'Daily Show' Alums John Oliver, Larry Wilmore on Working With Jon Stewart: "If You Laugh During the Taping, You're Fired"

John Oliver

Stewart's ex-colleagues spill on working with the soon-to-be ex-host: "He's got a lot of game left."

A version of this story first appeared in the Aug. 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

Rob Corddry
Daily Show correspondent, 2002-06

"In 2006, I was on the subway and a stranger asked me what we were 'planning on doing to the vice president on Monday.' I thought Cheney must have had another heart attack and was ready to explain the difference between tragedy and comedy when he said, 'Cheney shot his friend in the face.' If there had been a batpole on the A train I would have hopped on and slid right into Monday morning, besuited and swinging.

"To say Jon wasn't giddy about it would be like saying the vice president didn't shoot his 78-year-old friend in the face with a 20-gauge shotgun. That night, I was promoted to Senior Vice Presidential Firearms Mishap Analyst (Colbert must have been out of town) and of all the dumb things I was lucky enough to do on that show during my five years there, those three minutes top my list of favorites. Not just because the jokes were so expertly written by Jon and the writers, but because there's no greater feeling than being "in on it" with Jon, barely holding back your own laughter as Jon fails to contain his.

"I think the show is as good as it is because Jon inspires those around him to try and be as good as he is. You don't want to whiff because he never does. And, in case the point was lost, I feel like it's important to once again point out, for the record, that former Vice President of the United States Dick Cheney shot his 78 year-old friend in the face. With a shotgun."

Larry Wilmore
Daily Show correspondent, 2006-14

"I basically auditioned for The Daily Show on the air. Colbert had left a year earlier. Rob Corddry and Ed Helms were leaving. I started a week or so after John Oliver and Aasif Mandvi so I knew the show wanted to do something different. I had a reputation as a writer-producer because I had produced The Bernie Mac Show and written for The Office. Jon knew me as a writer but never as a performer; we'd never crossed paths during our stand-up days. He took a leap of faith: This was my big return to performing. I was very nervous! My first rehearsal did not go well. You have Colbert and Helms in your head — the people who'd done it really well. But you have to be yourself. That was the challenge. So we did the first run, and I couldn't quite be myself. No one was really laughing. I'm thinking, 'Oh great, I'm going to bomb on my first segment.' The crew didn't even want to make eye contact with me, like when you don't want to name farm animals because you might have to eat them later.

"The first thing that happened was a rewrite, which Jon did before every show, going through it line by line. He said, 'Let's just put this more in our own words.' I was still very nervous. I was sitting there getting ready to do the bit — we were starting fresh from commercial — and he turned and put his hand on my arm: 'Hey man, just look at the camera and fucking give it to America.' It was exactly what I needed to hear. My first joke got a big laugh and my stand-up instincts kicked in. The segment killed and the Senior Black Correspondent concept caught on from there.

"There's extra pressure when you're working with Jon. It's infuriating because he's usually right. Even if you disagree with him, you go, 'I know this motherf—er is probably right, but I'm still going to argue my point anyway.' And then later you say, 'Yep, he was right. How did he know that?!' It's been nice to work with him in a different capacity on The Nightly Show. Once again, he had magic words for me: "Hey man, stop being a f—ing host — just be you." But Jon can be very tough, too. During our first couple of months, he really pushed me hard. He'd say, 'So, what did you think of that show?' And I knew that was a trap. I was like, 'Uhhh. I'm not going to answer this.' (Laughs.) I felt like a kid talking to the principal. I'm a grown-ass man, why I do I feel this way? 'Oh, you thought that was good, did you?' 'Yeah, I did think that was kinda good.' And then we'd have a conversation about why it wasn't good. It would be a difficult conversation because he's the one guy who's telling you the truth. He'd say, 'This is why it wasn't good. Let's talk about it, let's get into the dirty and comfortable.' And it was very important in those first couple of months to have those conversations. Of course, he's also the first to say, 'Man you're f—ing killing it.'"

Ed Helms
Daily Show correspondent, 2002-09

"I remember doing my second segment — I was still so green and so nervous. It had a desk wrap-up, which was when the correspondent comes out to say some closing comments — those were always a very exciting thing as a correspondent because we didn't get a whole lot of studio time. So to have my second piece have one was thrilling, and also extremely nerve-racking.

"The bit was that I had had a little mole removed from my nose during the segment, and we treated it as this big, heavy medical segment. Katie Couric's on-air colonoscopy was the inspiration for it. So for the studio wrap-up, I had this jar with a huge long sausage floating in it and the bit was that this was actually the mole underneath my skin. It was a really dumb bit, but I could not keep it together. I was laughing really hard during rehearsal and then I was terrified because I didn't want to laugh during the taping. I knew that not laughing is the No. 1 job of a big news correspondent. So at the end of the rehearsal, Jon looks me in the eye and goes, totally deadpan, 'If you laugh during the taping, you're fired.' My heart just dropped. He held my gaze for a minute, and then he burst out laughing and just took all of the tension out. By making a really strong joke that played on my biggest fears right in that moment, he knew how to make me relax and be comfortable. It was a smart, hilarious and ultimately very gracious move."

Olivia Munn
Daily Show correspondent, 2010-11

"One of my first days at work, Jon took me aside right after rehearsal and said, 'There is something very important that I need to teach you.' My heart dropped. What did I already mess up? Then he grabbed two plastic 16oz cups — and started to fill them with ice. 'I'm going to show you how to make the perfect iced coffee.' His secret? Nespresso and Lactaid. I didn't want to tell him that I don't drink coffee and that my body is well-equipped to handle dairy products."

John Oliver
Daily Show correspondent, 2006-13

"I was really worried about not living up to his expectations when I filled in for him [in the summer of 2013 when Stewart was making Rosewater] and that something would happen where people would look to him specifically to guide them through it. And it did happen. The worst day [while guest hosting] was the Trayvon Martin verdict. I felt that the audience was looking for Jon to help them feel better. And I felt his absence hard that day. I said to him beforehand, 'If something comes down, if something enrages me, it's unearned. My anger is unearned.' And he said, 'Now is when you earn it.' "

Doug Herzog
President of Viacom Entertainment Group

"I remember the first time I noticed him, in the very early 1990s. The person I credit for discovering Jon was Eileen Katz, a development exec at MTV at the time. She had developed a game show and we were testing the concept in a conference room at MTV's headquarters in New York. The show was terrible. But as part of the format we had three judges, and Jon was one of them. As we walked out the room I said, 'That wasn't very good, but that guy in the baseball hat was really funny.' Eileen said, 'That's Jon Stewart, the guy I've been telling you about.' I was immediately intrigued. I said, 'Well, we need to be in business with this guy.' Before too long, we had him on the air with a show called You Wrote It, You Watch It. It was a very complicated format where people would write in letters and then we'd bring their letters to life in all different comedy forms. Jon was the host. It was short-lived, but we were smitten with Jon. He was brilliantly funny and, to this day, there's nobody quicker than Jon.

"So we put him on the air. The ratings for The Jon Stewart Show on MTV were just OK, and it was going to be a very expensive venture to keep on the air 40-some-odd weeks of the year. We didn't really have the stomach for that then, so we thought, 'Eh, he'll do it eight weeks here and there.' Jon really wanted to get into the business of being on every night, and understandably so. And then Paramount, our sister company, stepped in and was very interested. [It became a syndicated late-night show.] It was just like, 'Well, this make sense.' [It was canceled due to poor ratings in June 1995.]

"When I was looking to replace Craig Kilborn on The Daily Show in 1999. I knew I wanted Jon, but my instinct was, 'He'd never do this.' He was being talked about as heir to David Letterman. [Stewart had signed a deal with Letterman's Worldwide Pants production company.] And there was even this thing floating around that if HBO continued The Larry Sanders Show, Jon might replace Garry Shandling. He had a lot of buzz. Also, Comedy Central was a different place then. We had South Park, we were in 50 million homes or so, but we were losing Craig Kilborn. Then I got a call from Jon's manager, Jimmy Miller, who said, 'I think he might be interested in The Daily Show.' We took him out to lunch and didn't have to talk him into it. He was really excited. After lunch we had the cab take us straight to the William Morris Agency, where his then-agent — now manager — James Dixon worked, to make an offer. We were like, 'We're doing this now.' We were not going to let him change his mind.

"Here's what I know about Jon: When he makes up his mind, his mind is made up. When he told us in November about wanting to leave, he asked us to sit on it because he wanted Stephen Colbert to exit without the shadow of his news, and wanted to launch The Nightly Show without the shadow of his news. Then he announced to the world and we watched the reaction. It really took your breath away. Is he leaving a little too early as far as I'm concerned? Absolutely. He's still got a lot of game left. It's like he's pulling a Sandy Koufax. But I respect Jon and I respect his decision, and for the 16-plus years that he did it, every night he gave it his all. He left nothing on the table.

"To this day, he's still a self-effacing, low-key guy. The work always came first, still does. He's up there with Walter Cronkite and Johnny Carson and David Letterman. One of the great privileges of my job is that every once in a while I'd get to call Jon Stewart and go, 'Hey man, what's going on?' And then we chat about whatever: the world, the show, his kids, the Mets, the Giants. I'll probably miss that more than anything."