Sick in the Head: Conversations About Life and Comedy (26 page)

Judd:
Because Letterman, there was a moment when he just stopped going to New Jersey and knocking on doors, doing bits.

Jimmy:
But that was the best part.

Judd:
It was. It was incredible. And I felt a deep sadness when I heard he was not going to do remote pieces anymore.

Jimmy:
He was the best at it.

Judd:
It must have been odd to go up against Letterman, since he’s the one that made us all want to be funny.

Jimmy:
Yeah, but it’s just the way it worked out.

Judd:
Do you ever interact with him?

Jimmy:
I don’t. You know, we started joking back and forth a while ago. He would say—he would try to tweet me. Almost like he didn’t understand Twitter. He’s like, “I’ll tweet Jimmy Fallon!”

Judd:
That’s funny.

Jimmy:
It was a funny bit. Then, I would try to teach him how to tweet through Twitter, and then I think CBS asked him to stop.

Judd:
(
Laughs
) He was sending too many people to your Twitter account.

Jimmy:
Yeah. They were like, just stop saying his name. I think they have a blanket rule, CBS isn’t allowed to talk about me or something. So silly.

Judd:
Everyone in late night right now is great. It’s a weird moment, as a fan of comedy and good things: You go,
What am I going to do, get up every morning and watch five hours of talk shows?

Jimmy:
You can’t do that. That’s a waste of your day. But the bummer for me is that I can’t watch anyone else now because I don’t want to take any of their bits. Being an impressionist, I imitate everybody, so if I watch Letterman every night, I would start doing him in my show, and if I watch Kimmel, I’d do his bits, you know. So I get nervous and I just can’t watch anyone.

Judd:
Is there a part of this job that still blows your mind? For me, watching your show, when you’re standing next to Bruce Springsteen singing a song and doing a bit, I think, there must be a feeling of nirvana in that moment that I can’t even imagine.

Jimmy:
But when it’s happening, you don’t feel it. The
idea
of it happening—it’s almost happening, it’s about to happen—that’s the excitement. Once it’s happening, you just don’t want to screw it up and embarrass him and I want to make sure he’s having a good time, so I’m really kind of nervous and just want to focus and do well.

Judd:
The one that made me laugh was when you were singing with Paul Simon, and I realized, oh, there’s no joke here. Jimmy just forced Paul Simon to sing a song with him.

Jimmy:
(
Laughs
) I will never do anything like that again. I did that once and I sang “With a Little Help from My Friends” with Ringo, and that was the last time I’ll ever sing.

Judd:
No, you have to keep doing it. It just made me laugh so hard. This is a fun moment in late night. I would watch
The Tonight Show
, I never felt I was like Johnny Carson, but it’s funny for me now to have almost all those late-night slots filled by people I’m friends with or know a little.

Jimmy:
Yeah, you know them, and you’re like, wait, what?

Judd:
You can’t imagine Carson being as excited about doing his show as you are and we are. Like I don’t think Carson ever thought,
Oh my God, I can’t believe Dean Martin was here tonight.

Jimmy:
(
Laughs
)

Judd:
Those shows were driven by such darkness. Carson was funny, but he also looked like there was so much more going on here, which we didn’t understand. And I guess Letterman is that way, too. We were fascinated to see how these guys would interact with people because, on some level, we thought they were miserable.

Jimmy:
Yeah, well, you could tell when Dave hated somebody or when Johnny hated somebody.

Judd:
I think that people are generally struggling, and a lot of people are having a hard time and are miserable. To watch someone who is genuinely enjoying themselves is an elixir, and it shocks people. I think they watch you and think,
I wish I was that fucking happy
, and they get a real—it gives them a break. I think we watch Letterman out of our angry side some of the time.

Jimmy:
That’s not my style, so I’m not good at that.

Judd:
It taps into the national neurosis in a way, where people are so happy to not be unhappy. You know, we all want to be around the piano, singing the song.

Jimmy:
I don’t know if you had this, but I always wanted to please everybody. I always wanted to make everyone proud of me and happy.

Judd:
Yeah, but what is different for me is that, when I go home, I feel shame at the need to make people happy in order to feel good. I don’t know how you are afterwards, but it doesn’t feel like you have the bad aftertaste.

Jimmy:
When it’s the TV show, I don’t really, no. But if I’m at a party or a wedding and I have to get up and do some bit that I think is funny—and
if it goes well—I just go like,
Why did you have to do that at the guy’s wedding? Can’t he just get married without you being the big star?

Judd:
How is the social part of this life for you, where you get to know all these people that you look up to?

Jimmy:
It’s odd, but you get used to it after a little while. I don’t know, all of this is fun and surreal, and it’s just been getting crazier and crazier.

Judd:
And now you have two kids.

Jimmy:
I do.

Judd:
You have two girls?

Jimmy:
Just like you. I’m like, I finally get it now. It’s like, this is why you’re doing what you’re doing. This is the future. And also, God, it’s so worth it. It’s just the greatest feeling in the world. The little arms, they hug you and it’s like, ugh, it’s a crusher and I’m a mush. I’m an Irish emotional mess.

Judd:
You understand how people get needy with their kids because you’re like, “You’re still going to talk to me when you leave, right?”

Jimmy:
Totally. It’s so embarrassing. And you always say, “Well, I won’t do that, I’ll be the cool parent.” But you can’t help it.

Judd:
You can’t and you just—that balance of how do I give them rules, which they want to fight me on, and guarantee they want me to be their best friend at the same time is impossible.

Jimmy:
You invented this human, so you’re like,
I made the best human I can make. This is my Sistine Chapel, and I should be able to appreciate this. Not someone else.

Judd:
And then there’s that weird moment—and everyone tells you about it your whole life and you think,
No, that will never happen to
me
—where, for a year or two, your kids tell you to fuck off.

Jimmy:
Yeah. It does happen. Right around twelve or thirteen is what everyone’s telling me.

Judd:
That little kid who’s just, like, “I want to show you the teddy bear I bought”—twelve years later they’re like, “Get the fuck out of my room!”

Jimmy:
“Get the fuck out.”

Judd:
I have the thing with my daughter where I hate any boy that comes by—like, in my bones, I hate any boy that is circling.

Jimmy:
Yes.

Judd:
But there’s one kid that is like a super-goofy, nerdy kid, who I realize,
Oh, that’s me. That’s exactly who I was in high school.
And I’ll say, “What about dating that guy?” And she’s like, “Oh, he’s such a nerd.” And I’m like, “You don’t understand him. He’s special. He’s going to fill out one day. He’ll show everybody.”

Jimmy:
(
Laughs
)

Judd:
I’m like, “How come you don’t want to date my doppelganger?”

Jimmy:
But she will date someone like you.

Judd:
That’s the scary part. I wish I had self-esteem so she would like a guy with self-esteem.

Jimmy:
I’m going to be so bummed out because my daughter is going to marry some feminine guy that laughs at himself too much. And I’m going to go,
That’s me. She did it.

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 shit.

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. Fucking 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 God.” 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 fucking 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 showbiz guys can crush anywhere, anytime. You realize that what we would consider the gauntlet of stand-up—the shitty clubs, the one-nighters in Jersey, the hotels in Rochester, all the shit 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 analogous 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 post–
Daily 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 hell 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 fuck 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 analysis. 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 cocksucker. 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.