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Andy Samberg doesn’t toot his own horn. Talking for two hours in the empty, preservice dining room of the Sunset Tower Hotel in West Hollywood, the Brooklyn Nine-Nine and Lonely Island star says nothing that resembles a brag, humble or otherwise. Not even in jest. It’s funny because, of all the people self-aggrandizing in Hollywood, few of them have had the impact on pop culture that the 36-year-old comedian has over the last decade. (Also, this is the guy who once joke-rapped the most horn-tooting line ever: “Suck my own dick—like a boss!”)

A repertory player on Saturday Night Live from 2005 to 2012, Andy’s best known for the SNL Digital Shorts that he shot with his junior high friends and Lonely Island comedy partners Akiva Schaffer and Jorma Taccone. Heavy on rap and other youthful pop culture references, they spoke to the Internet generation and helped the sketch show break through online. At SNL, there’s life before and after December 17, 2005, when the group’s hard-rap-meets-soft-white-guy-mundanity music video “Lazy Sunday” aired. The breakout short went viral overnight, making the trio web celebs and racking up five million hits on YouTube before NBC Universal had the video taken down and moved to its own SNL and Hulu sites.

“There had always been shorts on SNL, but Andy and the guys brought a genuinely fresh and timely take to that form,” says former cast member Chris Parnell, who co-wrote and rapped on “Lazy Sunday.” “Andy, Akiva, and Jorma’s musical/hip-hop/comedy skills took many of the shorts to a mind-blowing level and were a major factor in giving SNL an online presence.”

With showrunner Lorne Michaels’ blessing, Lonely Island, which had been making acutely aware, comedic “fake rap” songs and videos for years, borrowing from artists like Ghostface Killah (“Stork Patrol”) and Mobb Deep (“The Heist”), followed up “Lazy Sunday” with more wildfire hits and three albums. Their silly, self-deprecating singles “Jizz in My Pants,” “I’m on a Boat (featuring T-Pain),” and “Just Had Sex (featuring Akon)” all went platinum. In 2007, Lonely Island even won an Outstanding Original Music and Lyrics Emmy for “Dick in a Box,” their send-up of ’90s R&B with Justin Timberlake (the statuette actually has the song title etched on it). On July 17, 2012, the group’s YouTube page hit one billion views (at the time of writing, it was nearing one and a half).

So, when I ask Andy if he considers himself an SNL legend, I’m only half-joking. The Bay Area native (he was raised in Oakland and Berkeley), dressed casually in jeans, a yellow 3rd Lair skate tee, Air Max 87s, and an A’s cap, recoils in modesty. Andy, who continues to express amazement that he ever made it onto SNL, the show he fell in love with at age 8, will only concede that his run “didn’t go terribly.” Which is perhaps the polite way of saying it went fucking phenomenally.

Life after SNL hasn’t gone terribly, either. In January, Andy won two Golden Globe Awards for his Barney Miller-esque Fox cop sitcom Brooklyn Nine-Nine (Best Actor – Television Series Musical or Comedy; Best Television Series – Musical or Comedy, as a producer). One of the main reasons that the show, which premiered September 17, 2013, and is currently airing its second season, is a success is the endearing, rakish goofiness that Andy brings to the lead role of man-child Detective Jake Peralta, which plays superbly opposite Andre Braugher’s stern, cold Captain Ray Holt. Chelsea Peretti, who co-stars on the show and grew up with Andy in the Bay, describes him as “chill” and “professional” on set, but it’s clear that his presence provides the levity needed for a sitcom to come off: “When we are in the bullpen, Andy makes lots of faces at me across the room that remind me of why we all got into this business—to make faces.”

Around the time Andy was holding up two Globes like the golden bo’s in his zack, Fox signed the Lonely Island view-billionaires to a development deal to circumvent the expensive pilot system and nurture new comedy properties to run across the company’s varied web and television platforms. “In the most plain terms, they gave us money to shoot things with people that we trust,” explains Andy, who is now, more than ever, actually like a boss.

For three childhood friends who started out making lo-fi comedy rap videos, the deal is another huge achievement, and it promises to pay off for Fox, especially if Andy collaborates with creators the way he does his boys. “Even when you’re furious at him and want him to die, he somehow manages to get you out of your bad mood,” says Jorma. “Usually it’s just him saying the same joke over and over and over again until you laugh, but hey, whatever works. You need positivity to make comedy. Andy’s got that.” He’s just not bragging about it.

What’s the best Halloween costume you’ve ever worn?
One year I was in L.A. with my buddies Kiv and Jorm and we were going to some Halloween party in Silver Lake. We were super broke, all packed into an apartment, and I had a bunch of crap in a box, like old clothes from high school, so I decided to be the kid from your cabin at summer camp who everyone hated. I had a green cotton turtleneck that was way too big and baggy, billowy fleece pants, and Tevas with wool socks. We went to this party and I walked in and no one knew it was a costume. I tried to say hi to some girls and they looked at me like I had rabies. [Laughs.] Finally, at the end of the night, someone asked me what my costume was. I told them, and they were like, “Oh, that’s incredible,” and told all their friends, but it was too late.

Do you have plans to dress up this year?
I’m sure for the show. I like dressing up for shoots and stuff but I’m not the die-hard Halloween guy. Seven years of SNL kind of kicks the wanting to wear costumes out of you. But I’m hoping it’ll come back.

What’s the best slutty costume for guys?
Depends on your bod. If you’ve got a rockin’ bod, probably a gladiator. Falls into the old toga tradition. If you don’t, probably just Rick Ross or somebody who’s really confident.

Did you say Ross because you were on a Complex cover together?
Oh no, actually it’s because I just watched Chris Rock’s BET monologue and he had a joke about that, too. That dude [Ross] smokes. That [photo shoot] was the first time I’d ever seen someone have a personal blunt roller. That dude’s job was just to roll blunts and hand them to Rick Ross. That was pretty fucking baller.

Weed carrier/blunt roller is a common job in rap. Definitely something for your résumé.
[Laughs.] I would be so fucking psyched to put blunt rolling on my résumé. “Speaks three languages, paragliding, blunt roller.”

Your résumé is already pretty strong. Do you consider yourself an SNL legend, revolutionary, or luminary?
No. Never. Never say that. What am I, an asshole? [Laughs.] I only can look at it through my own perspective, which was, “Holy shit! I worked at SNL and it didn’t go terribly.” When you work there, you’re in the shadow of literally everyone. It’s also impossible to be cocky or even confident about being a cast member there because you know that the show’s fan base is so wide and that, even if you’re someone’s favorite on the show, someone else watching hates you. It’s like a sports franchise: Everyone’s got their pick and everyone thinks they know who the weak link is and what should be done differently, and that’s what makes the show fun.

Who did you identify as your haters?
I can’t spend time on that. Although...this is unrelated but, on the drive over here, I saw a dude on the street wearing a T-shirt that said, “HATERS MAKE ME FAMOUS.” I found it funny because he wasn’t famous, so the shirt was just a lie. [Laughs.]

Maybe he was asking them to make him famous?
Yeah, there should’ve been a comma and a question mark then. “HATERS, MAKE ME FAMOUS?” Like, do me this solid. [Laughs.]

There is no proper stage in life to wear that shirt.
Yeah. If you wear the shirt and you are famous, you’re a dick.

On SNL, you had the good fortune to not only play the god Nic Cage but also act with him. Did that experience add to the Cage legend or humanize him?
It certainly didn’t debunk the myth. He was super charming and nice but he still came across pretty cool and badass and on the wind. We finished and walked off and he shook my hand there on the stage and was like, “Pleasure doing business with you.” And then he was gone, like Keyser Söze. [Laughs.] He left and I was like, “There goes the motherfucking man.”

You’ve been tremendously successful fake rapping. What other things are you good at faking? Orgasms?
No need to. I know how to get it done. There’s certainly nothing that I fake as good as rap. On Brooklyn Nine-Nine I have to pretend I’m a cop. I guess since I won a Globe I can say I’m a good fake cop. But let’s be honest, I’m not. [Laughs.]

What have you done with the Globes?
They’re just on a shelf, hanging out together, kickin’ it. I can’t believe I have awards. It’s so weird. I never thought after I got my Most Improved Player soccer trophy that I would ever win any trophies, but, “There’s a lot of things they don’t have an award for.” Drake likes to point that out. [Laughs.] There has been a rash of songs about trophies recently. There’s also the Future one [“I Won,” initially titled “Trophy Wife”]. Why are people so obsessed with trophies all of a sudden?

“I would be so psyched to put blunt rolling on my résumé.”

A coddling culture of participation trophies?
These are adult men, though, talking about trophies a lot. Drake, it seems like he’s talking about the Grammys. Future seems like...trophies. It’s like he sees the girl similarly as he does winning a Little League tournament.

Now that you have Golden Globes, what crazy star demands are you going to make on set?
Man, probably just gonna be like, “Can I get a water?” I’ll just ask for a water out of nowhere like it’s nothing!

Would you ask Andre Braugher?
No, I’d never ask Braugher for a water, but I would get Braugher a water and he would get me one if I didn’t ask because we’re friends. There’s no award for that—getting your friend a water. That was a callback and probably the best joke I’ve had this whole time. [Laughs.]

Have you gone on any ride-alongs to perfect your fake policing?
We’ve done the slightest amount of training with cops or ex-cops who’ve shown us basics. I shot guns recently, though. I did some skeet shooting with a shotgun. Friends in Oregon have a house near the river and they had a whole skeet setup. That was fucking awesome. I hit a bunch of them. I had a pretty good percentage. It’s so satisfying. It’s one of a few things I can do to fulfill my lifelong dream of being Sarah Connor from Terminator 2, just pumping a shotgun.

Prior to Brooklyn Nine-Nine, you did seven years of stand-up comedy, then seven years on SNL. Seven is supposedly God’s divine number. Coincidence?
[Laughs.] It’s gotta be a coincidence.

What was your nightmare stand-up performance?
There’s a youth hostel in L.A. where they would do shows. I went there when I was still new to stand-up and not very good, and it was dollar-beer night. Kiv and Jorm actually came with me to be sweet and we hung out. The hostel had me on last and I got hammered before I ever got on the stage. Finally, they called me up and I was just eating shit and I looked down at the audience and in my drunk mind it was like, “They don’t even understand what I’m saying! They’re all just from other countries!” I was the fucking asshole on stage like, “Does anybody speak English?” The cardinal rule of comedy is, if no one’s laughing, it’s your fault, not their fault. I was so hammered and bombing so hard that I forgot the cardinal rule and it got very uncomfortable. But there were two people in the audience laughing real hard, and that was Kiv and Jorm. [Laughs.] They always point back to that moment for me like, “Man, you sucked that night.”

And all these years later you’ve got a deal developing comedies for Fox. Does that technically make you, Akiva, and Jorma “suits”?
Of a sort, yeah. But we’re pretty cool suits so far. I mean, if I were making comedy and I got a call from Akiva or Jorma saying, “Hey, come shoot your thing. We’re gonna give you minimal notes and you get to make it,” I don’t see that as anything but positive and creative. We have an office, so in that way we’re suits, but it’s fucking awesome.

What’s the vibe of your office?
There’s more than one gaming system.

Are you trying to make stars or work with known comedians?
There’s no mandate. If it seems like a good idea [for a show], it could be somebody who no one’s ever heard of, or it could be Eddie Murphy, if he wants to. Which he doesn’t, but it could be. But it won’t be.

So, headline: Eddie Murphy is working with Andy Samberg.
Please don’t. I’ll get to answer that question for the next year at press junkets. [Laughs.]

If there is a hell, what Lonely Island song plays there on a loop?
If you’re gonna be driven crazy by one of our songs it would be “Shrooms,” which is a very short song on our first album. I like the song, but if you heard it probably more than two or three times in a row you’d want to tear your eyes out.

You’ve described your comedy as childish. How much of that has to do with you playing soccer instead of getting bar mitzvahed and never actually becoming a man?
Very little. [Laughs.] I’m not sure what drew me to that kind of comedy but I think it’s the same way certain people are born and their mind gravitates toward medicine. Obviously, what I do is significantly less useful.

As an unabashed fake rapper, do you care if a rapper is “real” and actually lives the life they rap about?
I certainly would be a hypocrite to say that I do care. [Laughs.] I like to think that the stuff we do, we’re making it obvious that it’s a joke. I don’t have grounds to take issue with it. If I were to put myself in the shoes of a rapper who came from nothing for real, and then there were other people co-opting the culture that is created because you came from nothing, taking that and trying to act like it is their own in earnest, I would take issue with it.

Would you yoke them up?
I wouldn’t even know how to begin yoking someone up. You’re not gonna get me to say something stupid. [Laughs.] I’ve dealt with this conversation way too many times. I’m a white comedian who does fake rap songs.

“Three hundred children grinding, just the funky sweat smell in the auditorium. That’s the power of Jodeci.”

You see right through me. You, Akiva, and Jorma have fake rapped about your dicks a lot. What do you think about guys like Jon Hamm and Michael Fassbender who complain about people focusing on their junk too much?
I have no thoughts on that. [Laughs.] I wouldn’t even purport to know what the right thing…. [Laughs.] Jon’s my buddy, so if he’s annoyed people are saying too much about his dick, then he’s annoyed people are saying too much about his dick. That’s none of my business. But I made a bunch of jokes about Fassbender’s dick at the Spirit Awards when I hosted a couple years ago and those jokes killed, so I was glad people knew he had a big dick at that time.

What’s left for Lonely Island to say, dick-wise, now that you’re all married?
“Diaper Money” is where we’re taking it. We were trying to remain true to where we’re at while also making the dumbest thing possible, and that’s what came out of it. That one was definitely for the older heads. We’ve gotten a lot of love on “Diaper Money” from married dudes and dudes with kids. My dad weirdly likes it—that creeps me out a little bit.

There’s no denying the realness of a song about buying diapers and occasionally having sex with your wife.
We were laughing when we were writing, like, “This is Borscht Belt comedy put to a pretty trappy beat. Like, ‘Take my wife, please!’” But none of us are disgruntled. We’re all super well-adjusted and happy in our lives.

As close as you three are, when does the wife-swapping begin?

Best year in the best decade! What is your quintessential ’90s moment?
I always think about my junior high dance, everybody grinding to Jodeci and thinking about how we were all literally children and how weird that would’ve been to look at as an adult. Like, 300 children grinding to Jodeci, just the funky sweat smell in the auditorium. What were we doing? But that’s the power of Jodeci. [Laughs.]

What scary movie freaked you out the most growing up?
The Shining, by far. Gore, I don’t like watching it, but The Shining is just creepy. When the girl turns into the corpse lady? That was the [moment] that fucked me up the worst.

That’s a horrible way for a boy to learn about sexuality.
Dude, I worked part-time at the United Artists movie theater in Santa Cruz [during college] and we showed Species 2 and that was sexually fucked up! I watched it because we had it there and I was disturbed—and I was in college! People came in with their kids, and I was like, “What is this 6-year-old little dude gonna think about sex walking away from this movie where he sees an astronaut dude, who’s been touched by a space rock, have sex with a prostitute whose belly immediately grows and then alien shit explodes out of her?” That’s your first vision of sex. It’s so irresponsible; it must have been so scarring.

It’s not like, during the height of HIV/AIDS education, kids needed anything else to make them paranoid about sex.
I agree. Kiv and Jorm and I always talk about how screwed our generation was because we were right in that pocket of time between the ’80s and the comeback of glam and rock ’n’ roll. Everyone dressed like TLC. Don’t get me wrong, TLC are beautiful, but a bunch of super baggy overalls and condoms? [Laughs.] There were no tight jean shorts on any girl in my entire high school experience. It was a lot of covering up, everyone scared. And correctly so at that time. Everyone needed to be educated on that stuff, but there were no Dazed and Confused outfits going on. There were no hunky dudes in tight shirts and girls in little jean cutoffs. That didn’t exist in Berkeley, California, in the early ’90s.

Trick-or-treating in Berkeley, did any hippies ever give you treats laced with weed or anything?
No, there were no creepers. [Laughs.] I’ve never been dosed. I’ve eaten brownies. I don’t dig weed food, it lasts too long. You never know the [potency] level of it and you get twitchy for like six hours. That’s bullshit.

What was the worst thing you got while trick-or-treating?
Apples. Can’t eat them. No parent is gonna let their kid eat an open apple. In Berkeley, I’m sure it was somebody being like, “Let’s give them a healthy alternative!” Which is admirable but just way out of touch. The best by far, there was a nice house we’d walk up to in the neighborhood where the people didn’t want to deal with handing out candy, so they would leave a bucket with full candy bars and a note that said: Please take one. My dickhead friends and I would roll up and just dump the whole thing into our bags and take off. If you’re not gonna bother saying hi to the kids then don’t expect us to play by the rules.

Devil’s Night is creeping up, which means a lot of houses are about to get toilet papered, which is fun but also a waste of good paper. Is it fair or foul for the homeowner to reuse the TP?
If your house gets TPed, it’s fully fair game to recover that TP, re-spool it, and use it in your everyday life. You gotta be careful about sap—that could be a bad situation.

Maybe you request only the quilted toilet papering of your home?
That would be a sad concession, if you had a sign outside your house that said, “Hey, I get it. I suck. You’re gonna TP my house. But if you’re gonna, just give me the double quilt.” If you’re at that point in your life, if you’ve hit rock bottom in that way, might as well have a little dignity.