Timberlake's tour bus is parked in back of the New Daisy Theatre, where his TV special will be filmed later tonight. He makes himself a cup of Throat Coat tea and plops down on the couch to tape a dozen radio-station IDs that will air in the cities he's about to visit on his European solo tour. The conversation turns to smoking cigarettes, and Cuthbert announces that more women are smokers than men. "And that's why there's a blow-job shortage in this country," Timberlake quips. "Y'all are getting your oral fixation satisfied elsewhere."
I decide not to ask whether that's a personal gripe, since Diaz and Spears both smoke. In fact, we don't discuss his sex life at all. I have been warned that he won't talk on that subject, and he tenses up even when I ask what he's learned about relationships from his parents. He offers little more than a facile "I've learned that you have to agree to disagree." I ask him about his first crush, and he says, "I'm not gonna go down that road. Ironically, I caught up with her. So I'm not gonna go down that road."
He is tenaciously private, it seems, because he gets to keep so little to himself. He and Diaz have been trailed by paparazzi ever since they got together this summer. He says that during their trip to Hawaii in September, he had to haggle with photographers in order to get some space alone with his girlfriend. "There was one [photographer] that kept following me," he says. "And I pulled over and went up to his car and said, 'You have a telephoto lens and you still need to drive this close to me? Look, you know I'm gonna be on the beach. You know I'm gonna be around, I'm not gonna sit and hide. But, please, you have the technology to be at least half a mile away from me and a get a great shot. So why don't you just do it that way?" And he did. They still got their shots, and it still pissed me off, but at least they backed off."
He says that the constant harassment has occasionally made him think about quitting the business. "I've said before that I don't want to do it anymore, and that it's just not worth it," he says. "People have said, "Well, that's the price you pay.' And I say, 'Really? Somebody forgot to send me that bill. Do you do what you love to do? Because that's what I do.'" He's not likely to throw in the towel anytime soon, but he admits that he'd like to take on a more behind-the-scenes role when he gets a little older. "I keep joking with my family and friends that I'm gonna retire when I'm thirty," he says. "But I don't even know where I'm going to be next year. Last year was the most tortuous year of my life. And this year, it's as if some higher powers was like, 'All right, you passed that test, now here you go, here you go, here you go.'"
This story is from the December 25th, 2003 issue of Rolling Stone.
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