Judd: So they’ll be smart and miserable.
Jeff: Well, they go hand in hand.
Judd: Yeah.
Jeff: Do you know any smart people who are just, like, chill? Really happy? No, seriously, do you know any smart people just, like, “Hey, weeeee!” You don’t, do you?
Judd: I don’t. I mean, I don’t think I’m smart. But I think I’m beginning to think I’m smart based on how miserable I am.
Jeff: That’s a good way to measure it, by the way.
Judd: Yeah.
Jeff: But I know you and I’m telling you: You’re smart. You’re really smart.
Judd: They say certain people aren’t good soldiers because if they’re in a foxhole all night—you know, if you’re creative and smart, you’re thinking about all the different ways someone is going to blow your head off. But if you’re not that smart, you’re just like chilling out. And I feel like that in life. I’m just in the foxhole all fucking day thinking about everything that’s going to go wrong in every possible way.
Jeff: And that’s why you’re prepared.
Judd: The preparation is not helpful at all, really.
Jeff: I’m equally miserable but—by the way, we’re having a conversation here. It’s kind of rude if you don’t look at me.
Judd: I know, but why do you need to look at me?
Jeff: Because I’m talking to you.
Judd: You know, when I was first dating my wife, she said to me one day when we were talking, she said, “Dude, what are you looking at?” And I said, “I’m looking at your mouth.” And she’s like, “Why are you looking at my mouth?” “Because you’re talking, and I want to know what you’re saying.” And she said, “You know, when you talk to people, you’re supposed to look them in the eye.” No one had ever said that to me before. I was twenty-eight years old and I thought—
Jeff: Did you really go through life up until twenty-eight—I mean, did your parents tell you when you were a kid that you were deaf?
Judd: Like, I mean with—
Jeff: Like, “Look at the lips, it’s very important.”
Judd: Right now, I am having to make an extra effort to not look at your mouth.
Jeff: That’s crazy.
Judd: It is crazy and it makes me wonder how I was parented. Where was my mom looking? Was she looking at my mouth? It makes me realize what my damage is, and why it’s hard to connect with people: because I’m a mouth looker.
Jeff: So you say mouth looker, and that makes sense, but I never heard of that before.
Judd: Someone told me you exercise now.
Jeff: I’ve been exercising for a while. I do Pilates, for Christ’s sake.
Judd: Really? Like you slowly lift your legs with pulleys, every morning?
Jeff: Not every morning, but often enough.
Judd: With an instructor?
Jeff: With an instructor. I do privates.
Judd: You do privates?
Jeff: That’s one of the luxuries I actually partake in. I have to have privates because the thought of me being in a Pilates class—that’s goofy.
Judd: There’s nothing about Pilates that won’t make one of your balls fall out of your pants.
Jeff: By the way, nothing. You have to prepare for that ahead of time. I’m a big boxer-brief guy. With boxer briefs, you get no ball fallout. And then, I try to avoid—
Judd: You do Pilates in boxers?
Jeff: Boxers?
Judd: Didn’t you say boxers?
Jeff: Yeah, but underneath my sweatpants. With sweatpants, my balls aren’t going to drop out.
Judd: I don’t like that flexibility. I need it compact.
Jeff: No, boxer briefs hold everything in. You know what boxer briefs are?
Judd: No. I thought it was brief or boxers. I didn’t think it was the same.
Jeff: Boxer briefs are like longer briefs—like, they come down to here. You never worn those?
Judd: I have like tighty whities.
Jeff: Is that what you wear?
Judd: I don’t need the extra shorts aspect of it that you seem to like.
Jeff: Do you really wear tighty whities?
Judd: What does this do for you?
Jeff: There’s a certain confidence—I would have to drop my pants right now to show you. But I would not look like an idiot, whereas you, my friend, you wear tighty whities and we would be laughing at you.
Judd: The idea with that is that you have a bigger dick than me.
Jeff: I would wager everything I own that our dicks are the same size.
Judd: Really?
Jeff: We got the classic, average Jew dick. I see my dick all the time; I know it’s not big. It’s very normal size. It’s not like a tiny festival. But I don’t wear the boxer briefs because I have an extraordinarily large dick or small. My penis has nothing to do with it. It’s just a nice—it’s a very comfortable loungewear.
Judd: Okay. I was listening to an interview with you recently, and there’s a long section where you’re talking about what a good guy you are. Now, is that because you are a good guy, or like you’re such a murderer that you just say that?
Jeff: One of my favorite comedians of all time is Jack Benny. But besides being my favorite comedian, he also had a reputation of being the biggest supporter of other comedians and the nicest amongst comedians, and I really want to be known as, if not the nicest, then one of the nicest comedians.
Judd: Are you a people pleaser?
Jeff: No, I could give a shit about that.
Judd: There was a letter that someone showed me once—Jack Benny used to write letters to this television producer—but what made me laugh is that they were kind of dirty. And you don’t think of guys like Jack Benny as dirty.
Jeff: Right.
Judd: He was talking about how he loved a lot of the shows that year, but his favorite one was called “My Mother the Cunt.”
Jeff: Jack Benny wrote that? Wow. Because he really was clean and adamant about being clean.
Judd: So he likes that kind of joke but he thinks it’s wrong to do the “My Mother the Cunt” joke to America—like we can’t handle it?
Jeff: They couldn’t have handled it back then.
Judd: I just mean they all had a different sense of humor that they didn’t share with the public, like Milton Berle taking his dick out and putting it in a hot dog bun. But then when these young comedians like Robert Klein started showing up, they were all like, Oh, this is out of line!
Jeff: Let me ask you a question. You’re busy. We don’t spend a lot of time together but I look at you as a friend. J. J. Abrams is the other person who you remind me of in this way. And that is, I call you, I email you, anything, and right away, you respond: “What’s going on? How are you doing?” It’s not like two weeks later. But I, even being one hundredth as successful as you, don’t get back to people ever. I just wonder how you pull off being a great dad, a great husband. You’re this successful producer. You make movies. You’re producing a TV show for HBO. I mean, how do you do that?
Judd: Does this also relate to the fact that you have to keep saying you’re a good guy? When in fact you’re like the asshole who never returns emails?
Jeff: By the way, isn’t it true that when you don’t return someone’s email, they think there’s something wrong? Whenever I do write people back, their response is always: “Oh, I thought you were mad at me!” What? If I’m mad at someone, I tell them. But how do you pull this off? I don’t know.