8

Midwest Midterm Midtacular

Election years always stimulated the show, usually for the better. For 2006, Stewart was looking to beef up the ranks of “contributors”—the comedians who would appear every so often at the desk to offer mock commentary and joust with the host—beyond Lewis Black and Larry Wilmore. The real world was ever more daft: The Bush team had hired an ad executive to sell democracy to the Iraqis, and it had tried to dress up torture by calling it “enhanced interrogation,” when not being openly contemptuous of critics. “They’re living in the tropics,” Vice President Dick Cheney said of the Guantánamo Bay prisoners. “They’re well fed. They’ve got everything they could possibly want.” So one addition to the cast was a man who didn’t fit any traditional Daily Show category—but who had a highly developed sense of the absurd that fit the times.

JOHN HODGMAN

At that point I was already in my midthirties. I was heavier than I am now, and a weird guy, a man-baby with a lazy eye. It did not seem like an on-camera career was really likely. And yet as implausible as it was, Jon made that happen.

JON STEWART

Why did I want John Hodgman as a contributor? Because he’s a fascinating character. A man of substance, a man of flair. You treat him as the bon vivant that he is. When he shows up, you like to have the property minibar with the right ice and the highball glasses he requires. He’s a walking Algonquin round table.

JOHN HODGMAN

The Areas of My Expertise, my first book, had come out. I got a call after a poorly attended reading in San Francisco saying, “Come back east, because you’re going to be on The Daily Show.” As a guest.

That reading in San Francisco was attended by about fifteen people, and my book was, I think, number 16,000 on the Amazon list. Then I went to New York, did the show, flew overnight to Seattle. When I arrived in the morning the book was number seven on Amazon, and the bookstore had attracted 450 people.

Ben called me up that winter and asked me to think about what I might do on the show as a regular contributor. I realized that I could adapt this character that I had developed for the book into an all-purpose authoritative academic know-it-all.

One of the things I said to him was, “You know, you’re constantly seeing on CNN or Fox or whatever, they’ll call in an expert to illuminate some esoteric point, and I could be that expert. And the joke is, whatever it is, I am the expert.”

Jon Stewart: [at anchor desk] The U.S. Army has recently sponsored a civilian-only essay contest called “Countering Insurgency” to solicit ideas from the public on how best to defeat the Iraqi insurgency… Now, it just so happens that there is a Daily Show connection to the contest. One of the judges is our own resident expert, John Hodgman.

John, isn’t it unusual, and perhaps a tad ominous, that the government is turning to the general public for help with its military strategy?

John Hodgman: Well, not really. The nation has been brainstorming this way for cash and valuable prizes since our beginning. Our national anthem? The result of a jingle contest. The decision to drop the atomic bomb? That wasn’t Truman, but sweepstakes winner Penny Holcomb of Palm Beach. And for that she received a case of Lucky Strikes—and a lifetime supply of sadness.

Jon Stewart: What would be an example of a good essay?

John Hodgman: When it comes to writing an expository essay about counterinsurgent tactics, I’m of the old school. First you tell them how you’re going to kill them. Then you kill them. Then you tell them how you just killed them. That’s why I like this idea I read from Jonathan Colton of Colchester, Connecticut. He thinks we should drop thousands of king cobras into Fallujah—each equipped with its own little parachute, of course. It’s simple, direct, elegantly written. Not to mention the whole snake-sized parachute industry is going to get a huge boost out of it.

JOHN HODGMAN

There’s no question that breaking a taboo elicits laughter, right? The truth about what was happening in Iraq, and what was happening in terms of media coverage in Iraq, had become so taboo that it had become funny. The Daily Show wasn’t satire. All Jon was saying was the truth.

And particularly in the first half of the last decade the truth was hard to come by. Indeed, there was a lot of pressure to not say what was plain on its face. I mean, this was Ari what’s-his-name telling Bill Maher, “Watch what you say.” That if you didn’t conform to the narrative you weren’t an American. And this boiled the blood of everyone in this country who didn’t feel part of the narrative.

For someone like Jon—and I think for a lot of people like him who are profoundly interested in the experiment of America, and the history and the culture of America—to have that essentially taken away just because you had some questions about this idiotic and loathsome war, well, it really made a lot of people feel utterly in exile.

The 2006 midterms motivated a weeklong trip to middle America, to Columbus, Ohio. The Buckeye State had basically decided the previous presidential election in favor of the incumbent, George W. Bush. That alone made it an intriguing backdrop for The Daily Show. But the choice of a politically purple state, near the middle of the country, made metaphorical sense, too. Fox News and MSNBC played to audiences on the right and left wings. Stewart and The Daily Show were, more and more, becoming the voice of the quieter, busier, more rational middle of the political spectrum.

The search for an answer was conducted in true Daily Show fashion—on the first night of the trip, correspondents Bakkedahl, Bee, and Jones reported from in front of three different Applebee’s locations, while Riggle claimed to have located the “real” Ohio at a Bob Evans.

But the lessons about America’s complicated heartland values were especially vivid for The Daily Show’s newest correspondent.

JOHN OLIVER

I’d been in America three months. I went out ahead of the rest of the show, to shoot a piece in Chillicothe, Ohio. That was the first time I’ve seen a gun in the wild. We were at a diner, and a guy pulled up in a truck and there was a rifle in the back, and I’m thinking, “Holy shit.”

You don’t see guns anywhere in England. No. In Chillicothe, the guy absolutely refused to believe that I had never seen a gun before, and that I had never fired one. He swore I was lying. He offered to let me shoot his gun in the parking lot. I very much refused that offer. I’m thinking, “This cannot be my first time, with some random farmer in Ohio. It’s got to mean more than this.”

Six years into the Bush Administration, the run of bad news was wearing on nerves—in civilian life, of course, but also inside The Daily Show, where digesting, in Stewart’s words, “the shit taco” was what everyone did for a living.

Karlin had mellowed somewhat since his bruising first years as head writer, but his hard-driving style as executive producer, a crucial factor in creating a top-notch show four nights a week, had frayed some relationships.

ELLIOTT KALAN

Ben was very much the executive producer the show needed at the time, when he replaced Madeleine. But he was also a much brusquer person than it would have been nice to have had. He gave Jimmy and me a real shot, recognizing us and moving us up. Outside the show he’s always been supernice to me and very gracious and very helpful. Ben is like Shaft. He’s a complicated man.

JEN FLANZ

Ben is creatively very intense, and he was also young. He was taking on a lot, managing people.

He was hard on me. Yeah. Absolutely. Yeah, there were days I cried. Ben and I had crazy fights. But we always made up. I would go back at Ben like an older brother. Every few months we’d have a blowout.

But Ben at a party is great, and he started “summer fun day” at the show. And I learned a lot from him. There were a lot of people Ben didn’t like dealing with—and there are a lot of people that just didn’t want to deal with Ben—so he came to me for a lot, which ended up giving me a lot of opportunity.

RORY ALBANESE

I don’t think the show would have become what it did without Ben. He was integral in taking it from this little basic cable thing to a juggernaut. He didn’t ever lose sight of the goal of making the show great.

I don’t think Ben was ever a mean guy. Sometimes he was curt. But people who work in TV are entitled and they’re babies.

ERIC DRYSDALE

It’s funny, I was thinking about this. I remember leaving work and burning with hatred for Ben, but I don’t remember why. Insofar as his job was to protect Jon, he did a great job. And I think that he did that at the cost of morale among the writers.

DAVID JAVERBAUM

Ben had weather, and sometimes the weather was worse.

BEN KARLIN

That stuff really was a function of the transition to Jon being the new host and me being the new head writer and how much that shook up the status quo. Once we got into a groove, around 2001, there were quite a few consecutive years where I felt good about my relationships with 95 percent of the staff—writers and otherwise. After that, any tension or bickering or “weather” was mainly over production issues—missed deadlines, lazy scripts, graphics that didn’t work, field pieces that would never seem to come together despite so many hours put into them. Producing that show was a motherfucker and it could get the best of you. Sometimes it did, and there certainly were times I wish I handled it with more grace and civility. I’m sure there is a platonic ideal of the showrunner—one who is creatively vital, in full command of all aspects of production and also beloved by all their employees and coworkers. I wasn’t it. Maybe Jason Katims? He seems like a great guy. For real.

Karlin and Stewart had remained an effective creative duo. But in 2010 the grind and conflicting ambitions severed that bond, too.

JIM MARGOLIS

Jon and Ben were developing movies and TV shows together, then something happened between them and all of a sudden it just all went black.

JON STEWART

Ben got married in Italy that spring, and Tracey and I had a baby, I don’t know, a month before, so I didn’t go to Ben’s wedding, and I think that bothered him a little bit. Then he didn’t come back from the wedding, and that bothered me a little bit. And he didn’t call me. Ben called somebody else who delivered the message that he was going to be gone two more weeks, and I was like, “In what world are you allowed to do that?” Ben says, “Well, I thought that I’d earned it from all the things we’ve done.” I was like, “You may have if you had said to me, ‘I’m taking a month off.’”

This felt different. Basically he was ready to be his own boss, it was clear.

BEN KARLIN

We’d done the book, then I was executive-producing two shows and planning a wedding in another country, and I was ground down to a nub. I’m bike riding in Sardinia, and I’m like, “Why the fuck do I want to go back to New York right now?” I made an extremely poor decision, in the throes of a new marriage and love.

JEN FLANZ

The tensions between Jon and Ben had been growing over time. But when we went to Columbus for the midterms in October, you could really see it. I’d be going to check in with Ben, touch base about some of the visuals for the show, and be told, “Oh, he went out for a walk.” I’m like, “Fuck, that’s weird.” Ben never went for a walk.

BEN KARLIN

I was excited to be in Ohio. We had LeBron James on the show. But it was just hard.

JON STEWART

Any time you travel, any kind of fragility or cracks in the process or in relationships is going to be amplified by the lack of sleep, by the stress of not knowing where the copier is. But I was digging Columbus. Why not put a little cheese on something? Very nice people, very accessible, and basically anything Alfredo. You can’t go wrong with that.

I could see Ben was really angry, and it was bothering me. I’m thinking, “I don’t want to feel like I have to convince somebody that this show is a great place to be,” and in his mind I imagine it was, “I don’t want to have to fucking listen to you.”

BEN KARLIN

There was a lot of fatigue. We had launched Colbert and I was really wearing two hats. That brought a lot of added pressure. Jon was very adamant about not raiding the mothership for the satellite. As much as we all loved, supported, and wanted Colbert to be a hit—and Jon was the executive producer of The Colbert Report—Jon really wanted to keep as much of a separation of powers as possible with The Daily Show.

JON STEWART

Unfortunately at The Daily Show, ultimately there’s always going to be a block to your creative input, or to your fulfillment, and it’s going to be a Jon Stewart–sized block. You had Ben with a sense of mounting frustration over a role that he didn’t necessarily want to continue to fulfill because he had grown beyond it, and you had my frustration at needing someone to fulfill a role that was really crucial at the show.

BEN KARLIN

I just loved working with Stephen. I love him as a man, as a friend, just as a person, and his show was really, really exciting. Jon was a standup for so many years and he was able to find the joy every day in going out and doing material on The Daily Show. As a nonperformer and as a writer, I didn’t have that same joy. I kind of sadly needed something new, and Colbert was something new. So I was very conflicted about where I knew my loyalty should be and where my heart was.

JON STEWART

After we came back from Columbus, that final conversation in my office was very hard. It was very hard.

BEN KARLIN

Superpainful. For the seven-plus years of our collaboration we were pretty much in lockstep. It was an incredible ride. What makes Jon great is he’s a savvy and smart businessman and he knows how to protect the things that are most important. He worked too hard and too long to build the show into what it was, and he kind of recognized something that maybe I couldn’t see.

Given the history and the nature of our relationship, I was kind of thinking that it would be something that we would plot out over a period of several months. I remember Jon just saying, “No, I think it’s better to just cut it clean.” That was kind of, I don’t want to say shocking, but it was definitely disappointing.

JON STEWART

I absolutely did consider Ben a friend, and still do. But beyond that I’m not particularly close—I’m close to my family, in general, and I have friends, and I’m close to them, but probably not in the traditional way that people assume friendships are like. I’m not a big hangout guy. When I say we’re friends, we’re friends, but it’s not like we summer together, or we went out to dinner every week. I don’t really do that with anybody.

STEPHEN COLBERT

Ben and I have remained friends. What’s between Ben and Jon is between Ben and Jon.

JON STEWART

Ben was the master of the grand polarities. He could be really rough on people, and then he could be really generous with people, and you weren’t quite sure where you were at. But you don’t want that to take away from the fact that he was incredibly gifted, and an enormously crucial part of making the show what it was in those early years.

The suddenness of Karlin’s departure, on top of Javerbaum’s impending, voluntary exit, could have left a large vacuum in the show’s day-to-day creative management. So Stewart moved aggressively to fill the hole before it could cause damage. What was a good short-term solution for The Daily Show, though, ended up fracturing a long-running friendship.

RORY ALBANESE

The change was shocking. D.J. was supposed to leave, and then all of a sudden Ben got fired and D.J. was staying. It was weird, and then it got very odd, because D.J. clearly didn’t want to be there anymore. He was done, he was burnt. He had said, “I’m gonna do Broadway, I don’t want to be here anymore.” And now this guy’s in charge.

BEN KARLIN

The writing staff had thrown him a going away roast, at Keens. Then it became clear I wasn’t going to be coming back to the show. Jon reached out to D.J. and asked him to stay. D.J. told me that he wasn’t taking the job, and then I came in to find out he had taken the job. Jon would have survived it no matter what because he’s incredibly talented at this, but it was definitely the smart move. I didn’t begrudge Jon for it at all. To lose your number one and your number two producer, without even a remotely clear number three, would have been really, really tough for a show like that.

D.J. was one of my oldest friends. I had known him since I was sixteen years old, and I had hired him at the Onion and I had hired him at The Daily Show. I fought for him to take over as head writer, and I had really done right by him. I don’t have an ax to grind with D.J. I have a disappointment and a measure of heartbrokenness over how our relationship kind of came to an end.

DAVID JAVERBAUM

Ben never forgave me for that, and he thinks I was disloyal and thinks I handled it poorly, and I probably could’ve handled it better. Yeah, that was an awkward thing, and I don’t like the fact that this person who was my best friend for many years and to whom I owe my career and I are so estranged.

The changes weren’t limited to the lineup of writers, producers, and correspondents. The Daily Show was, and always would be, at heart a comedy. But its humor darkened as the outside world continued to serve up bleak events: the ongoing disintegration of Iraq, the beginning of the subprime mortgage crisis, the Paul McCartney–Heather Mills split. The sharper focus on politics and media, and Stewart’s greater control of the creative process, spurred tensions and changes in the Daily Show ranks.

CHRIS REGAN

When I started on the show, there was a lot of pop culture stuff, a lot of celebrity stuff. After the 2000 election, after the 2004 election, we abandoned all that for hard news. We heard the dreaded “point of view” phrase bandied about all the time.

I didn’t get into comedy to talk about one thing over, and over, and over again, that being American politics. So I was pretty over it, and I think they were pretty over me. I went to Jon and I told him I was burned out, and he said to me, “You’re burned out? Walk in my shoes one of these days.” It was the most candid he’s ever been with me, just going on about how he’s up all night, looking online, trying to find a new angle. “Am I a comedian anymore, am I a journalist?” He went on for about six or seven minutes, telling me about how he was having trouble keeping it fresh himself. In seven years, we had never had a conversation that candid.

And at the end I said, “Okay, good luck.” I left The Daily Show. This was somewhere in 2006. Jon somehow found a way to keep it fresh for nine more years.

JON STEWART

We were feeling around for a new direction. The one thing I couldn’t change was my brain. I’d given up drugs largely by that point and booze, mostly. So all I had left in my life was conversation. After Ben left, we brought in Josh Lieb and Dan Sterling and David Feldman as producers from the outside. It was about creating new nutrients, new avenues, new people to view things with a different eye, because the one thing I always felt confident in is my ability to recognize a good idea.

STEVE BODOW

That was a weird time. I had moved up to being head writer and took the job thinking that I was going to be working for Jon and for Ben, and then their falling-out occurred, and suddenly I was going to be working for D.J., who explicitly had expressed no interest in being a manager. There was nobody around who was senior at a producing level, so Jon brought on all these other people from the outside. That’s not an experiment that’s really been repeated.

Two of the new producers, Sterling and Feldman, had fairly brief runs—Sterling leaving to run Sarah Silverman’s new show, and Feldman less amicably. The third, however, became a beloved and instrumental presence inside The Daily Show.

JOSH LIEB, executive producer, 2006–2010

I’d grown up as a kind of hippie kid in Columbia, South Carolina. I like the old Mad comics, and dialect humor—The Education of H*y*m*a*n K*a*p*l*a*n. Charles Dickens is my favorite comic author—the very human failings. As a kid I watched Laugh-In reruns any chance I could. And WLTX from 11:00 to midnight every night was Sanford and Son and Andy Griffith reruns. Then I’d gone to Harvard and written for the Lampoon.

In 1994 I applied for a job as a writer on the new Jon Stewart Show, on MTV. I was such a cocky little son of a bitch. When they offered me the job I told Jon that I’d only take it if I could sing “Suicide Is Painless” on a test show. And I have no idea where that came from. So there’s a test show somewhere out there with me singing, my friend Brian Kelly playing ukulele, and we’re in Army camo fatigues. It’s awful. But anyhow I took the job, and it was great. Then I did four seasons as a writer and producer at NewsRadio, and one season at The Simpsons.

I was a completely LA guy. And I got a phone call one day in 2006 from my agent asking, “Would you be interested in going to work at The Daily Show with Jon Stewart?” It was bizarre to me to think of going back to New York. But a lot of it was that I would love working with Jon again.

And I will say this. When Jon took the Daily Show job, I thought that was the stupidest thing he could’ve done, right? I thought it was idiotic, and I said that very loudly to a lot of people. Because at that time The Daily Show was just this crappy little cable show. I didn’t watch The Daily Show very much in Jon’s first few years. But I knew by the time I came back that he had turned what was a good but standard show into a special show.

RORY ALBANESE

Working with Josh Lieb, those were some of the best years of my life. He’d show up to work and call me and say, “Hey, can you come down and bring me money for the cab?” Josh would be in the back of the cab, reading a newspaper, holding a mug of coffee—not a travel mug, a kitchen mug. I’d do the backstory: “Let me retrace your steps. You poured a cup of joe, grabbed your paper, no wallet, walked outside reading and drinking, hailed a taxi, pulled up to work and realized you didn’t have any money, and called me?” The guy probably owes me a hundred bucks.

ELLIOTT KALAN

There’s certain guys who see the matrix in comedy. D.J. is one. Josh is another, where you feel like they can go into bullet time. They see a joke—they see the construction of it completely. They know it backward and forward. And he was just so much fun to work with. I remember Josh pushing Snarf as Jon’s cohost for a week. Half seriously.

JOSH LIEB

I wasn’t half-joking! This was a real pitch! It was a joke based on the feeling that we were never as good as a network show. When you’re on basic cable, no matter how successful you are you always feel like you’re in the ghetto a bit. So the joke was Jon would finally have a sidekick, but that the only one Comedy Central could afford was Snarf, from the ThunderCats cartoon.

Like, how annoying would it have been for Jon Stewart to have to deal with Snarf as a sidekick? Like, “What do you think of Dick Cheney, Snarf?” “Dick Cheney! He’s a jerk! Snarf, snarf! He makes me feel bad! Snarf, snarf!” It could have been huge. Could have been a spinoff.

I can’t believe anyone remembers that but me. It makes me happy.

JON STEWART

Everyone needs a little Lieb in your life. He wasn’t a prick, he wasn’t cynical, he wasn’t haughty, he was just smart and fun to be around. He’s a guy who will put away three martinis at the Friars Club while wearing pants that match the weird wallpaper, but he also scours white supremacist websites to see how the interesting Jewish conspiracy theories came about. He’s just so… Liebish.

RORY ALBANESE

There were always a lot of bits, running jokes, when Josh was around. There was an ongoing bit where Lieb was getting threatened by various people. You’d leave a note on his desk: “Josh, you’ve got a phone call, it’s David Remnick and the message is ‘I’m going to kill you.’ Please return call.”

JON STEWART

It was always from famous people, like Tony Danza sending really threatening letters to Josh, and they would just appear in places around the office.

Josh walked into a very difficult situation in that he was coming in at a position of responsibility without having been through the process of the show. Generally people were promoted from within there. We tried it maybe three times, to bring in outside people, and it’s worked once, and that’s Josh.

JOSH LIEB

I think my great utility at The Daily Show might have been in telling people, “Hey, this doesn’t need to be changed. This is working.” They didn’t know how good they were.

The Daily Show didn’t have any Lampoon writers, except for D.J. and me. We did tend to get more writers who had come out of the magazine world—Bodow, Daniel Radosh. Radosh and J. R. Havlan both had an incisiveness and sort of a mordancy. There’s no place too dark for them to go. Rachel Axler, out of the playwriting world. Rachel, like Rich Blomquist, has a great insanity where the jokes would come from a place you could not have imagined. Sam Means had a bit of a gentle weirdness. Rory could give you any kind of joke but he could also give you the straight-ahead joke, the “Let’s cut through the bullshit, what are we really talking about here?” joke that we frequently needed to end a piece.

The first big meeting of the day was all of the writers and producers going, “Did you see this? Did you hear about this?” I had a whole chain of people who didn’t just find the obvious stuff in page A1, A3 of the Times stories. Tim Carvell would have watched Fox & Friends every morning for whatever goddamn reason. Nobody assigned him to it. He’s a sociopath. Everybody, whether writers or researchers or second producers, had their eye on something and everybody was saying, “God, at 6:15 last night on NBC Nightly News you should have seen…” or, “At 5:15 this morning on MSNBC, you had to see it,” and they would have the tape and bring it up.

Lieb’s eccentric energy was welcome after Karlin’s more muscular style. So, too, was the onset of a new, Bush-less presidential campaign season. By early 2007, a mere seventeen candidates had declared, a coalition of the ambitious including Mike Gravel, Mike Huckabee, John Edwards, Ron Paul, Evan Bayh, and Duncan Hunter, sparking one of The Daily Show’s most apt rubrics: “Indecision 2008: Clusterfuck to the White House.”

Jon Stewart: [at anchor desk] Let’s start with the GOP, where the front-runners include a conservative, [shot of John McCain] a Mormon conservative, [Mitt Romney] an evangelical conservative, [Sam Brownback] and a New York liberal conservative. [Rudy Giuliani] My money’s on the white guy.

Across the aisle, the Democrats are fielding a veritable rainbow coalition. A win for any of these candidates would make presidential history. Be it the first female president, [Hillary Clinton] the first African-American president, [Barack Obama] the first Latino president, [Bill Richardson] the first leprechaun president, [Dennis Kucinich] or the first mimbo! [John Edwards]

The overcrowded field for a wide-open job was a comedy blessing. Keeping up with the glut of material, though, was still incredibly labor-intensive, and finding the clips that would become famous was still a remarkably free-form process.

RAMIN HEDAYATI, from studio production staffer to field producer, 2007–

At that time LexisNexis was our search tool, and you only had a couple blogs that were flagging big moments on cable news—Crooks and Liars, Media Matters. We had about thirteen, fourteen DVRs, and they would only hold about a week or two weeks’ worth of footage. So if we wanted to save anything, we had to manually put a tape in, a big beta tape. Nothing was assigned. People liked certain shows. Jimmy Donn really liked to watch O’Reilly. I would DVR the nightly news, and Special Report with Bret Baier, and a couple morning shows. People always think, “Oh, you guys must just sit in front of Fox all the time,” and it’s not true. You see something and think, “Hey, I should bring this upstairs to the meeting.”

ELLIOTT KALAN

I noticed that CNN went to the trouble to fact-check an SNL piece. And then Jon Kyl, the Arizona senator, was on CNN and said something wrong, and the reporter goes, “Well, we’ll have to leave it there.” So we looked for clips, and CNN did this routinely—they didn’t fact-check their own guests, they just said, “We’ll have to leave it there.”

If you look at the entire show over Jon’s run, and how it evolved, everything it did, from going after CNN to going after the Obama Administration, yes, we were against war and for good things. But the larger theme was truth and not abdicating responsibility for the words you use. And we did a segment about “CNN: Nobody leaves more things there.”

RAMIN HEDAYATI

I produced it. I think Jon’s joke was, “Don’t leave it there. There is a terrible place to leave it! You’re just starting to get into some substance! You have twenty-four hours. Hash it out! There’s nowhere to go. There’s nothing else to do.”

What was cool was that when we would find a trend or some kind of contradiction, that was a victory. Now when something crazy happens on CNN, there are five blogs that flag it. Back then, it was either us or no one.

ANDERSON COOPER, journalist, CNN

I don’t have any specific examples of stuff where I thought The Daily Show was unfair. There’s definitely times I felt like CNN came under greater scrutiny than a lot of other folks who are out there. But criticism can be a healthy thing, and I think it’s good to have someone mock you with some regularity. I can’t tell you how many times I would be in a newsroom and I would see something on the air and then think, “Okay, well, that’s going to be on The Daily Show tonight,” like when I was interviewing Louie Gohmert and he just starts yelling at me.

I think Jon was able to get at some truths mainstream outlets don’t. And I was envious of The Daily Show’s ability to find old videos and mine old statements where politicians contradict their current positions.

I also appreciated, during the Egyptian revolution, when I got punched around a bit, Jon played the video of the attack and said something very funny about, “If they harm one hair on his head…” It was not a great time where I was—I was hiding out in the hotel in Cairo—and someone texted it to me and made me laugh. It was a nice moment.

The Daily Show’s second-floor tape library was now deep with cross-referenced footage, and the show’s graphics and editing software now allowed a five-minute segment to rapidly cut between multiple clips and over-the-shoulders. The process was often hectic, and depended on the talents of dozens of staffers, but Stewart kept close watch on all the moving parts.

JOHN OLIVER

Jon’s saying is, “If you take your foot off the throat of the show for a second, it will just get up and walk away.” And that is true. Like, if you lose focus early in the morning, that lost focus will come back to bite you hard in a few hours, and by that point, the show may be irrecoverable, just because you weren’t focused enough at nine in the morning.

We end up sounding evangelical in a certain way, talking about “the Daily Show process.” You sound like you are trying to sell Scientology equipment. But Jon taught people to do a version of their job that the whole machine needs.

LAUREN SARVER MEANS, from intern to writer, 2003–

There was also a great evolution to the writing process, because when I first started working at the show as Ben Karlin’s assistant in 2005, the writers would have their morning meeting and watch the clips. They’d write a pass of jokes without really a story line, just loose jokes off of sound bites. Turn them in. There would be a joke pick, and then D.J., the head writer at the time, would assemble them into a headline. There was very little room for collaboration with studio production. And as time went on, Jon started shaping studio production to be a huge generator of content, and ideas, and jokes for the show, but he’d want the writers to shape a story line. He wouldn’t just want a page of jokes. He wanted them to tell a story, too.

The writers could have their hands on something and have ownership of it a lot more than just handing in your jokes and being done with it.

DANIEL RADOSH, writer, 2009–

So much of the flow of the day, for me, is just those kind of small, weird moments that you probably get at any office, but just the more extreme version of them in an office of comedy people. We would always end meetings with watching YouTube videos. Jason Ross would be like, “Okay, well, I found this video of a hunter and his girlfriend having sex on top of the body of a dead bear.” We’d watch and then we’d say, “Okay, now, let’s get back to writing!”

After the morning meeting you had a really tight deadline, an hour and fifteen minutes to turn in a script, often out of nothing. It was the most stressful part of the day for me. But I learned, early on, that it was not that important to Jon that the first draft script be perfect, because he would figure out how he wanted to say it, and it didn’t matter, at all, even if I had the perfect way of saying it. Jon was going to say it the way he wanted to.

JUDD APATOW

When you’re in charge and have the final say, you’re constantly rejecting people’s ideas, all day long, and it’s tough to do that in a way that keeps people really encouraged and positive. When I was executive producer at The Ben Stiller Show, I used to sit in my office reading management books trying to understand where the dynamic was going wrong. Jon, at The Daily Show, set up the exchange of ideas so people felt supported and believed in enough that they could really knock things around productively.

JON STEWART

Garry Shandling taught me about intention. Intention is a really big thing at The Daily Show. We always want to know where’s the intention, and now, let’s find a path to that intention.

A lot of my day is finding the writers enough time to bring what’s great about their writing to the process. You sort of come in and you go, “Here are my notes,” and then you leave. The meetings with me did not last long, but hopefully they were edifying. Because I know at four o’clock, I’m going to need to go down there, rehearse the show, drink two espressos, take a handful of chocolate, and pace, and get it to as refined a place as it can be.

In early April 2007, Stewart made a major cosmetic refinement: The Daily Show set that had been installed less than two years earlier was completely overhauled. “The old set, a lot of people had written in and said, the old set, oh, uh—sucked,” Stewart said, smiling happily from in front of a warm blue world map, with a flashy news zipper and a spinning globe blinking overhead. “And as it turned out, you were right. So our experiment in postmodern, neorealist, Waiting-for-Godot-fake-news-show shit is over.” The only design mistake was that the new set included the giant head of Brian Williams.

The guest chair on the retooled set got a workout from presidential contenders. Senator Barack Obama’s first in-studio conversation with Stewart wasn’t terribly memorable, though his exit stuck with one Daily Show segment producer.

ELLIOTT KALAN

There was a line of people waiting to shake Obama’s hand as he left, and when he got to me, I was eating a fun-size bag of Doritos and my hands were covered with orange crap. And I said, “Oh, I’m sorry, I have Dorito dust all over my hands.” Obama very quickly said, “Well, how about one of these?” and he put his hand into a fist and we fist-bumped instead.

No, we did not blow it up. If he had played that, I think I would’ve lost a little respect for him: “All right, that’s too far. We don’t have that kind of relationship, Mr. Senator.”

John McCain’s April 2007 visit, however, was stormy. Three weeks earlier McCain, as part of a congressional delegation inspecting the progress of the troop surge in Iraq, had visited a market in Baghdad. Mike Pence, then a congressman, described the scene as being as safe as “a normal outdoor market in Indiana in the summertime”—while military helicopters hovered overhead and a hundred American soldiers in Humvees secured the perimeter. McCain, preparing another bid for the Republican presidential nomination, then made his eighth and most contentious visit to the Daily Show studio, attempting to defend President Bush’s floundering Iraq surge.

SENATOR JOHN McCAIN

Jon and I had gotten along very well for many years, and then I went on one night and basically he just launched on Iraq and didn’t let me respond.

Jon Stewart: I’m just gonna walk through the talking points, and you tell me why they’re right. “If we don’t fight and defeat Al Qaeda in Iraq, they will follow us home.”

Senator John McCain: Sure.

Jon Stewart: Now my position is—

Senator McCain: Why don’t you read what [Abu Musab al-] Zarqawi said and what bin Laden said. Go online, go on the Internet, they’ll tell you that. I’m not saying it, they’re saying it. Then I can refer you to their statements. Their statements.

Jon Stewart: But also, their strategy is to trap America in a war that will bleed them of treasure and lives. That’s also their statement, so you can go both ways on that. But my point is, Al Qaeda—

Senator McCain: I know one way to go, and that is Al Qaeda has declared their dedication to the destruction of everything we care for and believe in. I know that for a fact. Do you know that for a fact?

Jon Stewart: Whether we’re in Iraq—I do know it for a fact.

Senator McCain: Good. That’s the first time we’ve agreed—thank you!

Jon Stewart: That’s not true! Here’s the thing that I’m trying to say. When [the Bush Administration] attacks people who disagree with their policy, they attack them in that they don’t understand that there’s a real threat out there. The American people, or at least the ones that I get on the subway with, they know there’s a real threat out there. They feel like Iraq lessened our ability to fight that threat.

Senator McCain: The war was terribly mismanaged. It was terribly mismanaged. We are where we are now. And the question is, can we give this strategy a chance? A chance to succeed with a great general.

Jon Stewart: If the architects that built a house without any doors or windows don’t admit that that’s the house they built, and continue to say, “No it’s your fault for not being able to see into it,” then I don’t understand how we’re supposed to move forward!

SENATOR JOHN McCAIN

I have debates with people every day on the issue of national security policy, but I just feel that it’s appropriate for me to listen to their point of view. I just didn’t think it was fair, that interview. I know Jon felt very strongly about Iraq, and I felt very strongly about it. One of my sons, a young marine, was fighting over there at the time.

JON STEWART

I remember the moment in that interview when I realized it was over between me and McCain. We were arguing about the war and he wasn’t looking at me, he was looking here. [points to middle of forehead] And I realized, “Oh… so this conversation has ended and it’s never going to pick up again.”

SENATOR JOHN McCAIN

That interview obviously had a chilling effect on our relationship.

JON STEWART

It was a breaking point of his ability to tolerate me and of our ability to pretend that he hadn’t been one of the architects and promoters of a grand catastrophe.

SENATOR JOHN McCAIN

After the terrorist attacks in Paris and California in 2015, yeah, I feel vindicated on what I said to Jon about why we needed to fight in Iraq. But I wish I wasn’t. Lindsey Graham and I were over in Baghdad three weekends ago, and I can tell you the dominant influence right now in Baghdad is Iran, and that’s not good. It’s not good.

JON STEWART

I was disappointed in him. Fairly or unfairly, I felt that McCain was ignoring a reality for a political purpose. That interview was at the height of the anger over the mess that we had gotten ourselves into in Iraq, the cost that the country had paid, the cost that the Iraqis had paid. It was hard for me to see a guy who I respected for his ability to occasionally speak hard truths sit there and, in the parlance of that great truth teller Judge Judy, pee on my leg and tell me it was rain.

Perhaps I’m giving him more credit than he deserves, or believing something about him that is maybe not the case, but if McCain had not made political calculations in the way that he did with the war, I think he would have ended up in a better place in the 2008 election.

JOSH LIEB

People give Jon shit and claim he breeds cynicism. He’s the opposite of cynical. He really cares. And people who watch his show care about politics. That’s why you watch it, and that’s why you’re not watching a Yogi Bear cartoon.

And Jon created the least cynical place I’ve ever worked. There was a note in the Daily Show staff kitchen, something like, “Your mother doesn’t work here…” And any other place I’d worked I would have written, “Fuck you.” I’ve worked in some pretty rough little comedy places.

And I realized when I looked at this piece of paper it was dusty, and weathered, and barely hanging in there. It had been up there for a long time, and that nobody had written any graffiti on it, and that this was a nice place, and that I didn’t need to be the asshole who came in and was immediately defacing things. I did deface some other things later. But The Daily Show was a very nice place. Which is part of why the writers strike was so painful.