averages,” said Lizz Winstead. “More guys than women are in comedy.” In fact, when she and Smithberg started The Daily Show in the pre–Jon Stewart days and solicited writers to work on the show, they received over a hundred résumés, but “only about three or four were from women.”

  So while former female employees and correspondents—as well as members of the general public—may often complain about the boys’ club at the show, the truth is that the atmosphere behind the scenes at The Daily Show is not that different from other talk shows of its ilk. And given the cutthroat competition to snag a job at one of these highly popular programs, there will always be another person—male or female—willing to put their concerns aside in order to become part of a successful and visible franchise.

  * * *

  In addition to women on the show feeling slighted, some critics of the show believed that the overall tone of The Daily Show sometimes crossed an unnecessary line in the name of comedy, verging on the edge of nastiness just to get a laugh. Stewart disagreed wholeheartedly.

  “We rarely do ad hominem attacks,” said Stewart. “In general, it’s based in frustration over reality.”

  “We claim no respectability,” added Colbert. “There’s no status I would not surrender for a joke, so we don’t have to defend anything.”

  At the same time, even though the overall tone of The Daily Show is satirical, “The show is our own personal beliefs,” said Stewart. “That’s the only reason why we go to work every day. You try not to let it become didactic, you always remember it’s a comedy show more than a political satire, but we very much infuse it with who we are.”

  Though he had no straightforward news reporting experience, Stewart thought he approached his work in the same spirit, if not sometimes better than the professionals. “I think what we do is relatively well thought out,” he said. “And while there are times we step over a line when things are happening fast and furious, the truth is, as fake journalists, we exercise far more restraint than the journalists I see.” He cited how the media handled the aftermath of the Columbine shootings, where TV crews essentially mobbed students and their families. “I had never seen anything like that,” he noted. “We didn’t make one joke about it, so as far as our comedy being in the depths, I think we’ve got a long way to go toward the bottom until we take on the actual ethics of real journalism.” />
  “He doesn’t want to rip the curtain back and let people see that there is medicine being delivered here,” said Devin Gordon, formerly a senior writer at Newsweek. “He also doesn’t want to sound too pompous and say, ‘Hey, I’m just telling jokes.’ They just happen to be about the headlines, but anybody who watches the show knows that there is a core of anger that is driving the entire enterprise.”

  And sometimes that anger is unleashed on the staff. Comedian David Feldman worked as a writer on The Daily Show and his memories of Stewart are anything but warm and fuzzy. “In my opinion, Stewart is very manipulative,” he said. “He’s a crowd pleaser and [only] gives the illusion of taking chances. I’m a staunch member of the Writer’s Guild of America and Jon Stewart fought his writers when they wanted to go union [in late 2006]. They went union and [he] has been punishing them ever since. If you watch the show, he doesn’t really do well-crafted jokes. He’ll throw a couple in, but it’s mostly mugging and shouting. He’s funny, but he’s punishing his writers. He doesn’t use his writers’ stuff because he’s mad at them for going union.”

  “My boss is like if you took Willy Wonka and mixed him with Hitler,” added correspondent Ed Helms in one Daily Show segment, but he delivered the line in a way that it looked like at least part of him wasn’t joking. “He’s crazy like Willy Wonka and he’s psycho like Hitler. But he doesn’t have a mustache.”

  Writers are not the only ones with stories to tell. A staffer recalls the time when Stewart’s temper got the better of him and he hurled a newspaper at Smithberg during a story meeting while screaming inches away from her face. He later excused his behavior by saying, “Sorry, that was the bad Jon … I try not to let him out.”

  “When I tell people that I used to work for Jon … they ask…, ‘Oh, is he nice?’” said former Daily Show correspondent Stacey Grenrock-Woods. “Now, I would never think of Jon Stewart as ‘nice.’ He’s a comedian, and comedians aren’t always particularly nice people. But these people look so hopeful.… So I always say, ‘Yes, he’s very nice.’ And they always say, ‘Oh, thank God. I don’t know what I’d do if he wasn’t.’”