I ordinarily ignore Andy Samberg around here. It’s not a judgment on him at all – I think he’s incredibly cute and very funny, in a goofy-hot-boy-that-I-would-loved-in-college way. God, I can’t even imagine how hot I would have been for him when I was 19. It would have been BAD. Like, I wouldn’t have been able to stop thinking about him and I would have followed him around, hoping that he would notice me. Gah! Anyway, I usually ignore him because I guess I think that no one else is that interested in him. Prove me wrong! Andy is this month’s “20 Questions” in Playboy, and the interview is charming. I didn’t know he grew up in the San Francisco area, or that he was basically raised by hippies. Here are some highlights from the piece:

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: 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: 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.

[From Playboy]

Am I completely out of touch for not even registering before now what a “helicopter dick” is? That’s SO WRONG. And so funny. Anyway, Andy talks more about Natalie Portman and being nominated for a Grammy and stuff which you can read here. Ugh, I need to stop obsessing over him. I’m an adult! I’m not in college anymore. There’s no reason to stare off into space, fantasizing about what would have happened if I had met in college. He wouldn’t have been into me, I’m sure. But I still would have tried to make it happen.

Photos courtesy of WENN.