This story appears in the July/August 2012 issue of Playboy. Subscribe


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.


PLAYBOY: Why did he hate it?

SAMBERG: I had a few professors who gave me bad grades because the subject matter of my films was silly or stupid. They thought I was goofing off. If you weren’t doing dramatic narrative or message-based films—statements about youth or whatever—the professors thought you weren’t trying. But I would argue that it would take me just as many hours and just as much work to write, shoot and edit these things as it did anybody else. They saw it as not taking the class or them seriously, when in fact I was taking it seriously. It was the most focused I’d ever been in my life.


PLAYBOY: You became pals with Mark Zuckerberg, the Facebook CEO, after impersonating him on SNL.

SAMBERG: He’s a nice guy, and I like him a lot. I don’t know if my impression of him is all that good. If you look at us, we could basically be cousins. And we both have berg in our last names. I’ve played three guys with berg in their last name on SNL. There’s Zuckerberg, Jesse Eisenberg and Mark Wahlberg. Sooner or later I’m going to have to do Ryne Sandberg from the Chicago Cubs so I can say I’ve done all the bergs.


PLAYBOY: One of your first digital shorts for SNL, Lazy Sunday, became a huge hit on YouTube. Is the internet still the best source for original comedy?

SAMBERG: I think it is, yeah. Most of my inspiration comes from YouTube. The digital short SNL did with Jonah Hill getting hit in the nuts repeatedly with a tennis ball—that came from something we saw on YouTube. We jacked the whole thing. Also, I did a short called Seducing Women Through Chess, which was a complete rip-off of an amazing video I saw called How to Seduce Women Through Hypnosis. It’s one of the most unconvincing things I’ve ever seen in my life—poorly edited, poorly acted. It’s just fantastic.


PLAYBOY: In the digital shorts you’ve made over the years, you’ve somehow managed to convince Natalie Portman to rap about her sex life and Maroon 5’s Adam Levine to sing about having romantic feelings for an Iranian dictator. What’s the secret to coaxing celebrities to sing less-than-flattering lyrics?

SAMBERG: With Natalie it was easy. It was all her idea. She loves filthy rap. She’s a big Lil’ Kim fan. She saw Lazy Sunday, and when she came to host SNL, she said, “I really want to do one of those raps.” We were skeptical because we thought of her the same way everybody else did. She seems so sweet and innocent. But she was like, “No, you don’t understand.” And then she broke into some Lil’ Kim song and started rapping verses for us, the filthiest lines I’ve ever heard. We were completely taken aback.


PLAYBOY: One of your most popular SNL videos, Dick in a Box, made a convincing case for gift-wrapped genitals. As far as you know, has anybody ever tried that?

SAMBERG: I heard a guy got fired from his job for doing it to a female co-worker. People were asking me, “Do you feel responsible?” Absolutely not. If it wasn’t that, it was going to be something else with that guy. He was going to do something stupid eventually. The only thing I witnessed personally was one Halloween a guy in a bar came up to me, totally hammered, and was like, “Dude, check it oooooout!” He had a box attached to his waist, and there was a huge, realistic-looking dildo inside it. I said, “Hey, man, you probably shouldn’t show that to people.” He got all sad about it and was like, “Yeah, man, you’re probably right.” That’s the closest I’ve come to seeing an actual human penis inside a box, thank God.


PLAYBOY: You’ve done several music videos for SNL with Justin Timberlake, mostly as a pair of R&B-singing best friends. Is that fictional relationship analogous to your real relationship with Justin?

SAMBERG: I think the characters are better friends than Justin and I are. They’re about as close as two men can be, if you know what I mean. I consider Justin a friend, but those guys are inseparable. The funny thing is, Justin and I have become inextricably linked because of those videos. We’ve come to terms with the fact that in every interview we ever do for the rest of our lives we’re going to get asked about Dick in a Box.


PLAYBOY: In the SNL short 3-Way (The Golden Rule), you and Justin entertain Lady Gaga with something called the “helicopter dick.” Did you have to explain to Gaga exactly what a helicopter dick is?

SAMBERG: Yeah, I explained it. But she’s not easily shocked. And I think most people know what that is, right? It’s when you’re naked and you gyrate your hips and make your dick swirl around like it’s the blade of a helicopter. Every man, whether he admits it or not, has done the helicopter dick.


PLAYBOY: Your song “I’m on a Boat” was nominated for a 2010 Grammy in the best rap/sung collaboration category, pitting you against such noncomedic performers as Rihanna and Jay-Z. Did it feel like validation, or were you worried Jay-Z was going to kick your ass for pretending to be a rapper?

SAMBERG: I would’ve kicked my own ass if we’d won. We thought it was kind of a joke that we got the nomination at all. I was pretty sure there was no way we’d win. And if we did, then the academy was obviously racist. Luckily, Jay-Z won.


PLAYBOY: Your feature-film debut was in 2007’s Hot Rod, in which you play an inept amateur stuntman. Did you do any of your own stunts?

SAMBERG: None of the crazy shit, but I was going to do the pool jump. There’s a scene where I ride a moped off a ramp, straight up into the air and then straight down into a pool. It seemed easy enough at the time. I told everybody, “I’m just landing in water, right?” But they explained that if I went even three feet too far, I’d hit the other edge and die. Looking back on it, I’m like, Oh my God, of course I shouldn’t have done that. Back then, I felt a lot more confident physically than I do now. Now if you asked me to do a stunt like that, I’d be like, “Nooooo!”


PLAYBOY: How often do strangers tell you they have a great idea for a comedy scene?

SAMBERG: All the time. And it’s not just strangers; everyone is always pitching me sketch ideas. The thing that’s most common—and everyone who works at SNL commiserates about this—is when you’re at a family reunion or the doctor’s office or somewhere, and somebody says, “Careful! Next thing you know this is going to be an SNL sketch.” Yes, of course it is. Just wait till I pitch Lorne Michaels a great sketch idea about a normal conversation about politics at a family dinner. It’s going to kill. I don’t believe anyone gets it worse than Lorne. I think everybody Lorne meets knows somebody who is perfect for the show. “I’ve got a cousin! I went to college with this guy! I know this girl who spoke at a bar mitzvah, cracked everybody up! My doorman is the funniest!”