PLAYBOY: As a kid you had daydreams about being on Saturday Night Live. Once you joined the cast, did the reality live up to the fantasy?
SAMBERG: Absolutely. I had daydreams about being on the show when I was eight years old, but it got really intense when I was in college and doing stand-up in L.A. I started having literal dreams while I was asleep. And it was very specific. I didn’t dream about doing the show and being in scenes and having my own characters. It was more about being friends with everybody in the cast and just hanging out backstage and being accepted by them.
PLAYBOY: Your shaggy hair is one of your most distinguishing features. Does your contract forbid you to cut it?
SAMBERG: I’ve heard that before. That’s a total rumor. My hair’s short now, isn’t it? And I haven’t heard a word from anybody about it. Nobody seems to notice, so I guess my hair is less important than everybody made it out to be. I think they’re all secretly relieved that it’s shorter now. The other day Seth Meyers and I were watching clips from our first years on the show together. Seth said, “Samberg, it looks like your hair was trying to eat your head.” I could not disagree with him.
PLAYBOY: You’re starring this summer in Celeste and Jesse Forever, a movie about the slow end of a relationship. Do you have a personal preference when it comes to breakups? Are you usually the dumper or the dumpee?
SAMBERG: I’ve had my share of both. Actually, I don’t feel I’ve ever dumped anyone. It’s never been, “You know what? I’ve decided I don’t like you.” It’s usually about the circumstances. I had a girlfriend in college, then I transferred because I wanted to go to film school, and the long distance made our relationship impossible. Things like that tend to happen to me. Not that I haven’t had some brutal breakups. One time I was dating somebody and she told me, “Hey, I thought I was going to be on location for a film shoot for the next six months and now it looks like I won’t be, so we should break up.” I was like, “Okeydokey. I can tell I was really important to you.”
PLAYBOY: In Celeste and Jesse Forever you have sex with Rashida Jones after trying to put together an Ikea dresser. What is it about Scandinavian furniture that makes people horny?
SAMBERG: Ikea’s directions don’t make any sense, and you get a tiny little ice pick to assemble it all. I’ve put together a few pieces in my time, and it feels as though you’re moving in a slow-motion nightmare. That’s sexy, right? Any time frustration builds up about anything, it leads to sex. Sex is the great frustration reliever.
PLAYBOY: Adam Sandler plays your father in the recent film That’s My Boy. What type of father would he make?
SAMBERG: He’s more of a godfather figure. Once you’re rolling with him, he just calls and tells you you’re doing stuff. I’m in an animated movie with him called Hotel Transylvania, and I literally found out about it by getting a phone call from him. He said [in an Adam Sandler voice], “We’re doing a movie about monsters, and you’re gonna be the guy.” And I said, “Okay, sure.” I remember when I first got the job at SNL, I was a few shows in, and he called me at the office. He was like, “Hey, buddy, I figured I should say hello since our names are so similar.”
PLAYBOY: You’ve kissed a lot of hosts on SNL, from Scarlett Johansson and Paul Rudd to Bryan Cranston and Jason Segel. Who was your favorite?
SAMBERG: I prefer not to do any kissing on the show unless it’s for a laugh. I feel like there was an era on SNL when it had kisses just to make the audience go “Woo-hoo!” And I always hated that. Scarlett was my favorite because it was funny and gross. It was that scene where I play Kuato, the head from Total Recall that’s coming out of Bill Hader’s stomach, and she’s the female Kuato in Maya Rudolph’s stomach. It wasn’t so much a kiss as licking each other’s tongues. It was a kiss the audience definitely didn’t want to see happen.
PLAYBOY: You were raised in Berkeley, California by parents you’ve described as hippies. Were they pot-smoking, bell-bottoms-wearing, long-haired peaceniks?
SAMBERG: No, not quite that far. They both had long hair and wore bell-bottoms, but my dad also wore leather pants, leather boots and a leather jacket. He wasn’t a touchy-feely hippie. He just thought, I’m going to grow my hair long because that’s what they don’t want me to do. He likes to brag that he came of age in a time when you could walk through the wrong part of town and they’d chase you and beat the shit out of you for having long hair. But he’s a dad, so who knows how much of it is self-aggrandizing and how much is true? It was tough to rebel against my parents because of their hippie past. They’re really chill. They let us listen to N.W.A in the car.
PLAYBOY: You have two older sisters. Were they kind to you, or were you mercilessly tormented?
SAMBERG: They tormented me but in girlie ways. They would dress me up. Until I was five or six, my sisters were still making me put on diapers. They’d put my hair in pigtails and carry me around and make me pretend to be a baby. And I never fought back. I looked up to them and wanted them to include me in stuff. But it wasn’t so bad. You can suffer worse humiliations at that age, right?
PLAYBOY: You were voted the class clown in your high school. Did that title come with bragging rights?
SAMBERG: Remember, I went to Berkeley High, and being voted the best at anything was not something you bragged about. I had a friend who was six-five, superbuff, the blond quarterback. We all made fun of him for being the quarterback. Berkeley is the inverse of the rest of America. We’d be like, “Oh great, you’re the quarterback. How cliché. We get it, you’re so handsome and talented.” Nobody got more ripped on than the quarterback at our high school.
PLAYBOY: As a film major at New York University you made some bizarre experimental films, such as the short Monkey vs. Robot, which eventually showed up on YouTube. Are there any more cinematic gems from your past?
SAMBERG: That are better than Monkey vs. Robot? I highly doubt it. That was our high-water mark. One of my favorites, and one of the dumbest films I ever made, was a fake Calvin Klein commercial for a cologne called Cock. It was shot in black and white, very whimsical, with lots of arty shots like a man looking off a balcony while the wind blows through his hair. At the end, a woman’s voice whispers the name of the cologne, “Cooooock.” [laughs] I made the ck of Cock bigger on the label so it looked like the Calvin Klein logo. My film professor at the time hated it.