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!”