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David: Do you remember shooting that scene?

Seth: I do. Me and Jason and James really got along well on the show and we had a good dynamic and it was never our instinct to rush through things, I would say. I mean, we would make a fucking meal out of it if we can. I’d say one line all day if I could, but it was always really easy and it never seemed like a laborious process. It never seemed like it would take a long time to get somewhere. Everyone was collaborative. It always seemed clear how to do it, I think.

Judd: I remember watching that scene and thinking, Seth’s a movie star. I mean, it just was clear. Like this is the kind of guy I want to watch in a movie. In fact, if you look at Knocked Up, a lot of it is the same kind of comedic idea of something happening that’s unexpected and having to figure out if you’re man enough to handle it correctly.

David: When are girls going to figure out that the jocks become used car salesmen and the nerds become, you know, Judd Apatow and Bill Gates? Why aren’t they on to that by now?

Judd: You know, that’s—uh, maybe they are. Any high schoolers here getting laid? Any nerds getting a lot?

Seth: Have you seen Kelsey Grammer’s wife?

Judd: David Spade.

Seth: David Spade. Bill Maher, even. Come on.

David: The 40-Year-Old Virgin started as a skit, right, that Steve Carell did about a middle-aged guy who had never had sex?

Judd: Steve was really funny when we were shooting Anchorman—crazy funny, like we were all watching him every day going, What is going on with this guy? He’s just playing so over his head every day.

Seth: Oh, it was crazy.

Judd: And so I said, “Hey, if you ever have any idea of something you can star in, let’s do it.” And he came up to me and said, “You know, I did this sketch at Second City that I played around with and never finished. It was about a guy playing poker with his friends and they were all telling really dirty sex stories and slowly you realize that he’s a virgin and his stories make no sense.” And then he said—and you know his example was, “You know how like when you’re with a woman and you feel her breasts and it feels like bags of sand, and you know how like when you put your hand in a woman’s panties and there’s the baby powder?” I just clicked in and thought, That’s the greatest idea I’ve ever heard. I was afraid to direct a movie and had not really pursued it because I didn’t feel, I don’t know, I just didn’t feel like I would do a good job. But then I heard that idea and I said, “Unfortunately, I understand what that is.” It’s not like I was a virgin until I was forty but I certainly had very long spans in between sex. You know, I’d go a decade here and there. I understood the issue.

David: Did the two of you then sit down and co-write it, and work together in a room somewhere?

Judd: He would come to the office and we would just bang it out. Very quickly, we realized that it should be real and that the character should be quiet. Steve and I talked about it as almost a Buster Keaton–type character. That he would be quiet and then he could get mad but he wouldn’t be a wallflower. He would be a really normal person. And that came from going on the Internet and finding all these blogs from middle-aged virgins—they all seemed a little scared, like it just got by them.

David: But his whole personality is shaped around this thing—his consumer choices, his temperament, everything. Because he just can’t get past that one thing. So it’s one of the most incredible pictures about neurosis—

Judd: It’s something that I kind of understood. That’s what a lot of Freaks and Geeks was, too: terror of intimacy, the fear that people will think that you’re a freak. They’ll discover the thing that you’re afraid might be true. Seth was in my office when we got green-lit for 40-Year-Old Virgin and got very aggressive about being in it.

Seth: I saw my moment. Judd was very happy. He was on the phone. He was like, “We’re making it?” And I was like, “Put me in it.” I tried to ride the celebration wave. He’ll say yes to anything right now.

Judd: Well, in my head I’d always wanted Seth to be in it. I tried to get Seth to be the lead of Undeclared and Fox network said no.

Seth: They literally laughed.

Judd: And so I was just so afraid that, like, what if I want Seth to be the lead and they say no? I was just hoping I could get it approved without telling him and then he got aggressive in the meantime. But Seth was a giant inspiration on that movie. We couldn’t get Superbad made, and as a result, his theory of people want a really dirty movie, we put onto The 40-Year-Old Virgin. Seth was aggressive with Steve about being dirty.

Seth: Steve had his reservations, I would say, about it. He actually had me write up a version of the script that was rated PG-13 at one point and I did it just so he could see how lame it was. I think he was underestimating his own sweetness and how much that would come across. I always thought he’s so likable and so nice that you could have the most despicable language and activity in the world surrounding him but he’s like the, the anchor of niceness, so you can get away with any of that stuff.

Judd: We did a table read with all the actors and I was so nervous that the script wouldn’t be good enough to amuse Catherine Keener—

Seth: Yeah.

Judd: We worked really hard on Catherine Keener’s part because she’s scary. You know, you don’t want Catherine Keener mad at you. She literally had just finished a Daniel Day-Lewis movie and a Sean Penn movie and then she’s, like, with us idiots, you know? I don’t want her to notice that this was a career mistake for her. So then we did a table read and Catherine and Steve murdered and Seth and Romany [Malco] and Paul just ate it.

Seth: Ate shit.

Judd: Yeah, and then we went into rehearsal and played around and we started telling sex stories and talking about our relationships, and Paul was very funny, getting mad about women who broke his heart and playing the guy who couldn’t get over it. And Romany had the craziest sex stories. He was like, “I lost my virginity when I was eight.” And we were like, “What?” And he says that in front of Sharon Waxman from The New York Times. And I’m like, you know, “Let’s not print the ‘Romany lost his virginity when he was eight’ story, okay?” Of course, it was in The New York Times. I said, “Isn’t that like a molestation?” He said, “No, I was into it.”

David: How did Knocked Up originate?

Judd: I had a lot of ideas about pregnancy because every time my wife and I went through childbirth, terrible things would happen with the doctors and the nurses—people being mean and not showing up or me cursing someone out, or them cursing me out. And so I thought, I’ve got to write about this because it’s so awful that I must get something from it. I liked the idea of a rushed pregnancy or something that sped it up, because even when you plan it, it’s so terrifying the entire time. Anyway, Seth was talking to me at the time and he was pitching some science fiction movie ideas and I was trying to explain to him that “I don’t think anyone would make a hundred-million-dollar Seth Rogen movie at this point. But you could do something simple because you’re funny in 40-Year-Old Virgin when you’re just sitting there on the phone. You don’t need ghosts and goblins and fairies.” I said, “You could just get a girl pregnant and that would be enough for a whole movie because you with the gynecologist—” And I went, Wait a second, this might be worth writing. That’s how it began.