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Garry: Well, I didn’t know how to make it funny unless someone caught fire, and that certainly wasn’t an option. Nor was I equipped, as a younger man, to write the father-son emotionality that they were looking for at the end—so they had to help me. I remember I wrote three of those scripts in one season and then I went to the story editor Ted Bergman, who really helped me, and said, “How do you write fifteen more? Or seasons more?” And he looked at me and said, “Burnt out at twenty-six, huh?” When I told my therapist about this, he said, “No, you might be bored.” And it shocked me, because I never knew that that could be my own opinion. That’s when I turned to doing stand-up and looking at other types of television and what I could do that was different.

Judd: So your shrink made you the man you are today.

Garry: She really did help me. Because I didn’t think I had the right to be bored. You’re just so grateful to have this job. Who am I to be bored by writing for Welcome Back, Kotter and all these great shows?

Judd: That’s what we do: We instantly go to guilt and shame. I’m not allowed to have a feeling about this. I should just appreciate it and shut the fuck up. Right?

Garry: That’s totally right.

Judd: In all situations, I go straight to that feeling. Just shut up.

Garry: Who were your early mentors?

Judd: Well, my grandfather Bobby Shad was this guy who produced Sarah Vaughan and Lightnin’ Hopkins and Charlie Parker and Janis Joplin. He raised money when he was a kid—he was a poor kid—and would pay jazz musicians to let him record them and then he would make records and sell them in stores. Eventually, he started his own label, in the forties, and then—

Garry: You kind of saw the whole creative process right there.

Judd: Yeah, that’s what I thought. I remember feeling like, Oh, you can just do it. You can just start. But I had no musical abilities. I like music, but I just—I tried to play guitar as a kid and I couldn’t. What I liked was comedy. When I was a kid I said, “I want to know how they do it.” So I started this show for my high school radio station, interviewing comedians. I interviewed you, Garry, on the phone from Las Vegas and you had just hosted The Tonight Show for the first time—

Garry: It was the only interview I could get.

Judd: (Laughs) Here was this fifteen-year-old calling you on the phone, and you were very nice and funny. I asked you what your plans were for your career, and you basically laid out everything you would go on to do. You said, “I’d like to do a show, probably a sitcom, probably something personal, I’d like to play myself, I might play myself,” and this was in 1984.

Garry: That’s right. You remind me of two or three things. One, for some reason, is that so many of the comedians and comedy writers I know all pretended like they had radio shows, talking into their tape recorders or whatever when they were kids—it seems to be a common theme. I used to do that, too, but I never actually called anyone and interviewed them. You’ve always had bigger balls than most kids in comedy. The second thing is, I was a late bloomer. I was confused until I was twenty-seven and, as I said, started to get into that Roy London mentality. That’s when I realized I wanted to take the self-discovery path. I figured that would fit naturally into whatever project I felt was right, where I could continue to search this human condition thing we always talk about—because the human condition is hilariously awful.

Judd: I never thought about any of those things until I worked for you. I didn’t think in terms of the human story. You started thinking about it from Roy, and then I worked for you, and then you started talking to me about it, and—

Garry: Yeah, this is the big bang of it. By the way, my own belief is that I know how the big bang started—everyone’s confused—which is simply that shit happens.

Judd: Just random?

Garry: It may not be random, but “shit happens” is what we end up writing.

Judd: We’re getting into chaos theory right now.

Garry: When we were doing Larry Sanders, it was all about life and the question of self and what you were bringing to it.

Judd: You always used to say that Sanders was about people who love each other, but show business gets in the way.

Garry: And what people are always covering up—the tension between what they’re covering emotionally in life and what’s really going on inside them. What you really want to write is what they’re covering; otherwise you end up writing the exposition—which is just words. That’s what the struggle was in the writers’ room, in a nutshelclass="underline" getting people not to write just words.

Judd: I remember you said once that it’s very rare that anyone says what they actually feel, that we’re always trying to project on to other people, hiding our true motivations and feelings, and when you finally tell someone how you feel about something, it’s a big deal. As a kid, watching TV, I think I was learning all those things without even realizing it. I watched M*A*S*H, All in the Family, Taxi—you know, all the James L. Brooks shows—and those are all human comedies. I didn’t understand that what I liked about them was seeing normal people with their daily struggles, trying to be good people in spite of all of the obstacles that are in their way, trying to find connection. That’s what I enjoyed the most, but I didn’t understand how it was made and I didn’t understand how I would get there, until I worked with you at The Larry Sanders Show.

Garry: There’s a way I mentor that’s a bit on the Zen side, which is a little hard to understand because it happens in the writers’ room. Let’s just talk about you, Judd, okay? You, clearly, had youth and a point of view and energy and were really funny, and so what I wanted from you was whatever was pure that was coming out of you. The same pure thing will work for The Larry Sanders Show, or it will work for This Is 40—it’s just got to be pure. What I’m doing in the writers’ room is trying to sense whether that’s organic or not, trying to help people find themselves. That’s the lab we were in. And it turned out that we were filming it. Is that fair?

Judd: Yeah. I would notice things that were happening in your life, or things that you were thinking about, would make their way on the show. After The Larry Sanders Show, when I did Freaks and Geeks with Paul Feig, it was so personal to Paul. When we were making that show, I was always nervous about—what’s the tone of this show? And how can you do it really funny? And in my head I always thought, You know what this is? It’s a spinoff of The Larry Sanders Show. If we did Larry Sanders in high school, it would be this. That was always my secret thought.

Garry: Whenever you turn to what the organic state of any given character is, the fears and the anger and the struggle, you’re going to get conflict and a lot of hilarious stuff.

Judd: It also led me to realize that certain stories can be very small, but if you’re incredibly honest about them, there’s so much to do there. Take Knocked Up, for example. This is how we came up with that idea: Seth Rogen was pitching me a big science fiction movie, and I said, “Seth, you know, you could stand there and it would be interesting. In 40-Year-Old Virgin, you’re just in a stockroom and you’re interesting. You can do a whole movie where you get a girl pregnant and I would watch to see how that works.”