Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  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 fir
st 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:

  • Three boxes of cookies for the control room

  • Three bags of candy for the green room

  • Soy milk—vanilla if they have it

  • Seven blocks of Philadelphia cream cheese

  • Three Fuji apples

  • Three boxes of Kleenex (unscented)

  • Lucky Charms EVERY DAY

  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.