Sick in the Head: Conversations About Life and Comedy

by Apatow, Judd

  Judd: You’re in a weird area. I would describe it as: Everyone thinks you are beautiful, but maybe you don’t agree with their opinion.

  Amy: Um.

  Judd: I’ll talk about me for a second. I always thought I was right in the middle, looks-wise, and that if I had a good personality, it could put me over the top. But it wasn’t like, behind my back, everyone thought I was handsome. I get the sense that you feel like some days you’re looking great, some days you’re not, but the audience sees you in a certain way that maybe you don’t agree with. Does that make sense?

  Amy: I think that’s probably true. I think that’s probably dead-on. I feel, like you just said, that some days I am like a real monster, completely unlovable and unfuckable, and then there’s a moment, every now and then, when I’m more like Elaine on Seinfeld: “Is it possible that I’m not as attractive as I had thought?” Or maybe it’s the opposite of that. Anytime I start feeling better about myself, physically, someone will say something that pushes me right back down. I think every woman feels this way.

  Judd: I ask about it because it is about who you think you’re speaking to.

  Amy: That’s a really good point.

  Judd: I was a year younger than everybody in school. I was the youngest kid in class, always. But I only realized, later in life, that I was much smaller than everybody.

  Amy: Physically?

  Judd: Yeah. And by the time I caught up a little bit, in sixth or seventh grade, I had been defined. On some level, I guess it made me feel less masculine. And as a result, I always feel like a nerd. I have a beautiful wife, I’m successful. But I still feel like the kid who’s picked last in gym class. And that shaped my idea of comedy being about outsiders. It was a way for me to attack all of these systems that I thought were unfair to me.

  Amy: I would say the same for me.

  Judd: What was your version of that? What happened to you as a kid that made you think and defined your sense of humor? Just the darkness of your house, primarily?

  Amy: Yeah, and one thing that’s too dark and private to even talk about. But I would say, with the physical stuff, that I was always pretty but not beautiful. And that was something that you were punished for. I was very aware of this stuff early on.

  Judd: With girls, it’s weird because it changes dramatically. In high school, girls don’t look anything like they looked in third grade. Whereas guys, the handsome third-grade dude is still handsome in high school. Girls blossom and change. That was the kind of girl I always tried to date: the girl who, near the end of high school, got pretty but still acted insecure.

  Amy: Well, that’s the jackpot. That’s my favorite kind of guy, too. The guy that blossoms but still sees himself as the fat kid.

  Judd: Al Roker.

  Amy: Al Roker is the perfect example.

  Judd: He lost the weight but he’s still nice to you.

  Amy: Because he remembers. But I had no perspective on myself physically. All I knew was that I was pretty enough to get by. I remember in fifth grade, a guy who I was friends with said something to me about being pretty. I got my period in fifth grade. I had, like, boobs. I had an ass.

  Judd: Well, that changes everything. That’s just pollution on Long Island.

  Amy: Only recently have I got any sort of ownership over my body as a woman.

  Judd: What does it feel like, going through puberty so early? Are you getting hormones, like a teenager?

  Amy: I was totally boy crazy, running around trying to kiss them. My parents were getting calls. But I wasn’t very sexual or anything. I remember growing pains, and my boobs hurt and I was just getting a body that no one else had yet. I remember being sexualized by gardeners—gardeners are the construction workers of Long Island, you know. I’d walk past a gardening truck and I remember feeling like, Wow, I’m way too young to be getting this kind of sexual energy from these guys. I only wanted that attention when I wanted it. I guess that’s what every woman wants. No one wants unwanted sexual attention. But I felt confused by it, and it’s why I talk about it onstage so much. It’s the confusion of trying to figure out how attractive I am and laughing at myself—I can be easily convinced that I’m gorgeous. Someone will be like, “You really are a beautiful girl.” And I’ll be like, “I know.” But then, an hour later, you’re in an environment where you feel like a troll.

  Judd: How does that relate to wanting to be funny?

  Amy: That was so interesting, when you asked me before about who I was talking to when I’m onstage. I just thought of that two nights ago. I was in Rochester and I was onstage and this is probably bad to admit, but I was like, I really am speaking to the women in the audience. I’m appreciative of the guys that can come along for the ride and not feel alienated because this isn’t some “pro-women, down with men” thing, but the reality is, I’m speaking to the women and trying to keep the guys interested enough that they still want to come to the shows.

  Judd: And what are you saying to them?

  Amy: “You’re doing the best you can and you’re good enough.” And that came from just sitting around with my girlfriends in high school and not having to pretend. You could just be like, “Well, I haven’t washed my hair in almost a full week, and do you want to hear what I ate last night?” You would feel so human—and, as a result, less apologetic.

  Judd: Your act is like that now.

  Amy: Well, I think it’s really comforting to people. It makes everyone feel better to acknowledge that no one has it together. I mean, I don’t know anyone that doesn’t have this big, dark cloud hovering over them. Just knowing that makes me feel better.

  Judd: At what age did you become aware of comedians?

  Amy: Really young, when we would watch the Muppets. And then I discovered stand-ups. I loved Gilda. I was so drawn to funny chicks. I remember watching Rita Rudner and George Carlin and Richard Pryor. My dad must’ve had it on. And Letterman.

  Judd: How old were you?

  Amy: Ten or younger. Stand-up trickled in over the years but it wasn’t until I was in college, early college, where I discovered Margaret Cho, and got really into it.

  Judd: At what point did you think, Stand-up is something I can do?

  Amy: After college. I was twenty-three.

  Judd: What did it take for you to think, Okay, I’m going to try this? Because it’s a crazy leap. The need to show up at an open mic—to even write your first joke. I was a lunatic about it. I was trying to write those jokes at twelve.

  Amy: How old were you when you got up for the first time?

  Judd: Seventeen. I had wanted to do it really badly since age fourteen, but I was afraid to admit it to anybody.

  Amy: My experience was like this: I was in an abusive improv troop after college. This guy set it up to get fifty bucks a month from each of us, but it was not really improv—it was a crazy, schizophrenic, delusional situation. I went one night to see one of the girls do stand-up at Gotham. It was like at six P.M. and she was bombing. Everyone was bombing. I thought, I want to try this because I’m not digging the improv but I like it when I say something and I get a laugh.

  Judd: That’s interesting. Because it’s not about being inspired by watching someone murder, it’s like, Oh, this is as bad as it gets. And I can do better.

  Amy: I still think that all the time. It’s not that I feel like what I’m doing is so amazing, but it’s pretty good compared to what other people are doing. So that same week, I was walking past the club and it was my birthday and I was like, I’m from New York, so I can get people in the seats. I had three hours to prepare.

  Judd: You wrote it in one day?

  Amy: I wrote it in two hours.

  Judd: How did you do?

  Amy: Pretty good.

  Judd: Do you remember any of it?

  Amy: I have a tape of it. I remember it. I talked about how skywriting annoys me. Don’t you find that when you talk about your early jokes, even though you know they were bad, you’re still trying to sell them? Like,
I still want you to think this is funny shit but I know it’s not. Anyway, I talked about skywriting, how it’s annoying and it fades and you can never read it. I was like, “If somebody proposed to me that way, I’d be like, ‘Fuck you.’ And so, like, this summer, do me a favor: Keep it at eye level,” or whatever. So horrible. But it went okay, I think. People came up to me and asked how long I’d been doing it, which suggested that maybe I could do this if I wanted.

  Judd: What were you doing for a living back then?

  Amy: Waiting tables at Michael Jordan’s Steakhouse.

  Judd: Trying to get acting work?

  Amy: Yeah, auditioning. But one day, this woman came into the restaurant and she really liked me. She was like, “I’m going to hook you up with my agent.” So I went in and I did a one-act play to audition for the agent and he was like, “You’re pretty mediocre and I have too many girls like you that are better than you.”

  Judd: That happened to me and I never acted again.

  Amy: Are you serious?

  Judd: Yes.

  Amy: Well, it made me furious. At some point, I started doing open mics. They were the worst shows in the world.

  Judd: So how long until you were okay at it?

  Amy: Four years. It wasn’t until the end of the Last Comic Standing tour that I was okay. I could do five minutes, but to do a twenty-minute set and have it be okay? That took three or four years.

  Judd: What was it like for you on Last Comic Standing?

  Amy: It was a reality show, so people were basically pulling for you. I was young, and I was excited, and I hadn’t been at all hardened by the business or anything. I was just so happy about it all: “This is great, guys, we’re telling jokes!”

  Judd: How far did you make it?

  Amy: Fourth place. And the other guys had all been doing it for twenty years, but I had an advantage in that way because I was funny off the cuff and on my feet. The competitions were good for the people with fresh minds rather than the hardened road dogs.

  Judd: And then you guys all toured the country and you hated everyone, right?

  Amy: Five of us toured and I died onstage every night. I would cry on the tour bus, and then go out and do it again the next night—sometimes two shows a night. We had this mandatory meet and greet after each show, so I’d have to stand out there and talk to everyone who had just not laughed at me.

  Judd: Did you get better over the course of the tour?

  Amy: My material was good, but I got better at selling it. By the end, I was pretty desensitized. I’d just been in so much pain every night that I stopped caring—and once that happened, it became more about my experience onstage. I was worried that I was going to offend someone because I’d be in Fayetteville, North Carolina, making a joke about how I think all gay people have AIDS, and then I’d look out and wonder, Is that okay? And the crowd was like, Well, we weren’t even going to question it, but now we see that you are. And then I would say something way, way worse right after that, so if they thought they were uncomfortable then…That became my thing, tricking people into laughing. Like, the real joke would be a subliminal thing that came after what you thought was the punch-line. It was comedy boot camp, and I feel like it gave me years of experience.

  Judd: Do you think you have a much different experience, as a woman on the road, than guys are having?

  Amy: Not in terms of the audience or anything, but in terms of fun? Yeah. Like, I’ve never hooked up with somebody after a show.

  Judd: I did.

  Amy: You did?

  Judd: Once.

  Amy: What happened?

  Judd: It lasted eight seconds and I looked in her eyes as she realized what a horrible mistake she had made. And then we had sex again and this time, it lasted six seconds and she really looked disappointed in herself for choosing to do this. If she became a nun after that, it wouldn’t have shocked me.

  Amy: Oh my God.

  Judd: And I thought, I’m never going to do this again. This is terrible.

  Amy: That’s why I’ve only dated two comics.

  Judd: It’s so boring on the road. If you’re on the road and you’re a guy and you’re bored, it’s almost like there’s nothing else to do.

  Amy: I’m just so lazy about what you do after. It just doesn’t seem worth it to me. The thought of leaving or having the guy leave afterwards, I’m just like, argh.

  Judd: Once I was playing the Dallas Improv and I hooked up with this woman after. This is how bad I was: She slept over and we didn’t have sex. I told a friend about it afterwards, who was a comedian, and he told me that every time he was with a girl, they would have sex. And I was like, “They go all the way with you every time?” I was like a thirteen-year-old.

  Amy: That’s amazing.

  Judd: She drove me to the airport in the morning.

  Amy: Oh my God.

  Judd: And her makeup was all smeared down her face. She looked crazy. And we had this weird goodbye, one of those things where you know you’re not going to ever call each other.

  Amy: Are we supposed to kiss goodbye like we’re a couple?

  Judd: And I thought, This is just heinous. I always tried to avoid all of that but every once in a while you would get so bored, you would think, I guess I should see what this is.

  Amy: And then you’re reminded that it’s vile.

  Judd: It’s never delightful.

  Amy: I’ve had one one-night stand in my life.

  Judd: And yet people see your act as very sexual.

  Amy: Right.

  Judd: So is that a character you’re playing?

  Amy: Well, it’s a part of me, too. Because the stuff you’re copping to and the saddest, worst moments of your life—that’s the stuff people connect to and appreciate. In reality, I’ve almost always had a boyfriend. But in those phases in between, I’ve never held out on sex at all. Like, I’ll sleep with a guy right away. That’s just what’s in my nature. If I want to, I’ll do it. I haven’t ever used that like as a trading or a bargaining chip but I am also thirty-three and single, so…

  Judd: You’re allowed to.

  Amy: Every year, if I have like one or two sexual experiences, they might both be hilarious.

  Judd: And then they add up, and people think, She must be doing this all the time. I have maybe six experiences from my whole life. But if I go onstage and tell three of them, it sounds like I have hundreds of them.

  Amy: Right. But you can get up there and do that, and you’re not the Sex Guy. But if I do it, I am. So I just embraced it.

  Judd: But those experiences are funny. That’s the thing. Your worst sexual experience can be so humiliating and hilarious, both in movies and in stand-up. They’re always the best stories. A guy who has got a lot of terrible sex stories is the best dinner companion of all time.

  Amy: It’s the best. I did one last season on my show, about the biggest penis I’ve ever encountered. It was like, that year I was single and I hadn’t been single for four years. I dated a wrestler and there was so much preposterous sex stuff from that relationship, and then I happened to go out with a guy and realized that his penis was way more than I bargained for. I probably already told you who the guy was, but he was an athlete. He was this guy my sister loved, a hockey player. I don’t watch sports but we winded up going out, mostly because my sister was like, “Oh my God, you have to go out with him! I’ve had a dream about you two falling in love!” So I go out with him mostly so she would think I was cool, but he was really hot and it was fun. I was like, There’s no way he’s going to be attracted to me. He could have sex with supermodels. So at the end of the night, I said, “I’m going to get out of here because I feel like a little insane with you.” And he was like, “No, I’ll go with you.” We went to another bar and then back to his place and—what happened with his penis, it was just so horrible and embarrassing.

  Judd: I haven’t heard that bit.

  Amy: You’re supposed to be really excited about a big penis, but when you’r
e faced with one, it’s like a unicorn—in theory, you’ve always wanted to see one up close but if it were ever standing in front of you, you’d be like, Fuck that, and you would run. You’d be like, Oh, it’s actually a horse with a weapon on its head. But in the moment, I was like, No, you have to do this. Everybody talks about how great it is. And I was like, okay, and I have a bunch of jokes in there about him going down on me because he was raised well but then I just realized that the guy has to do that, I mean he’s like lighting candles. This guy needs to get the girl relaxed. And then he kind of pulled it out and acted like it wasn’t a big deal. He was almost whistling like I wasn’t going to notice. And then I tried to get myself psyched: You can do this! You played volleyball in high school!

  Judd: You have to slow your heart rate down. Like a Buddhist monk.

  Amy: And then I say, “Do you have a condom?” He says no. And I was like, Way to call my bluff.

  Judd: They don’t make condoms that big.

  Amy: So then we tried and it didn’t work at all. It was not a possibility. I would have had to alter my body.

  Judd: He must be used to this, right? He must know it’s going to happen.

  Amy: At one point, I say to him: “Are you serious?” He’s like, “No, it’s usually—” And I’m like, whatever. In my twenties, I would have given it the old college try, but I’m in my thirties now and I was just like, I have Olive Garden leftovers in the fridge, see you later. It’s not happening. I’m not going to walk around New York with a gaping vagina because I had sex with you once.

  Judd: You tell that story and then you become known as a sex comic.

  Amy: It makes me feel like a little bit of a fraud, actually, and a little misunderstood. Onstage, I’ll talk about how I’ve never done anal, or no one’s ever cum in my face. I haven’t done anything out of the ordinary. I’ve been so boring. But people don’t hear that. All they hear is that you’re talking about sex.

  Judd: How does that affect what you decide to do on your show? There’s a certain amount of gender politics at play here, for sure, in what you decide to write about and talk about. Every sketch, in a way, ends up being about your position on certain things.