NEW YORK -- When Justin Timberlake tried out for the role of Sean Parker in "The Social Network," director David Fincher had a particular line from Aaron Sorkin's script in mind. Sean, the former Napster executive who schools Mark Zuckerberg in the ways of Silicon Valley, is a slick seducer: "He was described in the screenplay as moving through the room like Frank Sinatra," Fincher recalls.
Known best for his stint in the epochal boy band 'N Sync and the smash solo career that followed, Timberlake had at the time nudged music toward the back burner, concentrating on acting instead. Scuffing up his teen-idol image, he'd taken roles in dark dramas like Nick Cassavetes' "Alpha Dog" and Craig Brewer's "Black Snake Moan," both released in 2006. Fincher had been particularly impressed by Timberlake's turn hosting "Saturday Night Live" that same year.
"Every time he came on it was, like, man, this guy's good," he says. "He was magic, so effortless. With Justin, you want to see what he's going to do next. And I felt you needed that for Sean."
As Timberlake read for the part, Fincher was convinced he'd found his Sinatra. "But there was the question of whether he'd topple the apple cart," the director recalls. "Everyone thought he was too famous." In the end, Fincher's initial enthusiasm won out. "We finally decided, just because he's perfect doesn't mean we shouldn't cast him."
Timberlake, 30, recounts the moment he learned the news.
Today Timberlake's status as a credible movie actor has gone from something directors fret about to a seeming fait accompli. Many reviews of "The Social Network" praised Timberlake's performance, and when the New York Post reported that he was quietly campaigning for a best supporting actor Oscar nomination, the news sounded much less outlandish than it should have. It wasn't so long ago, after all, that Timberlake was widely considered a frosted-tipped curiosity, one-fifth of an elaborately harmonizing and dancing teen-pop machine and one-half of a post-pubescent power couple with his girlfriend Britney Spears.
Now, after one of the more remarkable show business makeovers, Timberlake oversees a small media and fashion empire, the most recent addition being a stake in MySpace. On the movie front he has delivered two of his highest-profile performances in the comedies "Bad Teacher" and "Friends With Benefits," which comes out Friday. This fall he will star in "In Time," a sci-fi thriller directed by Andrew Niccol, writer-director of "Gattaca" and writer of "The Truman Show." The big question about Timberlake's career is no longer whether the 'N Sync guy can act, but rather what kind of actor he wants to be.
"I don't want to make that decision," Timberlake says.
In conversation he is expansive, but when the topic of his actorly ambitions arises, Timberlake begins a game of cat and mouse. Were there genres he'd especially like to explore?
"I don't think in genres," he says, demurring.
What classic roles did he think of and say, I'd love to play something like that? "Once an actor makes a role his own, it's kind of hard to imagine what you'd do with it."
Was any strategy whatsoever guiding his choices? "Of course," he says. "Early on especially, I turned down a lot of scripts that were targeted to a demographic I already had. It's about being patient, and having something in the back of your mind about not getting pigeonholed."
Timberlake's desire to remain unfixed as an actor likely stems from his time with 'N Sync, which fused him in the public imagination to a single, cartoonish role. With the group he enjoyed an era-defining success (selling more than 11 million copies in the United States, 'N Sync's "No Strings Attached," from 2000, is the biggest album of the '00s) that burned fast but bright, threatening to reduce him to a punch line and relic well before he'd turned 25.
Unlike his band mates, Timberlake managed to start a critically and commercially successful solo career, making state-of-the-art R&B-tinged pop. Even then, he remembers frequently thinking to himself, "I don't want my whole life to be defined by this moment," and he added that he has "no idea" when he'll make another album.
"I've never turned my back on music," he says. "I just want to do other things."
Timberlake traces his mercurial tendencies to his childhood in Shelby Forest, Tenn., a Memphis suburb where he grew up idolizing Dean Martin, Gene Kelly and, you guessed it, Sinatra: "guys who were entertainers across the board," he says. Music came naturally to Timberlake, who recalled hearing songs on the radio as a kid, "picking up a guitar and figuring them out." But he also loved trying out jokes and impressions on his parents and their friends. "When you're young and you make adults laugh, it triggers some chemical," he says.
Timberlake's real breakthrough moment as an actor came, improbably, on "SNL" in 2006. Andy Samberg, looking to involve Timberlake in a digital short, pitched him on an R&B spoof with an unprintable title and lyrics about gift-wrapped genitals. Going on to garner nearly 30 million YouTube views, the short unambiguously demonstrated that Timberlake could put a self-mocking distance between himself and the guy on the mike, not to mention give Samberg a run for his hip-doofus money.
Physical ease is one of Timberlake's clearest assets as an actor, honed over all those years he spent dancing onstage. Fincher points to a wordless montage in "The Social Network" in which Sean holds court at a Japanese restaurant: "There's no dialogue, but you can see it in his eyebrows, in his hands. He's this impish leprechaun who's taken over the night."
In "Friends With Benefits," a romantic comedy about two pals who try to incorporate sex into their friendship, Timberlake has his biggest role yet, playing a hotshot art director with intimacy issues. Will Gluck, who directed the movie, says Timberlake was actively involved behind the scenes, "helping to rewrite the script" to make sure his character "felt just right."
Gluck wanted the rapid-fire banter between the leads to evoke old Tracy-Hepburn vehicles, and Mila Kunis, who acts opposite Timberlake in the film, says he kept her on her toes: "He's so unbelievably quick. He was constantly cracking me up."
Movies are Timberlake's priority these days, but he also owns, wholly or in part, restaurants, a fashion line called William Rast, a record label and even a golf course. Discussing his involvement with Specific Media, the company that just bought MySpace, he said he'd put his own money into the purchase (declining to reveal how much) and explained his role, roughly, as that of a "connector" and brainstormer.
"I'm not a capitalist," he declares. "I just love ideas, getting chances to create."
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