When I was a kid, I remember seeing Aerosmith on the cover of Rolling Stone and thinking, 'Wow, they're rock stars,'" says Justin Timberlake. "I mean, they're legitimate rock stars. And when 'N Sync got our first Rolling Stone cover, something didn't add up for me. We were definitely not rock stars." Timberlake was on the cover of the magazine twice with 'N Sync: First, in 2000, dressed in a glittery suit during what could fairly be called his awkward years, and then a year later, as he was beginning his transformation into one of pop music's sexiest twenty-first-century male icons. Neither 'N Sync cover, however, foretold how startling an image overhaul Timberlake would later undergo, or that by January 2003, he would emerge from the world of manufactured teen pop to become a credible R&B solo artist whose debut album, Justified, could reasonably be called hip. "That whole year was weird for me," says the singer, who appeared on our cover twice more in 2003, including a shot with his tourmate that summer, Christina Aguilera. "Before that, I was just a boy in a group. There was a lot of naïveté involved, and we didn't really understand the weight of the phenomenon. Rolling Stone was my first cover by myself, and it was different in the way everything felt different at that time. I felt like, 'Wait, people are really listening.'"
And looking too: The late photographer Herb Ritts played an essential role in unveiling the new chiseled, grown-up Justin Timberlake. Ritts had previously directed 'N Sync's "Gone" video, but the Rolling Stone shoot at the now demolished Ambassador Hotel in Los Angeles was the pair's first time doing a photo session together. "Herb was such a great man," says Timberlake. "There was something about him that made you feel comfortable having your picture taken. It didn't feel gluttonous or irresponsible, because you knew he loved what he did so much that you were going to be taken care of." The pool at the hotel had been emptied by the time Timberlake showed up, and Ritts brought the singer down to the bottom to set up his shot. "He kept saying he wanted to capture something raw and unrehearsed," says Timberlake. "That's a lot of the reason it ended up looking the way it did. Young dude running around shirtless? That could go one way or another. But, being shot by Herb, you felt like you were a piece of his art." Art lovers swooned over the portrait, which announced Timberlake as a grown-up solo artist, and brought him a slew of older fans, male and female. Says Barry Weiss, head of Timberlake's label, Jive Records, "People saw it and thought, 'This isn't just some kid singer in a boy band. This is Paul Newman or Steve McQueen shit.' It was a great part of his maturation, and the fact that it was Rolling Stone elevated his stature as a real artist."
Timberlake admits that when the magazine first hit the newsstand, he had initial concerns about whether agreeing to go shirtless had been a good idea after all. "For like a week solid, I wouldn't even talk about it," says the singer, who's currently at work on a new album. "I was like, 'Holy shit. I'm that guy. I'm that guy! I'm that guy on the cover of Rolling Stone with his shirt off. But then chicks started coming up to me, and I was like, 'Yeah!', as if I had masterminded this whole sex-appeal thing on purpose. I was single at the time too, and I definitely got attention from females in a different way after that. But, hey, that's what Rolling Stone covers are for: They're to get people's attention."
This story is from the May 18th, 2006 issue of Rolling Stone.