The Daily Show had come a long way from begging its way onto McCain’s bus in 1999. Now an ad blared that Stewart had assembled “the best campaign team in the universe ever,” headquartered it in “the Daily Show news-scraper: 117 stories, 73 situation rooms, 26 news tickers,” and promised to deliver “you all the news stories—first… before it’s even true.”
It was a joke, mocking the show’s stature, and it wasn’t. In 2008 the combination of talent, on and off camera; the gravity of the issues facing the country (a giant recession on top of the worsening Iraq morass); and the vivid cast of candidates (Barack Obama! Hillary Clinton! Dennis Kucinich! John McCain! Alan Keyes! Ron Paul! And introducing… Sarah Palin!) came together to produce twelve months of consistently extraordinary shows.
The hype that had been building about The Daily Show’s influence, The Daily Show being where young people get their news—I think that’s why in 2008 we went with, “The Best Fucking News Team Ever” as the slogan. Let’s stop pretending that no one watches the show, let’s stop pretending that we can’t do some great shit, and let’s just own it. It was actually Jon saying, “Let’s just go hard in the other way.” Like, fuck CNN, fuck Fox, fuck MSNBC. We’ve got a skyscraper! We’ve got a news rocket! We have Riggle firing a machine gun!
Jon was really adamant about keeping up with the pace of the media that we were making fun of. So instead of being satisfied by sticking with some Not Necessarily the News–type format, he wanted to make sure that our graphics were just as good as Fox’s graphics. We had planes flying. Anything on the screen could explode at any minute.
There had been so much talk that when the Bush era ends that Jon’s relevance is going to end, which was simply not true. We all knew that our job wasn’t to make fun of one political party or a political person.
Indeed, after eight years of flaying Bush, Stewart and the staff relished the chance to defy expectations and challenge both sides. But even though most of the major candidates saw The Daily Show as a key platform to sell themselves, Stewart and staff didn’t overestimate the show’s significance.
Probably to me some of the most fun I ever had on the show was when we went against people’s expectations. Because it was like, yeah, we’re not just chumming the waters. Dick Cheney is like Darth Vader—we get it. Move on.
We went after Hillary in ’08, during the primaries. The studio audience thinks Jon is our liberal guidepost through all things, and Jon would do a segment about what Hillary is doing wrong and the audience didn’t know what to do. And there is a weird standup component to it. There’s a Bill Hicks component to that where you’re like, “Oh, you’re going to leave? Then leave.” And it feels kind of good sometimes to say stuff to people that they don’t want to hear.
I’d go up to the desk to talk to Jon between acts, and we’d be like, “Man, these motherfuckers are so pissed. This is awesome!” We have a very left-wing audience and they’d be like, “This is not right. It’s only funny when the jokes are about the guy we hate.”
The problem is everyone thinks it’s funny until it’s something they care about. If you can’t even look at yourself and laugh… It was really powerful for me to watch an audience deal with that, and who better to deliver that information than Jon Stewart? And after eight years of Bush, there was something very fun about going after the savior, going after Obama.
You know, we had presidents on the show. We had all these different people. Didn’t matter. We were always in the bubble and I think in a healthy way.
The staff, we just wanted to go in and write jokes every day. It was trickier for Jon to constantly be asked, “Oh, do you think the show is important?” and having to do this song and dance about how we’re just doing a dumb comedy show. Deep down Jon probably knew that the show was having an impact and was important in a cultural way, but that’s a hard thing to speak to when you’re the guy on camera.
I don’t know how much of what we did changed anybody’s mind and I’m very leery of judging anything like that. But working with Jon, who had a voice in that conversation that year? No, it’s exciting. You get spoiled in this business where words you say, words you write, get spoken to millions of people on a nightly basis, and repeated, and put on YouTube. So there’s an echo chamber. But there are a lot of echo chambers out there.
Obama upset Clinton in the Iowa caucus, then Clinton rebounded by winning disputed primaries in Florida and Michigan. Super Tuesday tightened the race even more, just before Stewart and the writers headed out to the Oscars. On the Republican side, McCain had dispatched Mitt Romney, though Mike Huckabee hung around into the spring.
On June 3, Obama clinched the Democratic nomination. The Daily Show’s newest correspondent, Wyatt Cenac, made his debut that same night. The specific synchronicity was an accident. But the fact that The Daily Show hired its first black correspondent just as a major party was on its way to choosing its first black presidential nominee was not.
No, it wasn’t coincidental, in the same way that Aasif’s coming on board after 9/11 and Iraq wasn’t coincidental. You are looking to mirror the issues that are at the core of the days’ news. We started to realize that we didn’t really have an ability to make fun of the Obama campaign, in the same way as me going to meet soldiers gave the show a greater ability to talk about the war. If your world does not include enough access to different people, and their world does not include enough access to you, you are speaking from ignorance. We didn’t want to do that, and realized that we had been. So that was the impetus in hiring Wyatt. It was part of a process we weren’t that good at—diversifying staff, changing patterns, finding new tributaries. The general thrust of the show was just trying to get it done every day, and the reforming of more macro processes took longer than it should have. That’s me. I’ll take the blame.
But even within that, I didn’t realize the pressure it put on Wyatt. So even as we were growing and becoming more diverse, there were still blind spots.
Cenac came on as both a writer and a performer. Within days after arriving he had boarded a plane to Florida, where he bought a group of Jewish retirees the early bird special to explore whether race had anything to do with their opinions of Obama.
I had pitched this to Jon, and it came from a very personal place because I’m Jewish and my grandparents live in Florida. It wasn’t a story that I read somewhere. It was just like, I have a gut feeling that this is an issue: Obama is great, but I don’t think he’s going to get the old Jewish folks. And my grandfather’s one of those guys who’s not racist by any means, but just an old-school guy. I don’t know if he has it in him to vote for a black guy.
So we got all these old Jews together, my grandma’s friends, at the 3 G’s Deli in Delray Beach. We offered them a free dinner. It was Wyatt’s first field piece, and he didn’t have to do much at all. He pretty much just sat at the table and let the Jews fight each other for a couple of hours on camera. We called the segment “Baruch Obama.”
Wyatt Cenac: [seated at center of table, behind enormous corned beef sandwich] I was sent down to talk about this election and see what we could do to bridge the gap between Jews and blacks—
Art: I didn’t know we had a problem between Jews and blacks!
Silvia: A lot of Jewish white people here will not vote for a black man.
Evelyn: Wyatt, I want to tell you something. All of a sudden there is Barack Hussein Obama—
Al: His first name is Barack! It’s a Hebrew name!
Evelyn: Hussein is a Hebrew name?
Art: What is it relevant whether Obama’s middle name is Hussein or Yankel? I couldn’t care less!
Race and religion would prove to be rich veins of material during the 2008 campaign, with deft segments on everything from Reverend Jeremiah Wright to “terrorist fist jabs.” The Daily Show was underequipped to tackle gender issues, however, even with Samantha Bee doing brilliant and prodigious work. New contributor Kristen Schaal, who made her debut in March 2008, came out of the New York–Los Angeles alternative comedy scene that prized off-kilter storytelling as much as punch lines, and her spacy delivery disguised an acute intelligence.
I’d auditioned twice to be a correspondent, but didn’t make it past submitting a videotape. Then in 2008 I did a standup piece at this really cool show called Moonwork, on the Lower East Side. It was about Hillary Clinton running for the Democratic nomination, and she was steadily losing against Obama, and I was getting very frustrated because I was just so excited that she might win, and I felt if Hillary didn’t win just the way things were going in our world, we probably wouldn’t get another female president for, like, two hundred years. And Rich Blomquist, who I’d started dating, was writing for The Daily Show. Rich pitched it to Jon, who really liked it, and that became my first chat. I sort of did sleep my way in.
McCain, still irritated by his Iraq War argument with Stewart, made one appearance as a guest during the Republican primaries. But he turned down invitations after that, so The Daily Show came up with an ornery felt stand-in senator.
I would’ve certainly gone back on his show after 2008. But the McCain puppet they created—that was so great.
Yeah, the puppet. I thought it was hysterical. It’s the kind of joke that we enjoy. The puppet looked like John, too. They were making jokes about him, but in some ways you take it as flattery, that they would go to the trouble of making a McCain puppet.
But the time the show used a video of me to criticize John over his opposition to gays in the military? It was not fair and it was very uncomfortable, but that’s also the nature of the beast. We’re in public life, and so that comes with it, I guess. Of course I didn’t like some of the things that Jon Stewart said, but Jon Stewart is very talented. I don’t have to agree with everybody, but you know I enjoy him. Occasionally, yes, I’d like to throw my shoe at the television.
The 2008 campaign occupied much of The Daily Show’s attention, but Stewart didn’t forget about the guy who was still in the White House. The show kept up its (ultimately unsuccessful) eight-year quest to persuade Bush himself to appear as a guest. In the meantime Stewart grilled several of the president’s top advisors—and unveiled a furry red creature as a clever way to address one of the war on terror’s most troubling excesses.
The Bush presidency had been a great thing for us in terms of building our brand awareness. Yeah. Honestly, if Al Gore had been elected president, who knows what our show would’ve done.
His final year in office, one character I came up with that I was very proud of is Gitmo. That was me. I just thought it sounded funny. Just the word “Gitmo.” The word “Gitmo” sounds like “Elmo.” That’s all that it was. So I said, “We’ll just have a character called Gitmo.” It was just a pun. It’s ridiculous. Everyone loves puns. Some people don’t like the hacky puns. Some people like antipuns. But they’re still puns.
Sesame Street gave us a puppet for that.
They did not. He doesn’t know what he’s talking about. I made the puppet. I love D.J., but he didn’t deal with making any of that stuff happen, which is hilarious. He’d just tell me, “We want this,” and I’d be like, “Okay,” and it shows up. We bought an Elmo at Toys“R”Us or something, we bought a beard, and we put a beard on it. If I didn’t glue it myself, then Elise or Justin did it. We were a ragtag bunch. Jon would always say, “Don’t make it look too good.” I’m like, “Don’t worry. We can’t.”
The junior high arts-and-crafts-class look of the prop served a larger purpose, too: Gitmo was a device that allowed The Daily Show to express its agitation about torture without coming off as too strident.
Jon Stewart: [at anchor desk, with graphic reading GUANTANAMO BAYWATCH over his right shoulder] Last week the Supreme Court ruled on a motion to let war on terror detainees held at Guantánamo Bay contest their imprisonment before a judge. It was a complicated ruling. Nuanced issues. I’m gonna hand this off to Fox & Friends.
Steve Doocy: [in video clip, sitting on the Fox & Friends couch] “So with the recent Supreme Court decision saying that the detainees down at Gitmo can wind up with habeas corpus, where they get legal rights and stuff like that—”
Jon Stewart: [with off-the-shoulder graphic of important-looking musty book] Legal rights and stuff. It’s actually all been explained in Thomas Paine’s famous, “A Treatise on the Rights of Man and Shit.”
So how is this decision playing among those most affected? For that we go live to Guantánamo Bay, Cuba, and our Senior Imprisoned Correspondent, Gitmo. [split screen of tiny prison cell and red furry Muppet with bushy black beard]
You were just a cabdriver in Karachi when you were falsely accused by a reformer looking for reward money.
Gitmo: [in squeaky voice and vaguely Arabic accent] Yes. Snuff Al-Upagus will pay for this. He is brought to you by the letter bullshit!
Jon Stewart: Listen, Gitmo, wouldn’t you want a chance to prove your innocence? Maybe go free?
Gitmo: Yes, yes. Gitmo go free. Gitmo go home, get back in taxi cab… fill it with C4, and drive it into east entrance of British embassy! [bursts into squeaky ululations]
Jon Stewart: Wait, Gitmo, you just said you weren’t a terrorist!
Gitmo: When they caught Gitmo, Gitmo wasn’t. But Gitmo is now!
Closing Guantánamo was one of the rare policy positions on which Obama and McCain agreed. Otherwise the general election matchup was full of policy contrasts and personal intrigue, pitting an iconoclastic Vietnam War hero against a charismatic young racial pioneer. So naturally The Daily Show did everything possible to puncture sentimentality.
In August we were at Obama’s acceptance speech at the DNC in Denver. Stu Miller and Oliver were doing a bit on the floor, and they got me to come with them.
Obama is speaking, and I’m pretty close to the front, crawling upon all fours down from the front to interview someone right near the podium. There’s this older guy there, and I put the microphone in his face and ask him something, and I remember he put his hand on my shoulder and said, “Son, a lot of us have been waiting a long time for this moment. Please don’t ruin it.” I kind of… my heart shattered into a thousand pieces, and I started crawling, in defeat, back up the aisle, and all I could see was Smills [Stu Miller] and Margolis just saying, “Go back there, talk to him!” I go, “No, no, I will not do it. You have to leave me with one shred of humanity here!”
I don’t think either of us, Oliver and me, had ever felt worse. But Stu Miller was like, “No, no! We’ve got to ask all these questions!”
It’s an important historical moment not just for the people there but for the entire country. Fine. But it was a solid joke! And that was the only time we were going to get it! Oliver and Margolis refused to shoot it because they had some decency or something.
None of that aired. But there was a segment on the convention floor where Oliver stands next to this great-looking woman. Maybe she was a delegate, I don’t know. And John says something about Obama’s speech being so moving and emotional. And then he leans over to kiss her. And she bolts. That was real.
All I remember after that is the cameraman saying, “What would you have done if she kissed you back?” I went, “That was never a problem. It was never going to happen. There was no world in which that was going to result in an uncomfortable, impromptu make-out session.” If she had, it wouldn’t have been in the piece. That’s useless. What you need is the rejection, the humiliation. You need to feel the drop.
He wanted to be rejected by her on camera for comedic effect. That to him is more of a sexual thrill. Getting a laugh is much more sexually thrilling to John Oliver than a kiss. I mean, he’s a sick, sick man.
There were moments at the conventions, where we would realize the impact that the show was having, especially in the 2008 convention, when we were in Denver. I’d never experienced anything like this before. We got chased. By fans, by Democrats, which is worse than being chased by cops.
That same week, I was walking around with Oliver and Riggle and Jones. I’m the smallest guy. So there was Congressman [John] Murtha—big guy, eight feet tall, hands like fucking the Hulk, a Vietnam vet.
Oliver tells me, “Go up to Congressman Murtha and say to him, ‘What does Congress hope to not accomplish in the following year?’” So I ran up to him, I stuck a microphone in his face and I said, “Congressman, can I ask you a question? What does Congress hope to not get accomplished in this upcoming year?” And he was pissed, like he was not even fucking playing. And I look around and Oliver, Riggle, and Jones are gone. They vaporized. I’m just standing there sweating. I thought Murtha was going to hit me.
The crazy thing about The Daily Show is that happens and your brain goes to two places: “Oh, shit, this is going to suck because this guy might fucking punch me right now.” Then the other part of your brain goes, “If he punches me that’s going to be awesome. I’m definitely getting on the show this week!”
Denver was the Democrats’ show. But the Republicans succeeded in stealing some attention by announcing McCain’s pick for vice president: Alaska governor Sarah Palin. The Daily Show would have plenty of fun with Palin’s malapropisms and mangled syntax. What set the show apart, however, was that most of its jabs were aimed at the cynicism of McCain’s choice, and at Palin’s utter unpreparedness—notes that were struck right from the first Daily Show segment on Palin, hours after she was unveiled.
Jon Stewart: [at DNC anchor desk] The pick was a surprise, not least for Palin herself, who was asked about the job just a month ago.
Sarah Palin: [in CNBC video clip] “As for that VP talk all the time, I tell ya, I still can’t answer that question until somebody answers for me—what is it exactly that the VP does every day?”
Jon Stewart: Oh, mostly you just sit around being prepared to become the most powerful person on earth.
Senior Female and Women’s Issues Correspondent Samantha Bee joins us now with more on this stunning development. Obviously I know how moved you were by Senator Hillary Clinton’s run for the presidency. How are you feeling now about this extraordinary moment?
Samantha Bee: [sitting across desk from Stewart] It’s amazing, Jon. And as a proud vagina-American myself, I can tell you, I’ll be voting for McCain in November.
Jon Stewart: That’s it? You just vote for whoever has a—
Samantha Bee: A fun pouch.
Jon Stewart: Uh, the uh—
Samantha Bee: Love pita.
Jon Stewart: Right. But in many ways, Governor Palin is the ideological opposite of Senator Clinton.
Samantha Bee: Yes, but she’s her gynecological twin. You see, the thing is, let me explain: They both have vaginas—
Jon Stewart: No, no, no, I understand. But Senator McCain is somebody who voted against equal pay for equal work—
Samantha Bee: [her hands tracing circles in front of her chest] Boobies!
Jon Stewart: I understand that. But both McCain and Palin believe Roe v. Wade should be overturned.
Samantha Bee: Ow, ow, ow, ow! Can you just stop overloading my lady brain? John McCain chose a woman who is almost completely unprepared for the job, and who disagrees with me on every core value I believe in. But I will be voting McCain in November, because he understands—women don’t vote with the big head. They vote with the little hood.
Four days later The Daily Show had shifted seven hundred miles east and north, to St. Paul, Minnesota, to catch the McCain and Palin act in person. The Republican convention was a clamorous event, from the crowd of protesters that engulfed The Daily Show’s production trailer to the lightning bolt that struck a correspondent’s love life to the ominous fatigue that was nagging a top producer.
At the 2008 Republican convention, there was this one layer of the arena that we didn’t have credentials for, and it’s the only layer you wanted to shoot on because that’s where all the top politicians and dignitaries were. So we found a back stairwell that we could get up, and sometimes we would hide our camera equipment with the catering equipment, because the caterers liked us. So, you’ve probably got a few hours until someone realizes you’re not supposed to be here, or there will be a complaint from someone who you’d spoken to.
One day we were getting chased by security, we were about to get forcibly removed by them. I couldn’t get arrested because I was on a visa, so I ran like a child who’d broken a window. Like a coward. Some military vets hid us in this room that they had to change in. One of them was this woman, Kate Norley.
It takes a special woman to go, “Look at this frail, out of breath, scared, pasty man…”
Later I e-mailed her to say thank you, and also because she gave me her credential for the next day so we could shoot up there. I guess she was attracted to trouble. I guess that’s the same instinct that drives you to join the army and go to war.
That’s a cute and romantic story. But we’d shot everything we needed, and I do remember distinctly making several trips to that floor with Oliver for not the clearest of reasons.
Then we spoke on the phone every day for months. Kate was working out of Walter Reed, in Washington, after doing tours in Iraq during the war as a medic. I didn’t see her again until the next year. We got married in 2011.
But I don’t recommend that as a dating technique. The RNC is the least romantic place on earth, that’s for sure. The night I met Kate was the night of Sarah Palin’s hockey-mom speech, and as a human being, I was at a pretty low ebb then.
No, Sarah Palin did not seem like a gift. I remember when we were at the convention and she first came onstage, she was extremely impressive. We were all like, “Wow! Great choice, McCain. This is going to be an interesting race.”
And the more she talked the worse she was, obviously, and the more her past came out. But every politician was a gift. Even if you were someone who Jon putatively agreed with politically—if you were Bill Clinton, you were a guy who got some intern to give him a blowjob. Everybody was worthy of making fun of.
In some ways, the ignorance was less troublesome than the hypocrisy. I thought Palin would be a terrible person to be vice president of the United States.
I didn’t see a lot of Jon’s show in 2008, during the campaign. I was a little busy. But I was informed about what he was doing.
Oh, there was no doubt whose side he was on. Jon is not a raging liberal, but he’s left of center, and a candidacy such as Barack Obama’s was extremely attractive—hope and change, and on the heels of an economic collapse as well.
Listen, the one thing I have not only accepted, but understood well, and appreciated, is that Barack Obama was a candidate that really galvanized people—galvanized, to a large degree, Jon’s base as well. So Jon was, I think, in tune with them.
One change in context that worked to The Daily Show’s advantage, if to the detriment of the citizenry, was the continuing convergence of cable and network news toward an info-opin-tainment muddle, with viewers choosing an ideological silo. The rise of the Internet only sped up that fragmentation. And it gave The Daily Show’s hypocrisy-highlighting agenda even more relevance and credibility.
People would ask us, “Do you feel any moral obligation?” And journalistically, absolutely not. We tried to be fair, and just, and all those things for creative reasons, because creatively it’s more challenging and more rewarding.
Creatively, it’s more fulfilling to write jokes that are based on reality and are not cheap points and are not an endless series of “Bush is stupid, Clinton’s horny” jokes. But it’s not because it was any obligation to do it. We were on Comedy Central! Fox News is on Fox News. We do a better job of comedy than Fox News does with news. We lived up to our network’s title better than Fox News does or CNN does.
That proficiency was on nearly nightly display when it came to dismantling Fox’s tactics, particularly when it came to the “fair and balanced” network’s efforts to prop up Palin. The Daily Show’s ability to find and match contradictory video clips was peaking.
At the 2008 Republican convention, our production offices were in some kind of music school in St. Paul. You’d sit with the writers late at night watching postconvention coverage, and we see Karl Rove talking about Sarah Palin’s executive experience.
The Republicans were trying to convince themselves that Sarah Palin was a viable candidate for vice president of the United States.
We realize they’re praising her for everything they’d criticized Obama for not being. And Jon would hang out, especially on the road at conventions, and he’d remember, “There’s also an O’Reilly clip that fits.” So we’d call back to the producers who were in New York to pull clips—“See what’s out there from Dick Morris.”
Yeah, and you’ve got an army of PAs and interns who are putting transcripts into a database, so they’re searching those and feeding us tape at the convention location.
So by the next day we’ve got a great piece that really happened organically.
Jon Stewart: [at anchor desk] The GOP’s vice presidential nominee is earning rave reviews from at least one analyst with a head like a lump of unbaked bread dough.
Karl Rove: [in Fox video clip] “She’s a populist, she’s an economic and a social conservative, she’s a reformer. She’s a former mayor of, I think, the second largest city in Alaska before she ran for governor.”
Jon Stewart: Karl Rove is impressed with her experience as mayor of a city with 9,000 people in it. I imagine he was equally impressed last month, when Tim Kaine, former mayor of Richmond, population 200,000, former lieutenant governor of Virginia, and now current Virginia governor, was on Barack Obama’s VP short list.
Karl Rove: [in Fox video clip from one month earlier] “He’s been a governor for three years. He was mayor of the 105th largest city in America. And again, with all due respect to Richmond, Virginia, it’s smaller than Chula Vista, California; Aurora, Colorado; Mesa or Gilbert, Arizona; North Las Vegas or Henderson, Nevada. So if he were to pick Governor Kaine, it would be an intensely political choice where he was saying, you know, ‘I’m not really concerned with, Is this person ready to be the president of the United States?’”
Jon Stewart: Wow! Karl Rove is bitterly divided on this experience issue. Well, at least everyone can agree on the even more sensitive issue of Palin’s pregnant teen daughter.
Bill O’Reilly: [on the Factor one day earlier] “Millions of American families are dealing with teenage pregnancy. And as long as society doesn’t have to support the mother, father, or baby, it is a personal issue. It is true that some Americans will judge Governor Palin and her family. For the sake of her and her family, we hope things calm down.”
Bill O’Reilly: [on the Factor from 2007] “On the pinhead front, sixteen-year-old Jamie Lynn Spears is pregnant. The sister of Britney says she is shocked. I bet. Here the blame falls primarily on the parents of the girl, who obviously have little control over her. Incredible pinhead.”
Jon Stewart: See, what happens with opinions on teen pregnancy is that they gestate over a period of months. You pinhead!
Stewart’s sympathies may have seemed clear to McCain and Fox. But he regularly found openings to skewer Obama (and to tease the Daily Show studio audience about its reverence for the Democratic nominee: “You know, you’re allowed to laugh at him”). Stewart poked fun at the treatment of Obama as not just a candidate but a messiah, and he eagerly pointed out the contradictions between the Democratic nominee’s lofty rhetoric and his grubby compromises, as when Obama discarded a pledge to publicly finance his campaign.
Jon Stewart: [at anchor desk] We’re joined by Senior Electoral Regulations Correspondent Wyatt Cenac. How does Obama justify changing his position?
Wyatt Cenac: Jon, Obama struggled with this decision. He weighed the pros and cons. Considered every outcome. The many ways it might affect the election. Really, Candy Crowley said it best.
Candy Crowley: [in CNN video clip] “If you raised more than a quarter billion dollars in the primary season, would you limit yourself to $85 million in the fall campaign? Duh!”
Wyatt Cenac: I think it’s pretty clear. Duh!
Jon Stewart: But is “duh” really the best argument to justify abandoning your principles?
Wyatt Cenac: He’s raised a quarter of a billion dollars! He can buy all new principles! And this time he can put rims and a dumbwaiter on them.
Jon Stewart: He’s on tape, Wyatt, promising his supporters that he’s for public financing!
Wyatt Cenac: Look, Jon, we all say things we don’t mean just before we get rich. “I like taking the subway.” “The bleacher seats are fine.” “I love you.” “It’s an honor working here, Mr. Stewart.”
Jon Stewart: Is that from the list?
Wyatt Cenac: [after long pause] I love you?
Jon Stewart: You cannot escape the fact that what Obama has done seems somewhat hypocritical.
Wyatt Cenac: Don’t think of this as a moral failure. Think of this as pragmatism we can believe in.
My last day at the show was at the end of the 2008 Republican convention. Why did I leave? I just didn’t want the country to have a black president. Sooo kidding!
I moved to LA to write for what they called the Office spin-off, which became Parks and Rec. I went in to ask Jon to be let out of my contract, and tell him why I wanted to leave. And he said, “This show was my dream. I don’t expect it to be anyone else’s. It was wonderful to have you here.” It was not passive-aggressive. It was very, very real, and absolutely lovely.
The confluence of a close, possibly-history-making election involving four riveting characters—Obama had picked Delaware senator Joe Biden as his running mate—lifted The Daily Show to new ratings heights. Critical praise was on the rise, too. “At a time when Fox, MSNBC and CNN routinely mix news and entertainment, larding their 24-hour schedules with bloviation fests and marathon coverage of sexual predators and dead celebrities, it’s been The Daily Show that has tenaciously tracked big, ‘super depressing’ issues like the cherry-picking of prewar intelligence, the politicization of the Department of Justice, and the efforts of the Bush White House to augment its executive power,” Michiko Kakutani wrote in the New York Times. “The Daily Show resonates not only because it is wickedly funny but also because its keen sense of the absurd is perfectly attuned to an era in which cognitive dissonance has become a national epidemic.”
The presidential campaign coverage ended on a fitting high note. For the first and only time, Stewart and Colbert did the hour-long live election night show—or, more formally, “Indecision 2008: America’s Choice Live Election Special (A.K.A. The Final Endgame Go Time Alpha Action Lift-Off Decide-icidal Hungry Man’s Extreme Raw Power Ultimate Voteslam Smackdown ’08 No Mercy: Judgement Day ’08)”—together from The Daily Show’s studio.
There were a lot of famous people in the audience. I came down before the show, and Robin Williams is sitting there just chatting people up very amiably. That was amazing.
Standing in the studio wings and hearing Jon announce that Barack Obama was the next president of the United States, in 2008… it was one of those incredible, sort of weird, surreal experiences of being on The Daily Show. This is a moment in time. Then going backstage and watching the rest of the show, from the monitor, standing next to Robin Williams and Billy Crystal. Robin Williams and Billy Crystal and I, we’re watching The Daily Show together, backstage, at The Daily Show.
The Colbert writers came over to watch the election results with us and brought this Crystal Head Vodka, some product Dan Aykroyd had been hawking, and so we were kind of getting drunk and enjoying the moment.
It was very emotional, when Jon announced that Obama had won. I think you’d have to have a heart of stone not to feel the significance of the moment. Thank God we had a script to do right away, because I can’t talk without revealing my feelings. Afterward we all went to the writers’ room and watched Obama’s Grant Park speech. People were crying all over the place.
Oh, man. It was one of the most exciting nights ever, I think, besides the birth of my kids. Think about this: When I was a kid you couldn’t even be a black quarterback. You couldn’t lead a football team, let alone lead the nation. That’s the world I grew up in, so I was almost reduced to tears. When Jon made the announcement we were all singing and everything and it was a moment that was beyond politics. It was just this moment that we knew something different had happened, and we did that bit on the show where I came out with the tape and started measuring Jon’s desk, and Jon said, “What are you doing?” and I said, “Whatever I want.”
I remember we all went out afterward. A big group of us, walking from bar to bar until about four in the morning just celebrating. It was amazing.
After the show that night in Jon’s office, Jon was watching with Tracey and my wife and I, watching Obama’s victory speech and it was a great moment.
Robin and Billy were there, but I remember mostly the faces of the crowd in Grant Park, and the disbelief and relief and joy and their feeling of shock. Chicago is a very segregated city still, and with the great migration from the South a lot of them are very close to the bad old days. For them to watch this happen, that’s the thing I’ll remember most. That and Lieb’s fluorescent pants.
Oh, there were plenty of drinks around. We hadn’t intended like, “I’m going to be in Jon’s office for the victory speech.” But when it came up, it felt like, “Oh, this is a great place to be when this is happening. Okay. The country’s finally turned a corner and good stuff can happen again.”