Man-child in the Promised Land

by Alexis Swerdloff / photos by Cass Bird

"Awk-weird," Andy Samberg blurts out in a voice that's just a bit too loud. Kirsten Dunst, his Ray-Ban-wearing alleged former fling, has unexpectedly walked into Sant Ambroeus, the West Village bistro where Samberg and I are meeting. A little while later, he looks at me and says, ambivalently: "I probably should go up and say hi -- that's what people do, right?"

The 29-year-old Saturday Night Live newbie turned movie star is as goofy as they come -- this is a man, after all, who first appeared and then solidified himself within the American consciousness by creating a hardcore rap about Magnolia cupcakes and, subsequently, for sticking his dick in a box. Despite (or more likely because of) his proclivity for making crass and ridiculous jokes about replacing peg legs on pirates with his dong, he's rapidly become both a part of and a challenge to the mainstream comedy world.

His extreme silliness often gets him compared to a young Adam Sandler (also probably because their names sound so similar), but, says SNL creator Lorne Michaels, "I don't really see that." He continues, "to put it this way, I didn't have a déjà vu moment when I first saw Andy Samberg."

Though much of his schtick errs on the dorky side (it should be noted that he is a major abbreviator -- competition becomes "competish," appropriate: "approps") there is also something very un-awk-weird about Samberg. He's ever humble -- when he found out we wanted him to actually look handsome on the cover, he was frankly shocked -- but not since Jimmy Fallon has there been an SNL cast member capable of even allegedly dating Kirsten Dunst. Maybe it's because he's younger than the rest of the cast, or because he cites Joanna Newsom as one of his favorite singers and looks like the guy sitting across from you on the L train -- whatever the case, girls with tote-bags who wear leggings find him adorable.


Andy wears a customized T-shirt and wristband by American Apparel and tights by Running Funky. Cape, shorts, rollerskates and socks from Austins Wardrobe.

Born and raised in Berkeley, California, the son of a photographer father and schoolteacher mother, Samberg had a relatively normal upbringing. He devoted much of his early years to goofing around and trying to make his two older sisters laugh, and at around the age of eight, came to the conclusion while watching I Love Lucy reruns, Mel Brooks movies and Saturday Night Live episodes, that he would like to be a comedian. In the seventh grade, when he saw Jim Carrey on In Living Color, he realized he could make a career of it. "Carrey's way of being funny was so nailing what I liked. Seeing that dude, it felt like until that point, I was waiting for someone who was really funny in a way that represented me. For me, it was Jim Carrey rolled into that Sandler-Farley thing that was like, ohhhhh my God."

It was during high school that Samberg first started hanging with two like-minded fellows, Jorma Taccone and Akiva Schaffer. Post-college (Samberg attended Tisch in New York while Taccone and Schaffer stayed in California), the three buddies re-teamed in L.A. and pursued low-level Hollywood jobs while making comedy on their own. In 2001 the trio launched thelonelyisland.com, a skyscraper in the pre-YouTube desert, to showcase their comedic talents in the form of digital videos. Many of the clips -- a two-episode-long sitcom, Lonely Island, an O.C. satire called The 'Bu and music videos (be sure to check out "Stork Patrol") -- were inane and well-executed forebears of their future work. The boys got a gig writing jokes for the MTV Movie Awards in 2005 and Jimmy Fallon, that year's host, liked what he saw. Fallon hooked them up with an SNL audition and very serendipitously, all three were hired -- Taccone and Schaffer as writers; Samberg as a member of the cast.

One Saturday night in mid-December of 2005, I was watching SNL when Samberg appeared onscreen alongside fellow cast member Chris Parnell in a so-called "SNL Digital Short." The ensuing rap about two dudes going to see the Chronic -- WHAT? -- cles of Narnia on a "Lazy Sunday" in the middle of winter, while consulting Google Maps and loading up on cupcakes beforehand, was a piece of comedic genius. The next morning I found the video on YouTube and forwarded it to everyone I knew. Apparently, so did a lot of other people.

In the wake of the ensuing hysteria surrounding their video (over one million views on YouTube the day after it aired, a New York Times write-up, "Mr. Pibb + Red Vines = Crazy Delicious" T-shirts for sale on eBay, an appearance on Letterman), it was obvious that we had a comedy revolution on our hands, with the Lonely Island crew (Samberg as its mascot) somehow at the forefront. But it was unclear what was going to happen next.

For a while there, following the short, the Samberg hype sort of died down. There was the Natalie Portman rap ("I don't sleep motherf**ker off that yak and that durbin'/ Doin'120, getting head while I'm swervin'), which had people talking, but not much more. The guys chugged along, regularly churning out the Digital Shorts and showcasing their offbeat man-child ways. Among their shorts, it should be noted, are the two very unsung "Laser Cats" and "Laser Cats II," which star Samberg and castmate Bill Hader as Admiral Spaceship and Nitro, who try to save the world while arming themselves with cats who shoot lasers out of their mouths. Aesthetically, the videos look like a drunken teenager made them. While "LC" and "LCII," according to Samberg, "are the cool Brooklyn of Digital Shorts -- I'll probably be hanged later for saying that," they and their brethren ("Lettuce," "Roy Rules") did not quite take off like "Lazy Sunday."


"I think 'Dick in a Box' really took the pressure off a lot. And by pressure I mean took the pressure off our balls. It really lifted the dick up," Samberg jokes, before getting serious: "And the video 'Dick in a Box' with Justin Timberlake took the pressure off more figuratively. After 'Lazy Sunday,' I was like, 'This is going to be the only thing anyone is ever going to want to talk to me about for the rest of my life.' I mean, I was really happy that we had something that people connected with, but you don't want to be the band that always has people talking about their first album. After 'Dick in a Box,' we were like, 'Ahhh, now we have two things we can talk about.' And then after Hot Rod it was three."

Very soon after the success of "Lazy Sunday," Samberg, Taccone and Schaffer, still numb from the aftermath, were approached by Paramount and Lorne Michaels to make Hot Rod, a film originally developed for Will Ferrell. Though the parameters were not ideal -- they would work from a script already written and get the film made quickly during the summer hiatus from SNL -- the boys jumped on it. "If you wanted to do comedy your whole life and then one day Lorne Michaels says you can make a feature movie to star in with your buddy directing and your other buddy co-starring from a script that you like -- you don't say no," Samberg says. "And I still think we made the right call -- the movie is really weird."

Depending on whom you talk to, Hot Rod is either a terrible stinker or a really strange and wonderful movie that you can't believe they got away with making. Samberg, not surprisingly, is of the second camp. Most critics, alas, were of the first. The film, which follows hapless stuntman Rod Kimble (Samberg), as he prepares to jump his motorcycle over 15 buses to win $50,000 and pay for his stepfather's heart surgery so he can beat the crap out of him, is certainly a head-scratcher. It's full of non sequiturs, inexplicable asides and random '80s film references. Each time Rod gets ready for a big jump, he summons the "totem spirits" -- an eagle, a bottle-nosed dolphin, a housecat and a fox -- which appear onscreen, floating beside his head. On the way to a date, Samberg rides his bike, singing, "Ohhh, when you're going on a date you put on a shirt/ and you ride your bike to the date." A joyous parade leading up to Rod's big jump for no reason at all turns into a violent riot. After mastering a pommel horse routine in the woods in a Footloose-reminiscent dance number, Samberg tumbles down a hill in what is quite possibly the longest and most absurd fall scene in film history. 

"A lot of people don't like a movie that stops making sense -- it's human instinct. When a movie goes off on tangents and is stupid for stupid's sake, that's not appealing to them, because they want to feel like they're invested in something," Samberg says, adding, "I've never been that way."

The film's less-than-magnificent reception appears to have neither Samberg nor Michaels particularly concerned. "I've lived through everything from Wayne's World with Mike and Dana to Tommy Boy with Chris Farley, all the things I did with Ferrell, and even Three Amigos," Michaels says. "Critics just don't like new comedians, and they certainly don't like them if they come from SNL or television. Later on, they revise their opinions and say that so-and-so's later films aren't as good as the first ones. I think the picture will be thought of differently in two years."

Samberg adds, "The movies I've always liked, comedy-wise -- Billy Madison, The Jerk -- always got terrible reviews. When our reviews came in, it was like, 'Oh, we're right on track.'"

Whether Hot Rod goes on to cult film heaven or winds up in the $5.99 bin at Duane Reade, for now all Samberg's doing is getting excited about his upcoming CG-animated film Space Chimps ("I love monkeys and I love space -- it was an easy pitch"), the Emmys ("Dick in a Box" was nominated for "Outstanding Original Music and Lyrics") and going back to SNL in the fall. It's been said that the new season is going to be a lot more Samberg-focused than before, but, Samberg counters, "There's no predetermined anything on that show." He's just happy to be part of the revered institution. "Even though I've had a lot of good stuff happen to me, I'm still so new on the show. I mean, I just got there. The magic hasn't worn off on me -- I love getting to sit in on meetings and see how the show works. I'm not numb to it at all."

In the more immediate future, Samberg has decided he is, in fact, going to head over to Ms. Dunst's table. Once our food is cleared, he gets up, runs his hand through his hair and replaces his plastic-rimmed glasses with a pair of retro shades. "Yeah," he says, "they're prescription."

Assistants to photographer: Colin Simmons and Joan Hernandez * Hair by Sarah Potempa using Aussie products for The Wall Group * Photography intern: Ellen Blaschke * Fashion interns: Eloise Barrow, Kat Stoeffel

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