Sick In The Head: Conversations About Life And Comedy Part 22

(2014).

I've known Jon Stewart since we were both young comedians. After his first attempt at a talk show on MTV, he took some time off to write and act on The Larry Sanders Show, where I was working as a writer, and we spent a lot of time together. As great as he was on that show-his acting was fantastic and he was a force in the writers' room-I always felt like it was a rest stop on the way to something bigger. He was like a lion taking a nap before going out on the hunt. After Larry Sanders, of course, he went on to anchor The Daily Show-and, you know, change the way comedy and politics intersect forever.

There are certain people I've known for a long time that I feel an odd sense of pride in knowing, because I simply can't believe how brilliant their work is and what they've accomplished. It shocks me that I used to sit in the back of clubs with these people, and they went on to speak to presidents and influence people in such a profound way. Jon is one of those people. He makes me proud to be in the world of comedy.

Judd Apatow: I am going to ease my way into this with you, but how much stand-up are you doing these days?

Jon Stewart: You know, these past couple of years I have not done much, but before that, I was going out one weekend every month, every other month, something like that. I try to keep it to that.

Judd: And are you still writing new material for your act?

Jon: I keep it just stale enough so that the rote memorization I had of my act was still, you know, mindful to some extent.

Judd: I just started doing stand-up again about four months ago. I hadn't done it in twenty-two years.

Jon: Holy s.h.i.t.

Judd: But one of my strongest memories from my stand-up career was the night you and I were auditioning at Stand-Up New York for the HBO Young Comedians Special. And you went on and just smoked it. And got the special. And me, I had invited all of my high school friends to come watch, because I was still in my early twenties and still did things like that. Most of them had never seen me do stand-up, and I went up and ate it so hard. I still wake up in the middle of the night and get a shiver thinking about it.

Jon: How much do you love to bomb, though?

Judd: Uh.

Jon: Oh, I love the bomb. You have to embrace the bomb. And the bigger the moment, the tastier the bomb.

Judd: Is there one in particular that wakes you up in the middle of the night?

Jon: I think maybe the most pleasurable bomb was-you know, when you're bombing young and you're in the Cellar. Those are the most volatile bombs. Because you haven't quite established a baseline of confidence yet. So you really feel the sting of it. Like, I can't understand why those Dutch sailors don't find this amusing, you know. You don't realize the fragility of the atmosphere in the room.

Judd: Yeah.

Jon: I remember this one time. I had already been on TV for a bit by this time. They were reopening Radio City Music Hall, so this is probably the largest crowd I've played. It must have been five thousand people. And it's a big night of big stars-there's Billy Crystal, and they're raising him up on a platform through the stage floor, like he's Michael Jackson. He's leading the charge. f.u.c.king crushing it, destroying the room. Ann-Margret is in the audience. This is like some big return to glamour for Radio City Music Hall, and I come out and there is some confusion in the audience as to why I am there. I can feel it. Six minutes into the bit, and it had not in any way dissipated. What was impressive about it was, you would think the law of averages says that if you have a room full of five thousand people, some of them are going to laugh at some point at something, even if it's just something they whispered to their friend. You know what I mean? But it was total silence. Impressive in its discipline. At a certain point you think, like, Doesn't anyone here have a cold? Isn't anyone here going to sneeze? Shuffle their feet? No sound. I really felt like there was a moment of silence at some point for something; I just didn't realize what it was. I'm coming offstage and it was truly shocking, in its unanimity and uniformity. And I turn and look and there's Shirley Jones. She's backstage. I don't know Shirley Jones. She looks at me and doesn't say anything; she just opens her arms up to give me a hug. It was one of those, like, There, there, poor boy.

Judd: Wow. I had one where-well, I didn't perform but it felt like I had performed. I went to the AFI tribute to Mel Brooks, and I was supposed to get up and speak and I got really nervous.

Jon: You can't win that.

Judd: The place is packed and I'm with my daughter. I'm usually with my wife at these things, because she will encourage me and say, "Don't worry, you always do great." But my daughter is as scared as I am. She's sixteen and terrified for me. So I would say to her, "I'm really scared," and she'd be like, "Oh my G.o.d." And then the show starts. Martin Short does a medley of Mel Brooks songs. Tears down the house. Billy Crystal comes out with the most heartfelt, hilarious anecdotes. Tears down the house. Sarah Silverman comes out and does some variation of what I was going to try to do, only better. Decimates the place. I turn to my daughter and say, "I'm really scared. I don't know if I can do it." And she goes, "Don't do it. Don't do it." I walk over to the first AD and say, "I'm not going to speak." That was as bad as it gets.

Jon: You actually defused the bomb with, like, ten seconds to go. You f.u.c.king pulled the plug, man.

Judd: I totally pulled the plug, and then people just kept killing. The funny end of it is that special won the Emmy for best special and I thought, That's because I ran for my life.

Jon: You know what you did? You sacrificed yourself. To give them the Emmy.

Judd: I knew Mel didn't need me. He had enough love.

Jon: It's always stunning how the old-school s...o...b..z guys can crush anywhere, anytime. You realize that what we would consider the gauntlet of stand-up-the s.h.i.tty clubs, the one-nighters in Jersey, the hotels in Rochester, all the s.h.i.t you go through-is like a sanitized private school compared to what these guys did.

Judd: I asked about stand-up because it strikes me that you're basically doing a fifteen-to-twenty minute stand-up set every night on your show-and one that you've never done before.

Jon: The show is such a different animal, though. It's structured differently and written differently, and you have all the creature comforts of television to fall back on: The over-the-shoulder graphics, the montage, the willing audience. It's such a different experience. It doesn't feel a.n.a.logous to stand-up in any way, actually, and maybe that's why doing stand-up still feels pure to me. It's like when bands get a little more established but they still want to go back and play the clubs they grew up in. Stand-up is such a visceral, direct experience.

Judd: When you think about your postDaily Show days, do you hunger to be doing more live performance or- Jon: I hunger for a nap.

Judd: I know. I watch the show every night and I have the same reaction every night: How does Jon keep up this level of enthusiasm?

Jon: I always have this sense, with the show, that it is a beast that just wants to get the h.e.l.l away from us. And so the effort and energy that it takes to corral the beast every night-that is where your focus has to be. That being said, I guess I don't look at the forms as exclusionary. It's really a function of time, and I think that when I stop doing this, I will want to do stand-up. I just don't think I'll do it to the exclusion of other things, the way that we used to. The single-mindedness of it when we were younger is probably something I won't return to.

Judd: Here's the part that I am most impressed by: When I go to work in the morning, I'll usually have someone bring me breakfast. I get somebody to make me- Jon: Do you really?

Judd: Yeah, and I'll- Jon: What do you have for breakfast?

Judd: An egg white omelet of some sort.

Jon: Look at you, with the egg white omelet.

Judd: And that'll take me- Jon: Maybe a little spinach in there, a little tomato, a little feta?

Judd: I'll have a little-uh, yeah, spinach mainly.

Jon: Nice.

Judd: And I'll sit and I'll eat that omelet and I'll take an hour. I'll watch your show. I'll watch Colbert. Okay, so there's an hour where I've gotten no work done. And then I'll just kind of wander around and chat with everyone at the office and make a couple of calls. I can easily kill until one o'clock that way. But you have to hit the ground running. Hard. Every single day.

Jon: We work in an office. You know, it's funny. People always say to me, Ah, man, you guys-it probably must be so much fun, sitting around! And it's like, Yeah, our morning meeting starts at nine. We have to pitch out our ideas-and in some ways that is the challenge of a show. It's to create a factory that doesn't kill inspiration and imagination. You try to create a process that includes all the aspects of a mechanized process that we recognize as soul killing while not actually killing souls.

Judd: That is the invisible genius that the world will never understand. We worked at Larry Sanders Show together as writers, and we've had friends who have worked on many shows. And I find that, on most shows, the result of a very difficult process with high standards is that everybody hates the head guy. The head guy is not a beloved figure-whether it's Garry, Roseanne, or Cosby.

Jon: See, here's where I disagree. I think that's not necessary. When I was working on those other shows, I felt like there were aspects to it that didn't need to exist in order to maintain the creative excitement. It didn't need to be Machiavellian. You could get everybody to have common cause, and do it in a way that maintained a certain humanity. I always look at it like: Think of how much energy it takes to f.u.c.k with people. What if you try to use that energy to get the show done faster and better and get everybody out by seven? If I go into the morning meeting and I have clarity, and I can articulate that clarity, everybody's day is easier. If that doesn't happen, it's my fault.

Judd: How often does it happen that something heinous happens in the world, and you walk in and say, "I have no take on this whatsoever, it's so horrifying. I have nothing to say."

Jon: Well, then that's our take. And that's where the stand-up background comes in. What's the audience feeling right now? Let's just articulate back to the audience what they're feeling so at the very least, they get a recognition laugh as opposed to bringing them some sort of a.n.a.lysis. None of us may have a take, but if you maintain your ability to recognize a good idea, at the very least you know everybody is up for it. We'll sit in those meetings and we may come in with nothing, but at some point, it's sort of like it's a refinery. We've been here sixteen years, so we've sanded out every rough aspect of the process. Any extraneous energy that would be spent on things other than trying to make the show good have been removed.

Judd: I just always felt, and I don't know if this is your take on things, but when we did the last-season The Larry Sanders Show, life got very stressful.

Jon: It was tough.

Judd: It was tough for many reasons, but a big part of it was that the show was so personal to Garry. It was hard to crack what he would like, and he was acting so much that he needed the staff to come through for him so he could have time to sleep and do his work. There was a tension that couldn't be removed, which is: You were never going to nail it and it was always going to be painful for Garry because then Garry would have to say, "Okay, just come to my house on Sunday so I can rewrite the script." There was some pain to that. But as I've watched the evolution of The Daily Show, I thought that something about the experience of being at The Larry Sanders Show, and being around Garry, as complicated as it was, must have inspired you in some way.

Jon: No question. Well, first of all, Garry is brilliant. The biggest thing, and this is not necessarily what comes through on The Daily Show, but the biggest thing that I picked up from Garry was the difference between character and caricature. That idea of, you know, it would have been very easy for us to solve almost any story problem we had with Hank walking in and calling someone a c.o.c.ksucker. We knew that would kill, and it would move, but it would reduce everyone to two dimensions. Garry also taught me about intention. Intention is a really big thing at this show. We always want to know where's the intention and, now, let's find a path to that intention. Those were positive lessons. But then, there were the negative lessons, too-it's where I learned the importance of trying to create an atmosphere that was maybe slightly less volatile.

Judd: Yes, well, there was always that-the struggle that comes when certain people are trying to please their boss. My approach was always: This is an impossible job for Garry. I'm just going to try and help him in any way I can. But other people, when they would pitch a joke that didn't get through, would get angry at Garry. And that was destructive.

Jon: It's so important to remove preciousness and ownership. You have to invest everybody in the success of the show, and to let them feel good about their contribution to it without becoming the sole proprietor of a joke. There has to be an understanding that that may be a great joke, but it might not serve the larger intention, or the narrative, of the show. You have to make sure that everybody feels invested without feeling that type of ownership. The other side of it is doing twelve episodes is a very different process from having to set up something that can serve a hundred and sixty episodes, and I think you can get away with more volatility in that other environment.

Judd: And the storytelling requires that people go to some deep place, emotionally, which makes them vulnerable and raw. And on a show like Larry Sanders, you had the sense that the episodes are going to hang around for a long time, and be seen more over and over again, so you really can't bear to have a c.r.a.ppy one.

Jon: Correct. The fact that The Daily Show is ephemeral makes the process so much more forgiving. The idea that you're crafting twelve unique, careful episodes is very different than the feeling of, like, Okay, well, that one sucked, but who's on tomorrow? It gives you a cushion you might not have elsewhere.

Judd: Looking back, one could say that the final season of Larry Sanders is almost perfect, in its story line, with the young guy, played by you, pushing Garry out.

Jon: It's All About Eve.

Judd: And it is exactly what happened with Leno and Conan.

Jon: We created this template. People used to say to me, Larry Sanders is a satire on the dark underbelly of show business. And I always felt like, Oh, you have no idea. You have no idea of the darkness of the underbelly of show business.

Judd: How has the way that you look at The Daily Show changed over the years? Do you have a different sense of its purpose now?

Jon: I never think about its purpose. I think about its process, and that has changed dramatically. In other words, the evolution has been less about: What is our job here, or what is our purpose of being here? It's about: How can we make the show better, more distinct, with different voices? The two areas where I think the show has evolved the most are through the integration of new technologies, obviously-you know, search engines that didn't exist when we started, and that help us find material. When we got here, we used to cut the show in an online room. You could use maybe five rolls for an act and if you cut that montage and you got one of them wrong, you had to go back and start again. And I also think we have a better understanding of the diversity of voice. We've moved it from more of a strict, periodic structure into something that could become more essayistic.

Judd: Was there ever a moment when you realized, Oh s.h.i.t, people are actually paying attention to my point of view a lot more closely than I thought they would be?

Jon: There were two moments where that occurred, in some measure. One was winning an Emmy. That got in my head a little bit, feeling like I suddenly had a responsibility, that we had to live up to this thing even if I couldn't fully define what that thing was.

Judd: Sometimes I liken it to Chappelle in the sense that, for some reason, the responsibility of the show took him away from the idea of having fun, and enjoying himself.

Jon: The sense I got from Dave was it wasn't so much the responsibility as he wasn't sure if the show was being received in the way it was intended. I think Dave felt a responsibility, as a black performer, to live up to a responsibility and to not give people-you know, it's sort of what we call the bucket-of-blood laugh. George Carlin and I used to talk about that a little bit because he would do those shows where he'd be like, "You know, we only bomb brown people. We only bomb brown people except when we bombed Germany they were white people and that's because they were going, you know, because they were bombing people and that's our f.u.c.king job. That's our f.u.c.king job." It's a great bit but you definitely felt, in the audience, that there were some people going, "Yeah, that's our f.u.c.king job!" And for George, it created this sense of "Oh they're not taking this in the way that I intended it." And in some ways you have to let that go because it's something you can't control. You can only control the intention of the execution, but I think for Dave it became more complicated than that.

Judd: I get it, too, because every time I do stand-up, I wake up the next morning and I feel this shame that is so intense, like I was drunk all night and I don't remember what I did.

Jon: Really?

Judd: I feel embarra.s.sed at even having had an opinion or a thought.

Jon: But isn't that the whole-I mean, there's a certain arrogance in us entering this business. There's an arrogance in the idea of saying, Where's that spotlight shining? Oh, it's up on the stage? Well s.h.i.t, why don't I walk up there? What's in here that's going to amplify my voice? Is that a microphone? All right, so I got a light shining on me, and my voice is amplified and you're all looking at me. Well, let me stand here and give you something worthwhile for ten minutes. But I don't think it goes much further than that, if that makes sense. After that, it becomes a question of, does it resonate?

Judd: What effect does raising your kids have on the mechanics of getting all your work done and presenting your point of view with the world? How old are your kids now?

Jon: Ten and eight.

Judd: I have one about to turn seventeen and one about to turn twelve.

Jon: Oh dear, do they still like you?

Judd: They have to act like they like me because they still need me for some driving. But we're right at the end of that.

Jon: A little gas money might still keep you in the loop.

Judd: Maybe. But in some way, you must have perfected some sense of balance between your time at home and your time at work-which seems impossible, given how demanding your show is.

Jon: I have done my best, but it's still not satisfactory, especially as the kids get older. It's different when they begin to share and experience things that are more complex. It's one thing to, you know-I have this letter up in my office. It's something my daughter Maggie wrote to me. It says, and this was after we were down the Jersey Sh.o.r.e, bodysurfing. I think I tanked it and smashed into the sand. It says, "Daddy, I know you are a good writer. You're a good surfer, too. When you got on that big wave, you got hurt bad. I know you saw a lot of nature. You're a great dad. Love, Maggie." That is, like, beautiful. It's simple. But now, they're older and they are beginning to articulate things in a much more complex way, and you need to be there more. And nine-to-nine is a s.h.i.tty schedule for that kind of thing. So I'd like to say that I've achieved that balance, but the truth is, I probably haven't.

Judd: The conversation I get into in our house is: "Dad, we have money, so why don't you stop working so much?"

Jon: Because I'm an obsessive weirdo?

Judd: And what if Ebola happens in a much larger way and we really need to get the compound solidified?

Jon: Exactly. You are just preparing. I also think, to some extent, you are where you came from. No matter where you end up, no matter what you achieve, on some level, you feel like you belong in a bas.e.m.e.nt underneath a Middle Eastern restaurant telling jokes. That's never out of you. Leno used to have this. He'd always say, "I never spend any of my stand-up money." He'd been doing The Tonight Show for like twenty years, and he'd say, "I don't spend my stand-up money. That goes right to the bank because you don't want to mess with that. You never know what's going to happen." And you're like, "Yeah, I guess the collapse of Western society maybe, but I think you're in pretty good shape." It's a psychosis more than anything else.

Judd: I know that when I started doing stand-up again, and I would get eighty dollars for my Sat.u.r.day night spot at the Comedy Cellar, I held on to that money with a joy that I don't get when the Drillbit Taylor residuals come in.

Jon: Because we're psychotic and, at some level, not living with a real sense of things. But also, you know, I like working, man. I just wish I was better at it. One of the nice things about doing this show versus stand-up is that there is a moment of Zen at the end of it. There's a good night. You're done. With stand-up, you're never done. You always feel like you've got to keep that notebook by the bed. And so you stop experiencing anything. You just exist purely as an observer, constantly trying to figure out if I'm going to be able to work a bit out of this. It's a different way of approaching life. It's exhausting.

Judd: How is it that your family's not angry at you?

Jon: You'll have to talk to them. I think there's a certain normalcy. My kids have never known me not to have this schedule.

Judd: Do you enjoy work in the same way after all these years? Has the pleasure of it changed? Because what I find most shocking, as someone who burns out-I mean, we did thirteen episodes of The Ben Stiller Show and I literally prayed for cancellation in my room at night-I can't believe how vital and alive your show is, and with no sense of burnout.

Jon: It's hard. In some ways, I think it's cyclical. I liken it to batters in a slump. Sometimes you just have to simplify, return to basics. You know, All right, well, I'm not hitting right now. That's when I feel the worst, when I feel like I can't-the inspiration's just not there or you feel like you can't solve the problem with the joke. You can't elevate. That's when you feel the s.h.i.ttiest and so, in those moments, you just have to think like a baseball player: Okay, if I'm not hitting, at the very least I'm going to run out every ground ball as hard as I can. Or I'm going to do the best I can in the field. I'm going to try and make up for my lack of creativity until, hopefully, I hustle my way out of that slump. But I will say this: Through it all, I have always retained the ability to feel the joy of the funny. When somebody comes up with something really funny or we hit a jag where it's clicking, that still feels like that wave you've been chasing. It can still make me jump up and down like a little kid. That's what you chase.

KEY AND PEELE.

(2014).

Whenever I sit down with Key and Peele-which is fairly often, and we're usually talking about a screenplay we're working on together, and who knows if we'll ever finish it-I think: I wish I had a Key or a Peele in my life. The only two people I've seen who seem as close in their friendship and sensibility are Seth Rogen and Evan Goldberg. I mean, where's my Peele? Where's my Key? Why the h.e.l.l am I sitting alone in this room?

Anyway, these guys are hilarious and, maybe more important, they seem to be having the best time in their work, and with the fact that they get to do it together. They are funny and sharp on all subjects, but I can't think of anybody who has been better on the subject of race in America. They have found that magic formula of making people laugh until they s.h.i.t themselves while also saying things that need to be said right now.

Judd Apatow: So you've just finished shooting the show, and you did two seasons at once?

Keegan-Michael Key: Yeah, pretty much.

Judd: That's crazy. Was it a nightmare? Two-thirds of the way in, did you go, "This is a terrible decision," or did you not hit that level of suffering?

Key: Some things fell through the cracks. We'd be on set, trying to fix things, but then we'd have a hiatus week, and then we'd have to shoot something for Comedy Central on the hiatus week, but while that's happening there's always still a stream of emails that come through saying, "Here's the second version of this cut, of this episode," or, "Do you guys want to give notes on this?" And there's just no time to weigh in on all that stuff.