Marc: And that was your first real TV job?
Judd: I wrote stand-up for a few comedians and when they did specials I would be a co-producer or something. I wrote with Roseanne, I wrote for Tom Arnold. Then I met Ben at an Elvis Costello concert and we both knew that HBO was looking for a show—a sketch show—and we thought of something in two weeks and sold it. People thought we had been friends forever, but we had known each other for fourteen days.
Marc: In Funny People, there was footage of you and Adam and Janeane Garofalo.
Judd: Yes, and Ben.
Marc: And you were all in—what year was that, ’89 or ’88?
Judd: That was ’89 or ’90. And in the footage in the beginning of the movie, you see Adam making a phony phone call, which I actually shot in our apartment back then, and Ben Stiller and Janeane Garofalo are there laughing, so you see them very briefly in the opening credits. At the time, Adam was so funny but had no outlet so he would make funny phone calls for hours and hours. I thought it was so hilarious, it didn’t make sense not to record it. I felt bad that they would disappear and never be heard again, so first I would audio-record them and then video-record them.
Marc: Do you have all that stuff, too?
Judd: I have all of it. When we were doing Funny People, I found hours of Adam Sandler making phone calls. He was always calling Jerry’s Deli and complaining about the roast beef and saying that it made him sick. And they would always be so nice and then he would be, you know, an old lady and he would negotiate getting a free sandwich. It was always like, “Could I get a free sandwich for my trouble?” And they would say okay. And he would say, “Well, I had turkey but I don’t want to get hurt again, this time could I get the roast beef?” He would keep them on the line for twenty minutes, negotiating a sandwich. As a comedy nerd, I knew: That’s the guy. Adam’s going to hit. There’s no way this doesn’t happen. He just delighted us. He made us laugh so hard.
Marc: You keep using that term, comedy nerd, but back then it didn’t exist. You were just a guy who loved comedy.
Judd: I remember moving to L.A., and I started doing stand-up at this place called the L.A. Cabaret in the Valley, in Encino. And I started meeting comedians for the first time, personally, not just interviewing them. And I realized, They’re all like me. They all like the same stuff. I finally can talk to people about Monty Python and the Marx Brothers.
Marc: This is a recurring theme with you. These socially awkward, alienated guys that have to group with each other and sort of have this different type of strength to get through things.
Judd: Cocky nerds. My wife and I always talk about it. It’s people who think they don’t think ill of themselves—they actually think that there’s something special about themselves but no one’s noticed it. And so the characters on Freaks and Geeks—the geeks look down on the people who beat on them, but they still are terrified of them. And that’s what makes them interesting. They have an air of superiority as they’re getting pummeled.
Marc: You and Ben Stiller really created this community of comedy nerds in some ways. Do you feel that?
Judd: I think that Ben in a lot of ways is the beginning of much of what’s happened in modern comedy. He did The Ben Stiller Show on MTV with Jeff Kahn, which was a Larry Sanders–esque show, where it was behind the scenes of a sketch show where Ben played kind of a jerk. And I met Ben after he did that. So when we created The Ben Stiller Show [for Fox] together, I didn’t know what the hell I was doing. Ben knew how to make short films. I was just the guy trying to figure out how to not have Ben realize I didn’t know how to do anything but write stand-up jokes. So I’m just keeping my mouth shut and listening to Ben because he was already brilliant and had a vision for what this was, and slowly I figured out how to run a writing staff and edit, but I was faking it. I was faking it for a long time.
Marc: Isn’t that what everyone does for the first couple of jobs?
Judd: Yeah, but I was in charge of the writing and editing of the show. And so it was not like faking it as a staff writer. I was twenty-four or twenty-five years old with no background at all. And I hired people with Ben who were brilliant, like Dino Stamatopoulos and Bob Odenkirk and Brent Forrester and David Cross, and so in a lot of ways it was trying to manage these personalities who were bursting with energy. I mean, Bob was the funniest man in the world. The energy he had during The Ben Stiller Show—when he didn’t like someone else’s sketch, he would be like, “Oh my God, you can’t do that. Who wrote that? Your unfunny uncle?” I was so intimidated because I wasn’t anywhere near as strong as Bob but I also had to pick what sketches of Bob’s we would shoot on the show. And then David Cross came on for the last few and you felt like, Oh, this guy is in a whole other world with Bob.
Marc: Then you went on to do Larry Sanders, which is another defining show for comedy nerd-dom. I mean, that’s an amazing show.
Judd: That’s where I learned how to write stories. Garry was nice enough to hire me on that show after The Ben Stiller Show, but I had never written a story before.
Marc: You wrote sketches and jokes.
Judd: I knew how to write “Legends of Bruce Springsteen” but I didn’t know how to write about people. I was there, on and off, for five years and Garry ultimately allowed me to direct an episode and that’s how I started directing. But it was an amazing place to be. And also scary because it’s Rip Torn and Jeffrey Tambor and they’re brilliant and terrifying. Imagine having to walk up to Rip Torn and give him a note to change his performance. I mean…
Marc: How did that go?
Judd: It didn’t go well. It didn’t go well at all. I mean he, he was a blustery guy. But correct most of the time, and a wonderful person who would always wind up doing what you were trying to get him to do, but if you walked up to him and said, “Rip, I think you need to play it a little nervous here,” he’d say, “I’m not nervous! I’m in charge of the place!” “Okay, Rip, I’m sorry. We’ll just do it the way you want to do it.” Then, three takes later, he might give you one. And then he’d walk up to you: “Come on, did you like the one I did the way you wanted me to do it? That was all right.” I felt like I was watching some of the greatest actors of all time. Certainly some of the greatest comedic actors of all time. When they did the last scene of The Larry Sanders Show, where Jeffrey Tambor goes off on Rip and Larry and says, “There’s a book being written about Hank Kingsley and you are not in it, and you are not in it, and fuck you…” I forgot the exact words, but they did it in one take and wrapped the series. That’s ballsy. They were at the top of their game. It was fun to learn from them.
Marc: Do you think Garry is an underappreciated comic?
Judd: He’s the best. I mean, what he did with The Larry Sanders Show is an achievement that’s impossible to even explain. Imagine having to write a show. He’s the head writer. And then you have to rehearse it for three days and then shoot the entire show in two days. So seventeen pages a day while punching up next week’s script and editing two shows.
Marc: But also the idea that it’s not just the work ethic. All guys who do well work hard. But to create a cast of characters who work within show business that are pathologically selfish and narcissistic and not great people is, uh, difficult. It’s challenging to find heart there. And Garry clearly did—on that show, he did. You find heart through the weaknesses of all these extreme narcissists and lunatics. And I think that in some ways, in Funny People, that was your quest as well. It’s hard to sell show business as being a reasonable place for human beings to work.