Angry Optimist: The Life and Times of Jon Stewart

CHAPTER 8

“OUR ENTIRE DAY is focused on taking the un-fun we have and turning it into fun when it gets on the air,” said Stewart. “Because we function, actually, very similarly probably to a news show in that we have sort of an editorial meeting in the morning. It’s a really structured day. We actually do have a very good time doing it, but it’s sort of relentless, and the structure of our day is a lot more rigid, I think, than people would imagine.”

Looking at a day in the life at The Daily Show reveals that putting together each program is a never-ending process. The first bit of work starts around 7 A.M. when a team of producers settles in and starts to review TiVo’ed videos and news stories from the day before for potential images, sound bites, and stories that would make good fodder for that evening’s show. They also thumb through all three of the local New York papers—the Post is “our paper of record” according to one writer—for ideas and obscure and entertaining news stories as well. In addition, several television sets broadcast live feeds from all of the morning news shows from ABC, NBC, CBS, and cable networks like CNN and Fox News.

The writers start to wander in shortly before 9 A.M. when they gather in the writers’ lounge for a meeting that is known around the studio as “our morning cup of sadness.” That first hour is basically spent cracking jokes about the major news stories from the previous day while munching on bagels from H&H, a long-established New York bakery. It’s during that crucial hour when the first nuggets start to emerge. “We get specific about what angles we’ll be taking and we’ve all agreed to,” said writer J. R. Havlan. “We’re joking around from nine to ten, and those jokes frequently end up on the show.”

The team then breaks up to start writing that night’s show. Here, the joking out loud basically ceases as the writers focus on the task at hand. They are able to crank out a first draft of that night’s show in about ninety minutes. “We know exactly what we need to get done at any period of time,” said writer Jason Ross. “We’ve seen the videos and we know there are four good sound bites for the story. It’s pretty laid out for you.”

Producer Rory Albanese, for one, marvels at the writers’ speed. “They’re really fast and real good about it,” he said, adding that, as is the case with anything, practice enhances both skill and speed. “You get better at it. It’s a muscle and you work it out. It gets stronger.”

“You get good at knowing what you need to attack,” Havlan added.

Around 11:30, producers and research staff start to gather the scripts from the writers so they can begin to do their work, from selecting news clips to run alongside Stewart’s comments to locating props—occasionally making them from scratch—to accompany a monologue or sketch.

The next three hours pass in a blur as Stewart and the production team edit and tighten the scripts, further refine the jokes, and offer up suggestions to the research staff. Along the way, the tech staff plans their camera angles and video shifts, altering them with each new script draft that comes in.

The Daily Show writers and producers also have to be careful not to duplicate anything going on at The Colbert Report, which spun off from The Daily Show in 2005. Despite the distinct tone of the two shows, there is bound to be at least some crossover. “The game they’re playing is a slightly different one from us, so we don’t trip on each other that much,” said Stewart. “And let’s put it this way: This ain’t the Serengeti. There’s plenty of food to go around.”

When Ben Karlin was executive producer of both shows, he visited the two studios several times a day to check for any duplication. For example, when the Mark Foley sex scandal first broke in the fall of 2006, in which the Republican congressman from Florida sent explicit notes to a sixteen-year-old male page, Karlin green-lighted stories for both shows.

The Daily Show take: “It’s the Jewish Day of Atonement,” said Stewart. “I don’t know how many days of fasting can get you out of trying to bang sixteen-year-olds. My guess is at least three days. Even after that, probably a month of salads.”

Colbert, on the other hand, said that the media had gotten it all wrong about Foley, explaining that “stud” really stands for “Strong Teenager Using Democracy” in text-message shorthand, and that “horny” is short for “Happy On Reaching New Year’s.”

“Every January first,” he said, “that is the message I send to my buddies at Stephen Colbert’s Youth Camp for Young Studs: ‘I am incredibly horny.’”

Because Stewart serves as executive producer for The Colbert Report, he also reviews scripts for both shows before nailing them into the schedule. “He looks at our scripts, and helps us to see where to find the most fruit,” said Colbert. “His instincts are maddeningly good, and I don’t recommend going to the mat with him over a comedic idea. We actually talk way more now than we did when we worked together, because I now understand how difficult his job is, to executive produce and then to be the ultimate writing voice of everything that gets said. I need someone’s advice, so I call fairly frequently.”

While this frenzy is going on, part of the staff is out in the field working with correspondents to tape their segments, or working on projects that take longer to produce. According to executive producer D. J. Javerbaum, despite the luxury of time that these projects have, very often they’re just not as funny as the pieces done on the fly in a matter of hours. “Pieces thrown together in twenty-four to forty-eight hours often come out better than the ones you plan more,” he said.

Writers, researchers, and producers will pop in and out of Stewart’s office right up until rehearsal begins at four o’clock. First there’s a rough rehearsal where the writers, producers, and Stewart are listening and still tinkering with each word, image, prop, and nuance. Then they run through it again.

“In the studio, you do one rough run-through, where you’re bad and you flub your words and then squeegee the sweat off your eyebrows and do it again,” said Lauren Weedman, who worked as a correspondent from 2001 to 2002. “The first one is a stumble-through, and it is petrifying.”

“There are definitely moments in rehearsal where we go, ‘Wow, that’s a little strident, we might want to dial that down a bit,’” Stewart admitted.

“Very often it feels like you’re doing the five or eleven o’clock news because things are changing so rapidly and Jon wants to go as close to six o’clock as possible,” said director Rob Feld. “Once he puts that suit on at a quarter to four, he’s in show mode, and everybody feeds off that. It’s not live but you don’t want to screw up because he’s sitting in the chair and you don’t want to have to do the joke twice [during taping] since the audience has already seen it. You want to do your best for him because he’s bringing his triple-A game every time.”

After the rehearsal ends, a feverish flurry of rewrites ensue, and then, no matter what kind of shape the script and performers are in, the audience begins to file into the studio around 5:30; some people have waited outside the building on line since the morning. A warm-up comedian will spend fifteen minutes or so cracking jokes and prompting the audience on protocol—no talking, texting, or Tweeting on cell phones, no recording the show, and no photographs—as well as the proper way to laugh: outwardly, not the snickering way you might laugh at home while watching the show. And just before the cameras start to roll, Stewart walks onto the stage and takes a few questions from the audience: “You can ask me anything you like, and I will answer you facetiously” is his standard introductory line. During the Q&A session—which can last ten to fifteen minutes—audience members ask everything from how many researchers he has on staff to his honest thoughts about Bill O’Reilly. Occasionally someone will go on a tear about conspiracy theories, but there are a bevy of staffers in the aisles specifically used to cut these rants short.

The show zooms by, and by the time that “Your Moment of Zen” runs, the editors have already begun to cut and shape the episode into a cohesive whole. Stewart runs through a brief postmortem with the staff, which elicits typical comments.

Not everyone can handle the pressure of what is required to make each show, let alone deal with the exacting standards of Stewart. While many staffers have quit due to the pressure over the years, others have decided to leave because of Stewart himself, who “is a man of very high and almost impossible expectations at times, but we try to meet them because we love the guy,” stage manager Craig Spinney cagily replied to a question about his boss’s demeanor behind the scenes.

“It’s a harsh work environment,” said Havlan.

For his part, one way in which The Daily Show does take after traditional news broadcasts is that the role of the anchor is not only to deliver the news but to act as a kind of managing editor in the staff structure.

“The last thing I think about is performing,” said Stewart. “It’s all about the managing, editing, and moving toward showtime.”

Even though the daily deadline could be crushing at times, Stewart admitted that being a fake news show means their deadlines are more loosey-goosey than in a straight news show, while also helping to provide the unique Daily Show twist to a story.

“It’s been exciting to see fake news catching on like that,” he added. “We don’t make things up, we just distill it to hopefully its most humorous nugget. And in that sense it seems faked and skewed just because we don’t have to be subjective or pretend to be objective. We can just put it out there.”

Despite what others say of his exacting standards, Stewart claims he’s perfectly at home delegating much of the responsibility for getting the show on the air to his staff. “I can literally show up at five o’clock pretty drunk, and as long as the show is spelled out phonetically on the prompter, I’ll do OK,” he said. “I just have to face in the right direction.”

After the frenzy and intense focus required to create, edit, and polish a completed twenty-two-minute show every day, the aftermath of the rehearsal and taping before a live audience allows Stewart to let his hair down. After all, the hard work is basically done by the time five o’clock rolls around.

“A lot of times, Jon goes through rehearsals with his feet up on the desk,” said Havlan.

After providing the framework and general guidelines to the writers, editors, and correspondents, Stewart treats them the same way that Comedy Central treats The Daily Show: he gives them a very long leash. “Jon taught me how to do [political comedy] so it would be smart,” said Colbert. “He encouraged everyone to have a point of view and there had to be a thought behind every joke.”

Though the planning, writing, and rewriting can be killer, one feature that Stewart calls the one-to-one is almost too easy. “I’m sure that guy fucking said the exact opposite thing six months ago,” Stewart or a staffer will say in response to a quote from a politician or celebrity in a recent news story. Then a writer or production assistant will be off and running, assisted by TiVo to find the opposite quote that they’ll run back to back. “If you can get a one-to-one with a guy saying the exact opposite of what he said today, then you… giggle.”

While he heaps accolades on top of accolades when it comes to his staff, Stewart has a particular regard for his executive producer Ben Karlin, who came to the show from The Onion, though they do have stylistic differences when it comes to humor. If anything, Karlin’s brand of humor is harsher and more pointed while Stewart prefers to concentrate on the precise combination of words and jokes that will bring the biggest laugh from the audience.

Once he got past the first year, Stewart said it helped to think of the show as doing a twenty-two-minute stand-up routine, where the goal was to fit twenty good jokes into each episode. He admits that’s what makes it relatively easy. “The concept is to come up with a wisecrack every forty-five seconds, [which is] the only thing that I’ve been trained for.”

After producing the show for a couple of years, Stewart had relaxed into a rhythm—perhaps a little too much. Many guests—not just politicians—were often caught off guard by how unprepared Stewart was. When author David Halberstam appeared on the show, Stewart revealed his hand when he was wrapping up the segment. “It’s a beautiful read, and, as always, great to see you.”

The problem: just two minutes earlier, Stewart told the author that he hadn’t even cracked open the book. Plus it was Halberstam’s first appearance on the show, and the first time he and Stewart had met.

“But we’ve never met before!” said Halberstam, at first slightly shocked but then dissolving into laughter.

Stewart later admitted that he felt bad about the interview, but not that much.

In fact, Oscar-winning actress Jennifer Lawrence teased him about his sloppy interviewing techniques when she appeared on the show in the fall of 2013.

“Your producers and everyone involved in the show tell everyone, ‘He’s not really gonna know a lot about the movie or about you,’” Lawrence humorously scolded him on the November 21 show when he admitted he wasn’t very familiar with her current film, The Hunger Games: Catching Fire.

“Normally you have like a pre-interview and you kinda go over like bullet points of things we want to touch on,” she said. “The producers are like, ‘No, no, you guys are just gonna talk. He’s just probably not gonna ask you anything about the movie. He might not ask you anything.’”

True to form, Stewart admitted as much on the air, though he was visibly surprised at being called out by the young actress during taping. “I don’t prepare for these very well,” he said.

But despite the Halberstam incident, Stewart does try to read the books of the authors whom he hosts on the show. “Some weeks we have four books [on the show] and they can be thick ones and [sometimes] historical nonfiction,” he said. “But I read pretty quickly, and I try and read as much of the books as I possibly can. I have a pretty good ability of getting through it and retaining a good deal of its information for a four- to six-hour period.”

Despite the fact that Stewart typically treats non-politician guests in a lighthearted manner, occasionally he turns the tide and becomes outwardly hostile toward a guest. Sometimes the parts don’t make the final edited broadcast—and only hit the news when Stewart later makes an offhanded remark about a past guest—but sometimes they do.

Take Hugh Grant, whom Stewart has referred to as the worst guest he’s ever hosted, adding “and we’ve had dictators on the show.” Grant appeared on the show to promote his movie Did You Hear About the Morgans?, and from the moment he set foot in the studio, the actor became extremely demanding and complained pretty much nonstop. “He’s giving everyone shit the whole time, and he’s a big pain in the ass,” said Stewart. When Grant openly grumbled to some staffers about the movie snippet that would appear during the segment, saying, “What is that clip? It’s a terrible clip!” Stewart let him have it.

“Well, then, make a better fucking movie,” he replied.

The exchange was understandably cut from the final broadcast, but made headlines later on when a reporter asked Stewart about his all-time least favorite guest. And then Grant himself commented on their exchange, actually admitting via Twitter that Stewart wasn’t too far off the mark. “Turns out my inner crab got the better of me with TV producer in 09,” he tweeted. “Unforgivable. J Stewart correct to give me kicking.”

The offices of The Daily Show on the west side of Manhattan were at 513 West 54th Street, before they moved to the new studios at 733 Third Avenue between 51st and 52nd Streets in 2005 because The Colbert Report had taken over the 54th Street facilities. The environment could best be described as a utilitarian office setting with a comedic, almost frat-boy feel to it. A visitor once described it as “a narrow, carpeted hallway with a series of small offices that could be singles and doubles in a freshman dorm.” The doors to each office are typically covered with a variety of small bulletin boards, games, and dolls and cartoon characters, along with a smattering of newspaper stories.

Competition was fierce to get a job on The Daily Show—producers regularly reviewed résumés and clips from writers, comedians, and administrative staff whether they were sent cold or via another staff member—but perhaps it was even more breakneck among college students to land an internship on the show. After all, they were the Show’s most loyal audience. Thousands of applications poured in for the six internships offered each summer on the show.

As a broadcast journalism major at the Edward R. Murrow School of Communications at Washington State University, John Obrien won an internship to the show in the summer of 2002. Most interns came from a comedy background; he felt that his application stood out because of his journalism major. Though he was thrilled at winning the position, he was also warned that his days would be filled with lots of gofer tasks like making copies, messengering tapes, and running all over Manhattan getting props for the show; indeed, on his first day, even though he was unfamiliar with New York, a production coordinator asked him to go to Spanish Harlem to buy a bright orange tank top in size 7-XL at a hole-in-the-wall convenience store. He was also informed that he would have very little contact—if any—with Stewart or the correspondents.

At the time, there were about forty people working at The Daily Show, and Obrien described the working environment as incredibly relaxed. “It wasn’t a pressure cooker at all,” he said. “People brought their dogs to work, there were frequent office parties, and overall, it was very loose,” he said.

Seth Zimmerman interned with Obrien at The Daily Show in the summer of 2002, and he remembers watching Colbert and Carell review a script for their “Even Stepvhen” debate, where each correspondent takes an opposing side of a timely and often controversial subject. Sometimes they’d rehearse it in the interview room, other times they’d go over it backstage.

“It was cool to see the two of them go over an ‘Even Stepvhen’ scene because they made it look like they’d been doing this forever,” said Zimmerman. “They seemed so natural but also so iconic. They were always hitting a button of some kind, and they’d always laugh. Once they got on camera, of course, they’d be totally professional, but beforehand they’d both turn it on and off at will as they tinkered with the sketch. Then backstage, right before they went out, they’d toss a football back and forth.”

Every day, the interns rotated within several departments, ranging from general production to post-production audience, to working even with the writers or in accounting. Mandy Ganis was a Daily Show intern in the summer of 2003. “We were all working in such small quarters, so we got to see everyone all the time and talk with everyone,” she said. “They weren’t big names, they were friendly and laid-back.”

The humor on the show naturally extended throughout the rest of the office, including the intracorporate documents, a weekly newsletter, and the bible for new interns: The Intern’s Guide to The Daily Show. The handbook gave them everything they needed to know for their tenure, and was written with typical Daily Show humor. A job description for each staff member was listed, along with the location of his/her office. For instance, Jon Stewart’s office was located on the second floor, and this was his job description: “Hosts, writes, consults, manages the Bennigan’s off of exit 7 on the Jersey Turnpike.”

Ganis soon learned that when it came to the administrative staff, writers, and on-air talent at the show, the most valuable intern was whoever was the general production intern that day, whose primary job was to buy food to stock the entire office, including the green room, the control room, the writers’ lounge, and the kitchen. The list was preprinted and long, with around fifty different items to inventory and check off before heading to D’Agostino, the supermarket around the block.

The list included the following:

The intern in charge of the shopping was supposed to first check to see if anything needed replacing; if, for instance, there were only two Fuji apples in the house, the intern would buy one more that day.

Food responsibilities were not limited to the general production intern. For the intern assigned to the writers’ lounge, the first order of business was “to bring the writers’ bagel basket up at 9:30 and bring it back down to the kitchen between 10:30 and 10:45.”

The intern’s primary responsibility boiled down to the care and feeding of the writers.

Besides the food, one of the first things that stand out at the studio are the dogs.

Lots of them.

One of the perks of working at The Daily Show is that employees are allowed to bring their dogs to work, which contributes to the somewhat relaxing atmosphere. While not everyone brings their own dog to work every day—including Stewart—at least four or five will be on hand at any one time. Stewart will sometimes bring his pit bulls in.

But it’s not just fun and games. “We all feel this responsibility to keep the dogs pretty well-behaved,” said Jen Flanz, a co-executive producer of the show who is often accompanied by Parker, her Lab mix. “If someone comes in and thinks this is a free-for-all, they would be mistaken.”

Supervising producer Tim Greenberg often brings his rescue Pointer-mix named Ally to the studio, and agrees with Flanz. “Like the show itself, there really is a strict discipline underlying what looks like a free-form,” he said. “This is a giant dog playground. The dogs run around, and there are at least eight to ten treat stations throughout the office. Ally’s got her own schedule of things she does. She gets exercise running up and back. The only thing that would make it better is if there were grass and squirrels [inside].”

According to Hillary Kun, supervising producer and the show’s talent booker, “the dogs loosen up the place. Personally, if I have a bad day, or am stressed, it’s nice having the company of the dogs, to have them come into my office. Dogs are therapeutic.”

“We have animals around to help us relax a little, reminders that you shouldn’t take life too seriously,” added correspondent Wyatt Cenac.

“The dogs that get to work at this office have won the dog lottery,” said Justin Chabot, artistic coordinator and DV shooter.

“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.’”

“There’s a huge discrepancy between the Jon Stewart who goes on TV every night and the Jon Stewart who runs The Daily Show with joyless rage,” said an anonymous former executive.

It was something that Bob Wiltfong witnessed on a daily basis during his tenure at the show, and he blames Stewart’s tendency toward anger as one of the reasons why he only worked there a short time. “When I look at the show now, I can see the anger come out in his comedy, and I’m not like that,” he said. “I’m much more positive about the world. So in a way, I didn’t fit the core principle there.”

Indeed, when it surfaces publicly, Stewart’s anger has seemed misplaced and just a little bit self-righteous. Actor and comedian Seth MacFarlane created Family Guy, among other top-rated comedy shows, and right after the 2006–2007 writers’ strike, he incorporated a brief snippet—a very inside-the-industry joke—into the animated show that ragged on Stewart for going back on the air while the writers were still out on strike. After the Family Guy episode aired, Stewart called MacFarlane and proceeded to scream and yell at him for a full hour, saying he had no right to call him out for that.

“I was really kind of in shock more than anything else,” MacFarlane told Piers Morgan on CNN. “It was kind of an odd Hollywood moment. I was a huge fan of his show, and here I was getting this angry phone call.” MacFarlane added that Stewart then asked him, “Who the hell made you the moral arbiter of Hollywood?”

Morgan then replied, “But not if you’re the self-appointed moral arbiter of Hollywood, which is exactly the position he plays. There’s a certain irony in Jon Stewart ringing up haranguing you for mocking him.”

Then again, perhaps Morgan was just getting back at Stewart for the time a year earlier when Stewart appeared on Larry King’s show on CNN and criticized the network’s decision to bring in Morgan to take over King’s show; after all, MacFarlane was visibly shocked when Morgan initially brought up the angry phone call on his show. Before then, he hadn’t mentioned it publicly.

Even after the first few years, the Daily Show schedule was so relentless and taxing, more than a few staffers wondered how long Stewart could keep it up. “Doing The Daily Show with Jon Stewart is creatively and physically exhausting,” he admitted just six months after starting as host in 1999. Yet, at the same time, he admitted that exhaustion had its benefits.

Our work “is actually enhanced by a certain sleep deprivation, because it’s the part of your brain that you’re not really in touch with until something’s desperately wrong,” he said.

“There are a lot of days when we walk off that show and go, ‘Ewww, we were putrid,’” he said. “I feel like when you watch that show, it shouldn’t look like we’re working hard on it, but we are.”

He’d worked his tail off to get the opportunity to host the show, and once there he’d be damned if he’d let anything or anyone interfere. But even he admitted that sometimes he thought it was too much. “Even if you’re eating delicious chocolate cake, there are moments you feel like, ‘I’ve had too much,’” he said. “Now replace ‘chocolate cake’ with ‘shit taco’ and you know what our day is like every day.”