ONE

PLAYBOY: You next movie, Funny People, is about a middle-aged and highly successful comic dying from a rare blood disorder who mentors a young up-and-coming comic played by Seth Rogen. Coincidentally, you’re a middle-aged and highly successful comedy writer and director who’s mentored a young up-and-coming comic named Seth Rogen. Are you trying to tell us something? Do you have a rare blood disorder?

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JUDD APATOW: No, luckilythat part of the movie was all from my imagination. I can say with full confidence that I’m not dying from a rare blood disorder. Most of my movies are both completely true and completely false. Sometimes things are based on moments that have happened in my life, and other times they’re not even close. I just try to capture the spirit of it. I always wanted to make a movie about the relationship between two comics. The problem was, I didn’t have a great story. Nobody wants to watch a two-hour movie about a hilarious older comic being kind to a young man. That’s just a terrible, terrible idea. But then it turned into a demented mentor movie, with a father-son aspect to it. I find that fascinating. Funny People is about what happens when you meet your hero and you find out that he’s fucking crazy, but he has the job that you’ve always wanted and think you deserve. You have to decide whether you’re willing to turn into him.

TWO

PLAYBOY: Funny People doesn’t make a comedy career sound very appealing. Your characters suffer through failed marriages, fractured relationships, the slow conviction that everything they’ve done is crap, and eventually dying young. Is that what success as a comedian means to you?

JUDD APATOW: There’s a fine line between what’s healthy about being a comedian and what’s really sick and demented about it. And usually both of those things are happening at exactly the same time. When I’m doing good work, there’s a part of me that feels like it’s a positive contribution to society. I’m making people laugh and helping them think about their lives in a positive and life-affirming way. But at the same time, there’s a sick, wounded part of me that’s looking for acceptance, and just wants to know that there’s somebody out there who likes me. I serve both gods simultaneously.

THREE

PLAYBOY: In what ways are making a comedy movie different from therapy?

JUDD APATOW: It’s different because you don’t have a therapist to interpret your babblings. Just before I started shooting Funny People, I stopped going to therapy. And now that I’m finished, I have this weird instinct to avoid going back. I don’t know if I want anybody clarifying my feelings right now. I think it’s my own responsibility to work through all the issues that the movie raised for me. In a weird way, it seems like talking about it with a therapist would be cheating.

FOUR

PLAYBOY: In your movies, men do a lot of crying. Are you a naturally weepy sort?

JUDD APATOW: Absolutely. I’m a big crier. My wife and I both cry at the drop of a hat. Leslie (Mann) cries at anything. Yesterday, I came home and my youngest daughter, who’s six, told me, “Mommy cried during Jumanji today.” So we’re proud criers. Sometimes when my wife and I are watching a movie, we’ll both start to cry at the same time and then we’ll slowly turn towards each other, to acknowledge that it got both of us. That’s great and funny when we’re both crying, but not so wonderful when I’m the only one in tears. For some reason, the end of Doubt made me bawl. But when I turned to look at my wife, she was just staring at me, horrified. I don’t know why, but I always think crying is hilarious, especially in men. Guys have a hard time tearing down their walls and revealing who they really are. So nothing is more entertaining for me, for both comedic and dramatic reasons, then seeing a man burst into tears. (Laughs uproariously.) It’s just always funny to me. Men work so hard never to reveal certain parts of themselves, and I love pushing them to a place where they can’t stop from letting it all out.

FIVE

PLAYBOY: Your movies are so popular that your last name has become a verb. “Judd it up” has become a familiar refrain on Hollywood movie sets. Is it humbling to realize that you’ve spawned your own comedy genre?

JUDD APATOW: I don’t think that I’m doing anything particularly different or original. I’m working in the same comedic language as guys like James Brooks and Hal Ashby and Garry Shandling and Barry Levinson. There’s nothing new about comedy movies about underdogs who make an enormous amount of mistakes and learn from those mistakes. That goes back to Buster Keaton. We’re just doing our generation’s version of Buster Keaton.

SIX

PLAYBOY: When you were growing up, you used to transcribe Saturday Night Live scenes. In hindsight, does that feel like time well spent, or do you wish your youth had been wasted on other things like, say, girls and drugs?

JUDD APATOW: I wish we’d had TiVo back then, because it would’ve saved me so much time. Back when I was watching Saturday Night Live for the first time, VCRs hadn’t been invented yet. So whenever it aired, I thought to myself, “If I don’t watch this now, I may never get to see it ever again for the rest of my life!” I would put a tape recorder right up next to the TV, and then I’d sit up all night and transcribe the skits that amused me the most. I don’t know why I did it. I guess the show was just something I enjoyed and I knew it was going to disappear and I wanted to hold onto it. I did the same thing with Twilight Zone episodes.

SEVEN

PLAYBOY: As a teenager, you interviewed dozens of your comedy idols for a high school radio station, including Garry Shandling and Jerry Seinfeld. Did you ever listen to any of them and think, “I’m a thousand times funnier than this idiot?”

JUDD APATOW: Not really. I always tried to interview people that I respected. Some were nicer than others. Some of them would only chat with me for a few minutes, and some would give me hours and hours of their time. And then they’d hand me the phone numbers of all their friends. “Here’s Rodney Dangerfield’s home number! Call him!” Some of them taught me lessons that proved to be invaluable. I interviewed Jerry Seinfeld and he said, “It takes seven years to find your voice as a stand-up comic.” So when I started doing stand-up, I took him literally. I thought it would take me exactly seven years. I wasn’t impatient about it and I didn’t think I was awesome after being on stage for just a few years. It gave me a patience that I wouldn’t have had otherwise.

EIGHT

PLAYBOY: You started your comedy career writing jokes for Roseanne Barr. Are your closets filled with unused gags about overweight housewives?

JUDD APATOW: Actually, yes. I have a lot of files of old jokes that were never used or rejected. I’m very proud of the fact that I wrote solid jokes for Roseanne when I was 20 years old. I used to sit around my apartment and try to think of jokes from Roseanne’s perspective. I wrote this whole bit about stretch marks, and it was all about how the only way to get rid of stretch marks is to gain weight. Y’know, put on an extra 30 pounds just to bang ’em out. At the time, I didn’t think I even really understood what a stretch mark was. Writing jokes for Roseanne was the first great job I ever had. I would go to her house and sit at her breakfast table and just try to come up with ideas all day.

NINE

PLAYBOY: When your first two TV shows were cancelled — Freaks & Geeks and Undeclared — you sent a very angry letter to the responsible TV executive, wondering how “you can fuck me in the ass when your penis is still in me from last time.” Has time healed all wounds, or is his penis still in you, figuratively speaking?

JUDD APATOW: There’s nothing more painful than being cancelled. When you work on a television show, it can take forever to think of the idea, and then to write the script, and find the cast, and find the crew, and just get the whole TV machine moving forward. If you love it enough, it can feel like something you could feasibly do for years and years. But then sometimes it just ends, out of nowhere, and everyone has to go home. And you grieve for it, because you bond with all of these people and you have dreams for what you’re trying to attempt. I tend to take cancellation particularly hard. I cry and I have back surgeries and I’m bitter for decades. I go so far as to attempt to make every single person who every acted in any show I’ve ever been involved in a feature film star just so I can prove that I was right about the TV show. Sometimes the actors will say to me, “Wow, you must really think I’m good.” No, I don’t think you’re good at all. I just have to prove to that goddamn TV executive that he made a mistake. It’s not a sign of my support; it’s a sign of how insane I am. I’m the most arrogant man on earth, and I always need to be right.

TEN

PLAYBOY: From Freaks & Geeks to Funny People, you and Seth Rogen have been collaborating for over a decade. At what point do you become common-law married?

JUDD APATOW: I don’t know if we should be married or if I should become his adopted grandfather. Seth has said he thinks of me as his creepy uncle. (Laughs.) I like that. When you have a creepy uncle, he kinda makes you laugh. You’re happy to see him at parties but you’re relieved that at the end of the night you don’t have to go back to his house.

ELEVEN

PLAYBOY: You and Adam Sandler, who co-stars in Funny People, were roommates during the early 90s. Was that an Odd Couple-type relationship?

JUDD APATOW: We had a good time together. It was a $900-a-month apartment deep in North Hollywood. I paid $425 and he paid $475 because he had a bathroom in his bedroom. I had to use the guest bathroom. Most days, we would sleep till noon or one o’clock, get up, eat, spend way too much time in a mall, eat in a fine restaurant like Red Lobster, do standup comedy sets at the Improv and then eat again at one-thirty in the morning, usually fettuccine alfredo, and then go back to sleep.

TWELVE

PLAYBOY: While you were roommates, Sandler purportedly demanded to see your penis. Did he ever bother to explain why?

JUDD APATOW: He used to say, “I just want to know what I’m dealing with.” That was his only explanation. But I understood. On some deeply macho level, I understood. And then one day, I was peeing and he walked in the bathroom and caught a glimpse of it, and he just nodded his head. “All right, man. All right.” I guess I got his approval.

THIRTEEN

PLAYBOY: When we talked to Seth Rogen in March, he told us that you made some pretty bold claims about your penis. Apparently it has grey pubes and looks very distinguished and could teach a Harvard class in literature. Do you stand by that description?

JUDD APATOW: (Laughs.) That was just a joke I wrote for a standup act. It’s a complete fabrication. I used Grecian Formula now. It still looks distinguished. From a certain angle, it kinda looks like Ben Kingsley.

FOURTEEN

PLAYBOY: Many of your movies have featured male nudity. Why are penises so funny?

JUDD APATOW: Because a penis looks like a man with a big nose and large ears. (Laughs.) I don’t know if the penis itself is necessarily funny, but it’s the one thing that men are most proud of and most ashamed of at the same time. It’s a very vulnerable area, so it’s good for comedy. But you have to be careful about how much you show. I learned this from working on Forgetting Sarah Marshall, where Jason Segel was naked for an entire scene. When you show a movie with full frontal nudity to a test audience, you instantly learn how many seconds of screen time results in how many audience members walking out of the theater. You might get away with three seconds of penis exposure, but at five seconds you’re gonna lose eighteen people. And at ten seconds, it could be a hundred. The fear of the penis in modern society is unparalleled.

FIFTEEN

PLAYBOY: You know what sex comedies are missing today? Naked lady boobs. What happened to tits in comedy?

JUDD APATOW: That’s a good question. I can’t speak for other directors, but I’m the most prudish person when it comes to shooting those types of scenes. When we shot the speed-dating scene in The 40-Year-Old Virgin, where Steve (Carell) is talking to a woman and her bosom pops out of her shirt, I couldn’t have been more mortified. We did it in one take and I immediately wrapped the poor woman. But she couldn’t have cared less. She’d probably been stripping for 20 years for all I know. She couldn’t have been more comfortable with her nudity, but for me, it was like a hostile act. (Laughs.) It’s kinda funny, actually. I’m cool with a guy showing his dong, but boobs make me bashful.

SIXTEEN

PLAYBOY: If you take out the cursing and the male genitals, your movies have traditional, pro-family values. Do you consider yourself a closet conservative?

JUDD APATOW: I never think of my movies in those terms. I just try to tell stories that have some sort of positive idea behind them. Like in Knocked Up, I don’t think it’s a big leap to suggest it might be a good thing not to run away when you get somebody pregnant. I don’t think my values are so shocking. In my movies, there’s a lot of immature behavior, but it’s usually to point out how wrong it is, and to show that somebody is on a path to finding a better way.

SEVENTEEN

PLAYBOY: Abortion is dismissed in Knocked Up. In fact, the word isn’t even spoken. It’s described as “smushmortion”. Is it safe to assume that you’re pro-life, or anti-smushmortion?

JUDD APATOW: Well, if Katherine Heigl’s character had an abortion, the movie would’ve only been eleven minutes long. So that was never really an option for us. What interested me was making a movie about two people who didn’t know each other very well and decided that the right thing to do in their situation was get to know each other, just to see if a relationship could form. The baby was coming, and if nothing else, they could tell their child someday that at least they tried. That’s gotta mean a lot. Even if it didn’t work, he took the time to figure out if he really could be a dad. That was a more interesting premise to me than anything having to do with pro-life or pro-choice. An odd couple is forced into a relationship that turns out to be a great one.

EIGHTEEN

PLAYBOY: You showed some graphic details during the birth scene in Knocked Up, including the crowning. Why would you do that to us? Do you realize that because of you, most of us will never look at a vagina the same way again?

JUDD APATOW: I didn’t want it to feel like every other movie about giving birth. I wanted an audience to actually experience the birth, and I couldn’t think of a better way to do that than by actually showing it. That was in every draft of my script: “She gives birth. You see everything. This is not an episode of The Cosby Show.” I just wanted the audience to suffer through it.

NINETEEN

PLAYBOY: You brought along your nine-year-old daughter Maude to record the DVD commentary on Superbad. At this point, is it fair to say that your daughters are pretty much corrupted?

JUDD APATOW: I always say to my daughters, the reasons why people behave the way they do in my movies is because they’re idiots and everything is a what-not-to-do lesson. That being said, my kids haven’t seen any of my movies except You Don’t Mess With the Zohan and Heavyweights. Maude is eleven now and she’ll turn twelve later this year, and it’s getting harder and harder to not allow her to see my movies. It gets even more difficult because she’s been in several of them. I don’t know how much longer I can keep her away. But then again, I probably live in the fantasy land where I still believe she hasn’t snuck behind my back and watched them herself, at two in the morning on her computer. That may be why she’s not begging me to see them. If she was smart, she’d beg a little more just to make it look like she hasn’t seen them already.

TWENTY

PLAYBOY: In The 40-Year-Old Virgin, Steve Carell’s first experience with sex leads to an elaborate dance sequence featuring the song “Aquarius”. Is that similar to how you lost your virginity?

JUDD APATOW: Not really, no. When I lost my virginity, I said to the girl, “Hey, was it good for you too?” And she said, “Well, I guess it’ll get better eventually.” Sadly, she wasn’t right. It wasn’t better for her or any of the subsequent women who agreed to sleep with me.

TWENTY-ONE

PLAYBOY: In Anchorman, the Will Ferrell comedy that you produced, sex involves riding on unicorns to Pleasure Town. Do comedy directors have any idea how sex really works?

JUDD APATOW: (Laughs.) It would seem that we don’t. Well, I guess that tells you everything you need to know. Anchorman is about (director) Adam McKay and Will Ferrell’s fetish. They dig unicorns. And when I have sex, I’m always thinking about the Broadway show Hair.

TWENTY-TWO

PLAYBOY: When you became a contributor to McKay and Ferrell’s “Funny or Die” website, you promised to direct nothing but hardcore pornography. And yet thus far we’ve seen nothing. Where’s the porno, Judd?

JUDD APATOW: You know what? You got me. I have failed to come through. But there’s still time. At one point, I was planning to make a movie about a man dating a porn star. I interviewed a lot of adult actresses for research, and I had boxes and boxes of pornography in a storage unit. Shortly after I’d given up on the movie, I hired one of my relatives — a high school student — to help me out with some part-time work. On his first day, I asked him to clean out my storage unit, which I’d completely forgotten was filled with a massive stockpile of adult films. Well, I guess he stumbled across them and thought, “This may not be the job for me.” He didn’t come back to work the next morning. That was his first and last day.

TWENTY-THREE

PLAYBOY: We were going to ask you why so many of your films are about guys who sleep with hot woman way out of their league, but then we realized that you married a hot woman way out of your league, actress Leslie Mann. How’d you pull that off?

JUDD APATOW: I’m all about a multi-year plan. That’s how I approach meeting a woman. I’m not the kind of guy who just walks up to somebody in a bar and introduces himself. I’m the person who joins a club that they’re a part of and waits three months to say hello while sitting next to them. There’s a Freaks & Geeks episode where Sam Weir joins the high school yearbook just as an excuse to talk to a cheerleader. That was always my move. “What SAT class is she taking? I’ll join that!”

TWENTY- FOUR

PLAYBOY: As Paul Rudd observed in Knocked Up, “Marriage is like a comedy with all the jokes removed.” Do you agree?

JUDD APATOW: I think marriage is nothing but joy and fulfillment. And I don’t just say that because there is a one in four million chance that my wife will buy this month’s Playboy Magazine. My problem isn’t being unhappy in marriage. My problem is the exact opposite. I behave like every day is our first date. I couldn’t be more thrilled and terrified that she’s with me, and it never changes. Every day, I cannot believe she’s here.

TWENTY-FIVE

PLAYBOY: Leslie Mann has appeared in all of your movies, and has a major role in Funny People. What’s it like to direct your own wife? Can you say anything other than “you did a great job, sweetie?”

JUDD APATOW: It’s great directing my wife because she’s an amazing, hilarious actress. When you watch her, it doesn’t look like acting at all. It looks like I hid the camera in a closet and I’m catching her in an unguarded moment. I also like directing her because it’s the only time I get to tell her what to do. I can tell her when to show up, I can tell her what time she gets to eat, I can tell her what to say, I can tell her when to leave. That’s why every man should study filmmaking at USC.

TWENTY-SIX

PLAYBOY: A lot of your characters say inappropriate things to mask their pain. Is it the same for you? Do you use comedy as a defense mechanism?

JUDD APATOW: I don’t know how anybody survives life without doing that. That’s just how I am, and I think it’s how most people are, too. No matter how bad or painful a moment might be, my first instinct is to think of a joke. Most of the time I don’t say it out loud. But within seconds of hearing something sad, I’ve come up with the most terrible and inappropriate thing to say. It’s just how my mind operates.

TWENTY-SEVEN

PLAYBOY: Has success mellowed you, or do you still have the fierce ambition of a young filmmaker with something to prove?

JUDD APATOW: It feels good to have been around for awhile, because nothing surprises me anymore. I know what it feels like to have your movie bomb. I know what it feels like to have your movie bomb even though you think it’s really, really good. I know what it’s like to have your movie bomb when you know it’s not very good. I know what it’s like to succeed with a movie you’re proud of. I know what it’s like to succeed with a movie that even you don’t think is very good. I’ve been through all of the permeations. After everything that’s happened to me, I feel like I can relax and take a deep breathe. But as I get older, I’ve realized that nothing has really changed. The second I finish a movie, I always want to occupy my head with a new problem, a new project. I’m endlessly fascinated with the challenge of trying to crack the code of a story or a movie. If I was truly mature, I probably wouldn’t feel the obsessive need to keep making more and more movies. I would just smell a leaf for a few years and be satisfied.

(This story originally appeared, in a slightly different form, in the July 2009 issue of Playboy magazine.)