ONE

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?

ANDY 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 standup in LA. I started having literal dreams, like 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.

TWO

PLAYBOY: Your shaggy hair is one of your most distinguishing features. Does your contract forbid you from cutting it?

ANDY SAMBERG: I’ve heard that before. That’s a total rumor. Ny hair’s short now, isn’t it? And I haven’t heard a word from anybody about it. Nobody even seems to notice. So I guess my hair was 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.

THREE

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?

ANDY SAMBERG: I’ve had my share of both. Actually, I don’t feel like I’ve ever dumped anyone. It’s never been “You know what? I’ve decided that I don’t like you.” It’s usually about the circumstance. I had a girlfriend in college, then I transferred because I wanted to go to film school, and the long distance made it 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, Okay-dokey, I can tell that I was really important to you.

FOUR

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?

ANDY 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.

FIVE

PLAYBOY: Adam Sandler plays your father in the recent film That’s My Boy. What type of father would he make?

ANDY SAMBERG: He’s more of a godfather figure. Once you’re rolling with him, he just calls and tells you that you’re doing stuff. I’m in this animated movie with him called Hotel Transylvania, and I literally found out about it by getting a phone call from him. He was like (in an Adam Sandler voice) “We’re doing a movie about monsters and you’re gonna be the guy.” And I was like, “Okay, sure.” I remember when I first got the job at SNL, I was just 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.”

SIX

PLAYBOY: You’re playing a hedge fund manager in That’s My Boy. Do you know anything about that line of work?

ANDY SAMBERG: An old friend of mine from summer camp, Willis, is a hedge fund manager. I texted him before the movie started and said, “Hey, I’m playing a hedge fund manager. Can you give me any tips?” It was more a way of saying “What’s up” to him. And he wrote me back this impassioned diatribe like “You’ve got to be cut-throat and merciless and willing to make the move that no one is willing to make!” And I was like whooooooa, easy buddy! (Laughs.) It’s a fucking Adam Sandler movie. They’re not going to get too deep into the psyche of my hedge-fund character. He was all too ready to let me into his world, which I appreciated. It seems stressful. And that’s coming from a guy who works in live television.

SEVEN

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?

ANDY 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 where they had kisses just to make the audience go “whooo-hooooo!” And I always hated that. Unless it’s for a joke, there’s really no point to it. So in that regard, I would say Scarlett was my favorite, because it was funny and gross. It was that scene where I played Kuato, the head from Total Recall that’s coming out of Bill Hader’s stomach, and she was 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 that the audience definitely didn’t want to see happen.

EIGHT

PLAYBOY: You were raised in Berkeley, California by parents you’ve described as “hippies.” Were they actually hippies? Were they pot-smoking, bellbottom-wearing, long-haired peaceniks who smelled of patchouli?

ANDY 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 was like “I’m going to grow my hair long because it’s what they don’t want me to do.” He likes to brag that he came of age in a time when you could still 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.

NINE

PLAYBOY: You have two older sisters. Were they kind to you, or were you mercilessly tormented?

ANDY SAMBERG: They tormented me, but in girly ways. It wasn’t like being beaten up by an older brother. 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 the baby. They’d essentially make me into their human doll. 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?

TEN

PLAYBOY: You were voted the class clown in your high school. Did that title come with bragging rights?

ANDY SAMBERG: Not at all. For one thing, all my friends were just as funny as me, if not funnier. And remember, I went to Berkeley High, and being voted the best at anything was not something you bragged about. We had this friend who was six foot five, super buff, the blonde 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.

ELEVEN

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?

ANDY SAMBERG: That are better than Monkey Vs. Robot? I highly doubt it. That was our high water mark. I feel like I brought a certain je ne se quois to the role of monkey. All the movies I made during that time were sort of the blueprint for the digital shorts that the Lonely Island guys and I would end up doing at SNL. One of my favorites, and one of the dumbest films I ever did, 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. And at the end, a woman’s voice whispers the name of the cologne (whispers) “Cooooock.” (Laughs.) We did the label so the “CK” of Cock was bigger, so it looked like the Calvin Klein logo. My film professor at the time hated it.

TWELVE

PLAYBOY: Why did he hate it?

ANDY 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.

THIRTEEN

PLAYBOY: You became pals with Mark Zuckerberg, the Facebook CEO, after impersonating him on SNL. Is that typical? Do you become buddies with everybody you impersonate?

ANDY SAMBERG: Not at all. I got lucky with that one. He invited me to give the keynote address as him at the f8 summit in San Francisco, which was crazy. I like him a lot, he’s a nice guy. I don’t know if my impression of him is really all that good. If you look at us, we could basically be cousins. And we both have “berg” in our last names. I don’t know if that means anything. I’ve played three guys with “berg” in their last name on SNL. There’s Zuckerberh, Jesse Eisenberg, and Mark Wahlberg. I think sooner or later I’m going to have to do Ryne Sandberg from the Chicago Cubs. Just so I can say I’ve done everybody, all the bergs. I’ve always wanted to do Sandberg anyway. That’s what you call some low-hanging fruit.

FOURTEEN

PLAYBOY: Your first digital short for SNL, Lazy Sunday, became a huge hit on YouTube, getting over 5 million views. Is the Internet still the best source for original comedy?

ANDY SAMBERG: I think it is, yeah. Most of my inspiration comes from YouTube. The digital short we did with Jonah (Hill), with him getting hit in the nuts repeatedly with a tennis ball, that came from something we saw on YouTube. We jacked the whole thing. It was like a sports-science show, and they were playing it straight. “We wanted to see what his heart rate would be when he took a shot to the gonads.” I don’t know if it was a joke, but the show seemed like the real deal. I genuinely don’t know. Also, I did this short called Seducing Women Through Chess, which was a complete rip-off of an amazing video I saw called Seducing Women Through Magic. It’s one of the most unconvincing things I’ve ever seen in my life. Poorly edited, poorly acted. It’s just fantastic.

FIFTEEN

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 Levin to sing about having romantic feelings for an Iranian dictator. What’s the secret to coaxing celebrities to sing less than flattering lyrics?

ANDY SAMBERG: With Natalie it was easy. It was all her idea. She loves filthy rap. She’s a big Li’l 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 very skeptical, because we thought of her the same way everybody else did. You know, she seems so sweet and innocent. But she was like, “No, you don’t understand.” And then she broke into some Li’l Kim song, just started rapping verses for us, the filthiest lines I’ve ever heard. We were taken completely aback. We were like, “Oh, wow. Would you be willing to do something like that?” She said yeah, so we were like, “Come back in an hour.”

SIXTEEN

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?

ANDY SAMBERG: I heard that 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 dildo inside of it. Like a realistic looking dildo. And I was like, “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.” Yeah, I probably am. That’s the closest I’ve come to seeing an actual human penis inside of a box, thank god.

SEVENTEEN

PLAYBOY: You’ve done several music videos at 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?

ANDY 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. There’s never a time when one of them is like, “Hey man, I’m gonna take off. Catch you later?” Everywhere they go, they’re together. But the funny thing is, Justin and I have become inextricably linked because of these videos. We’ve come to terms with the fact that every interview we ever do for the rest of our lives, we’re going to get asked about Dick in a Box.

EIGHTEEN

PLAYBOY: You performed Dick in a Box with Timberlake at Madison Square Garden a few years ago. What’s it like singing in front of thousands of screaming teenagers?

ANDY SAMBERG: It was exciting. There were like 18,000 people in the audience. It was nothing like on Saturday Night Live, because you can see them all out there. It’s more immediate, more “This is real. This is happening.” The only thing that bummed me out was how out of tune I was. As soon as Justin and I came up through the middle of the stage, into a spotlight, which was like the coolest thing ever, the crowd went crazy, which was a huge relief. But about halfway into my first line, my earpiece fell out. So I couldn’t hear anything. I started singing in a register one and above what the song actually requires. I was wildly out of tune in front of 18,000 people, which is probably the only time I’m ever going to be in front of 18,000 people again.

NINETEEN

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?

ANDY SAMBERG: Yeah, I explained it. But she’s not easily shocked. And I think most people know what that is, right? Every man, whether he admits it or not, has done the helicopter dick. I’m right about that, don’t you think? Everyone has done it for his lady at least once. 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. I think everyone has either done the helicopter dick or pat-a-cake. Have you heard of that? It’s when you’re slapping your penis back and forth like you’re playing pat-a-cake.

TWENTY

PLAYBOY: Your song “I’m on a Boat” was nominated for a 2010 Grammy in the Best Rap/Sung Collaboration category, pitting you against non-comedic performers like Justin Timberlake, Rihanna and Jay-Z. Did it feel like validation, or were you worried that Jay-Z was going to kick your ass for pretending to be a rapper?

ANDY 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 wasn’t any way we’d win. And if we did, then the academy was obviously racist. But luckily Jay-Z’s “Run This Town” won, which was clearly the best song in that category.

TWENTY-ONE

PLAYBOY: You feature film debut was 2007‘s Hot Rod, where you played an inept amateur stunt man. Did you do any of your own stunts?

ANDY SAMBERG: None of the crazy shit, but I was going to do the pool jump. I didn’t know how to ride a moped at all when we started shooting, but I trained for a couple of weeks and started to feel cocky about it. There was a scene where I went off a ramp, straight up into the air, and then straight down into the pool. It seemed easy enough at the time. I told everybody, “I’m just landing in water, right?” But they explained to me 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. I was feeling a lot more confident physically back then then I do now. Now if you asked me to do a stunt like that, I’d be like “Nooooo!”

TWENTY-TWO

PLAYBOY: Last year you were the host — or Chief Shark Officer — for the Discovery Channel’s annual Shark Week. What’s the secret to swimming with sharks and not looking terrified?

ANDY SAMBERG: I don’t know. I may not’ve looked it, but I was definitely terrified. We shot a bunch of wraparounds down in the Caribbean, and I remember floating out in the water on the back of a surfboard, with 15 to 25 reef sharks swimming all around me, eating. The people on the crew told me nothing bad was going to happen; the sharks were only going to go for the chum, they weren’t going to go for me. But at a certain point, they threw in so much chum and it got so frenzied that some of the sharks starting banging the tip of their noses into me, into my chest. And a few of them took really big bites of chum right in front of me. Like, I saw their teeth. It was scary. I kept saying to the director, “Can’t we just do this with CG?”

TWENTY-THREE

PLAYBOY: Were you ever in real danger? They wouldn’t have put you in a situation where you could’ve actually been harmed, right?

ANDY SAMBERG: I think there’s only so much they can control. And here’s the craziest part. One of the professional guys who swims with sharks, who was an adviser on Shark Week, apparently about a month after we shot my wraparounds, he was out there again and got attacked. A shark, probably one of the sharks that was swimming around me, bit this guy’s face or arm or something. So apparently I dodged a bullet. I did say to all my friends before I left, “If I die while shooting this thing, it’ll be one of the funniest reasons a comedian has ever died.” I’m pretty sure I’d be one of the only moderately famous people ever to be eaten by sharks. It’s almost worth it. I’d corner the market in the “that guy who got eaten by a shark” jokes.

TWENTY-FOUR

PLAYBOY: Mark Wahlberg didn’t seem too happy about your impression of him. He made a joke on Jimmy Kimmel about breaking your “big fucking nose.” Was there real tension between you?

ANDY SAMBERG: Not at all. That whole feud between us was definitely planned out in advance. I knew it was coming. I don’t think I’ve ever legitimately upset somebody by impersonating them. I’ve never had anybody come at me and say, “Fuck you and your impression!” But the silence can be pretty deafening. You almost always know if somebody loves it because you’ll hear about it, so when they don’t say anything, it’s pretty obvious they weren’t happy. People ask me all the time if I’ve ever gotten death threats from (Iran President) Mahmoud Ahmadinejad for the Iran So Far video. I never have, weirdly. I don’t know if he just doesn’t watch SNL or he doesn’t understand it.

TWENTY-FIVE

PLAYBOY: How often do strangers tell you, “I have a great idea for a comedy scene?”

ANDY 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!”

(This story originally appeared, in a slightly different form, in the July/ August 2012 issue of Playboy magazine.)