Sick in the Head: Conversations About Life and Comedy

by Apatow, Judd

  Judd: That is hilarious. And you were never a dirty comedian.

  Jimmy: I never was a dirty—no, I never was.

  Judd: But your show now, in a way, is like sitting around, singing songs at the piano, enjoying people. Is that how you see it? I mean, the idea of my crazy Jewish family sitting around, singing a song, is unfathomable.

  Jimmy: This was a weekly event. This would happen all the time, and everyone would get involved. My sister wasn’t as into performing as I was, but we would play “King Tut” and come downstairs in my mom’s dresses—the ones that looked kind of Egyptian—and we would dance and lip-sync “King Tut.”

  Judd: See, I did all that and no one cared and I was alone.

  Jimmy: (Laughs)

  Judd: It’s like we have the same story—if everyone ignored you and you just watched Love Connection alone in your room every day for seven years.

  Jimmy: I look back, I mean there are tapes of me doing Pee-wee Herman and impressions of people, Michael Jackson, Eddie Murphy—

  Judd: I remember meeting you when you first got to SNL, I remember seeing you there. And I remember you did an impression of Adam Sandler.

  Jimmy: That was my breakout episode. Ben Stiller was hosting.

  Judd: That’s right. It was the Stiller episode. That’s why I was there.

  Jimmy: It was a Halloween episode, Ben Stiller hosted, and I remember Ben said to Higgins, “Hey, this kid does a great Sandler.” They go, “Yeah, yeah, we’ve seen it, but Adam doesn’t have a movie coming out, so we’ll wait until something—” and Ben goes, “No, it doesn’t matter. You should have him do it.” So we wrote up celebrity Jeopardy, where I did Sandler and Ben did Tom Cruise and Daryl did Sean Connery. That same episode is when I played guitar and did guitar impressions with Colin Quinn on “Weekend Update.”

  Judd: Yeah. Wow.

  Jimmy: Usually, if they know that a bit is going to kill, they’ll put it at the end of “Update,” but they didn’t think I was going to work that well, so they put me in the middle—and I crushed. It was a good bit. I did impressions of Alanis Morissette and all this stuff and no one knew—I was brand-new. It was my third episode, I think.

  Judd: That’s the biggest moment, when you realize you’ve found something that will make you break out a little bit.

  Jimmy: And that was it. I was the impressions guy. It all started happening from that one episode.

  Judd: You try so hard to figure out what will make people notice you—

  Jimmy: I remember I called Adam before I did it, because I wanted to make sure I had his blessing. They called him and put him on the phone with me, and I was so nervous. I was like, “Hi, Adam.” He goes, “How ya doing, man? Let’s hear it.” I go, “Okay.” I go (making funny sounds), I go, “All right, I talked to my mother the other day and she said, “What is wrong with you? There’s something wrong with you….’ ” And I was doing this whole bit, and he goes, “All right, that’s good. That’s good. You gotta do it.” He was awesome.

  Judd: That’s because no one ever calls or shows any respect in that situation. I remember Dana Carvey did Shandling on Saturday Night Live. It was really mean, and not a great sketch—I think Carvey called Shandling up after and was like, “Oh, I’m so sorry,” and Shandling wasn’t thrilled about it. Garry just said, “You know what? We’re going to do a Larry Sanders episode about it.” And then they wrote an incredible Larry Sanders where Larry was mad when Dana Carvey guest-hosted—he did an impression of him and tore him apart.

  Jimmy: I remember that. It was a great one. Out of all the things I watched to get ready for this job, Larry Sanders was the ultimate—that’s the ultimate piece of advice I’d tell anyone to watch if you’re doing a talk show. It’s so real and so well done. That’s how a show gets made.

  Judd: It seems like effortless, the way you generate all this material.

  Jimmy: Well, I think you have to keep trying and keep swinging and get up to bat and try a different type of joke, because you don’t know which one is going to connect. We try a lot of stuff that doesn’t work, and you go, like, “Wow, that one did not work,” but we tried it. And that’s what you have to do. I remember—it was the first season of Late Night, and you were nice enough to come on the show and you go, “This is great, this is fun, but honestly, remember these years because you will not be doing this much pre-tapes and stuff down the road because you guys will burn out. There’s no way.” And I really took that to heart. Every time I’m like, “We don’t have time to do that,” I think, No, you know what, I’m going to make Judd Apatow proud and I’m going to stay late, I’m going to stay till two in the morning. I swear to God, I think about it all the time.

  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.

  JON STEWART

  (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 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 the
y 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.