"Don't be pissed off I'm an actor," Justin Timberlake recently sang, explaining why he's taken a sabbatical from music to concentrate on his burgeoning movie career: "I'm doing me." And yet, some of Timberlake's fans can't understand the crossover: This is the biggest male pop star in the world, and he's set it all aside (Timberlake hasn't even begun work on a new album since 2006's FutureSex/LoveSounds) to appear in films like Yogi Bear and next summer's Friends With Benefits? The fans of his music are so ardent that they're willing to hack his hard drive to dig up unreleased music — but does he have a fan base that's just as eager to see him in a movie? To figure out what kind of future he's got, we talked to industry experts and asked them the question, "If Justin Timberlake were a stock, would you buy, sell, or hold?"
Stock History: Timberlake has made four justifiably celebrated appearances on Saturday Night Live, and his versatility and enthusiasm came as a surprise to many, though it shouldn't have: He honed his variety-show skills as a young member of The Mickey Mouse Club, which produced performers like Ryan Gosling, Keri Russell, Britney Spears, and Christina Aguilera. Still, casting directors took note, and Timberlake was cast as the lead in the 2005 drama Edison, along heavyweights like Kevin Spacey and Morgan Freeman. The virtually unknown film made barely a ripple.
Rebooting his approach and riding high off his second solo album, Timberlake went up for showy supporting roles in films like Alpha Dog and Black Snake Moan (and, in two famous misfires, The Love Guru and Southland Tales). Still, it wasn't until he landed the third-billed role of Sean Parker in The Social Network that real acting accolades began to come his way, and Sony responded with a vote of confidence by placing him in the 2011 comedies Bad Teacher and Friends With Benefits. (He's currently shooting Andrew Niccol's sci-fi thriller Now, where he plays the lead opposite Amanda Seyfried.)
Peers: Garrett Hedlund (26), Sam Worthington (34), Tom Hardy (33), Joseph Gordon-Levitt (29), Ryan Reynolds (34), James McAvoy (31), Taylor Kitsch (29) and Ryan Gosling (30).
Market Value: Unclear. Timberlake's biggest hit was his voice role in Shrek the Third, which took in almost $800 million worldwide, but you can credit him for that as much as you can credit Ned Beatty for Toy Story 3's success. In live action, until he made The Social Network (which has grossed almost $100 million domestically, with Oscar nominations to come), few of the movies that Timberlake supported were notable performers, and many faded fast. And Social Network was sold largely on its real-life story, as well as director David Fincher and writer Aaron Sorkin.
What Hollywood Thinks: Publicists think that when it comes to audience goodwill, Timberlake has nailed his transition from singer to actor-glasses-wearing serious artiste. "His PR? Perfection," said one. "There's nothing wrong. Everybody loves him. He's talented as a singer. He's very down-to-earth, comes across as friendly, nice. SNL helps immeasurably: If you're willing to make fun of yourself, you're golden. And he is."
But does being well-liked necessarily confer movie-star appeal? One rep raised a red flag: "He seems like a guy only women respond to, not a guy's guy. He can do some comedy. I think the question mark is whether men will connect with him. I guess he's made his commitment to his acting career, but time will tell. I have my doubts that guys will respond to him as a leading man."
It's a relevant concern: So far, Timberlake has done best in supporting roles, and all of his bids for leading-man glory have tanked. Last year, he starred opposite Jeff Bridges in an indie film called The Open Road, and despite the fact that it was released just months before Bridges won an Oscar for Crazy Heart, it made a brutal $19,716 in theaters. "He's not exactly a young Clint Eastwood," added the agent. "By that I mean when boys saw Tom Hardy in Inception, they were sold. The other problem near-term is that Friends With Benefits, from what I hear, it's Mila Kunis's movie, not his."
The Analysis: It's undeniable that Timberlake's acting career is heating up; if you thought he was around a lot this year, just wait until 2011, when he's got two summer comedies and a sci-fi thriller to open. Still, he remains a casting question mark for many in Hollywood. Timberlake was a finalist for the lead role in Green Lantern, but it went to Ryan Reynolds, who was coming off an unequivocal live-action hit in The Proposal. Even David Fincher has admitted that he was reluctant to cast Timberlake in The Social Network, fearing that his pop-star fame would prove too distracting.
Some think Fincher should have trusted that instinct. "He's gotten a lot of attention for The Social Network, but to me, the simple fact was that he, being Justin Timberlake, completely took you out of the movie," said an agent. "I mean, there are few pop stars in 2003 that were bigger than Justin Timberlake. It's no fault of Timberlake; he just shouldn't have been cast."
Though the crossover from musician to movie star has been pulled off by plenty of performers like Will Smith and Queen Latifah, few were as famous for their music as Timberlake was at his peak, and few have had a path to stardom that comes with as much baggage (despite the fact that Timberlake has famously dated dream girls like Jessica Biel and Cameron Diaz, many men simply won't warm to a male pop star with a famous boy-band past). As an actor, Timberlake is trying to woo a segment of an audience who used him as a punch line when he was in 'N Sync, and though he overcame that during his transition to adult crooner, it'll be harder for him to convince moviegoers that he's a different person onscreen.
The Bottom Line: In January, Justin Timberlake will be 30. If he wants to be an A-list young actor, it's now or never, so who can hurt him for trying? Indeed, his 2011 bid for leading-man status finds him starting off in a comedic wheelhouse that could work for him without alienating male audiences; instead of going the full McConaughey, he's picked some edgy, R-rated romantic comedies that will help burnish the adult bona fides he may have sacrificed by voicing Boo-Boo in Yogi Bear.
But what comes next? Now is an intriguing thriller, cast with a terrific ensemble including Olivia Wilde and Vincent Kartheiser, and though audiences may not be ready for the idea of Timberlake as an action star, a sci-fi thriller gets the same thrust across in a less alienating way. An Oscar nomination for The Social Network would have helped, but it now looks unlikely; instead, Timberlake will have to keep himself content with accepting romantic-comedy roles and Chris Pine's leftovers. Still, for someone whose other job is being a music megastar, is there anything wrong with steady work on the B-plus list?