PLAYBOY: You made a bunch of not-so-great movies earlier in your career. How did you go from those straight-to-video duds to the caliber of movies you’re making now?
TIMBERLAKE: Honestly, when you’re making a movie, you never say, “Oh, this one’s going to suck and go straight to video.” When you’re in it, you think you’re doing the best work you can do. You’re surrounded by people who are working hard. Everybody’s hopeful. It’s only a year later when you realize, Wait, what was that exactly? If anything shifted for me, though, it was the realization of how important it is to work with smart people. That takes a lot of the guesswork out. Just being in the room with David Fincher and Aaron Sorkin for my first reading for The Social Network, I knew things would be different—even though I felt I had totally botched the audition. I botch a lot of auditions. But the next thing I knew I was on the set. It was surreal. This may sound strange, but I don’t have aspirations to be a movie star. I make movies because I enjoy the creative process. Just to work with people like Fincher and Sorkin or to trade lines with great actors has been more surreal than anything I’ve accomplished in my music career.
PLAYBOY: That’s saying a lot. You’ve had a pretty surreal music career. It’s been five years since you recorded an album. Do you ever miss making music?
TIMBERLAKE: You go through these spurts when you miss it. In a perfect world I’d love to be able to involve myself in music and films as they come and go. But I’m always writing music, always thinking about ideas for songs.
PLAYBOY: Do you have an album’s worth of music hidden away somewhere?
TIMBERLAKE: No. I don’t have a single song ready to go. People keep asking me when a new song or album is coming out, and I don’t know what to say. Music is not my focus right now. It may be someday. It could happen next month or next year, but right now it’s not where it’s at for me.
PLAYBOY: Do you ever worry the audience may not be there if you wait too long? We certainly saw that happen with your old friend Christina Aguilera last year.
TIMBERLAKE: Maybe it’s blissful ignorance, but I don’t relate a time frame with what I do. If it’s time to make another album, it’s time to make another album. It may never be time—who knows? You should watch the documentary Still Bill.
PLAYBOY: That’s the Bill Withers documentary, right?
TIMBERLAKE: Yeah, and I’ve never watched anything else that made me feel someone was speaking not just to me but for me. He puts into words exactly how I feel about music. People asked Bill Withers all the time, “Why did you stop doing music?” Which is what I get asked all the time too. He said, “I don’t know what to say, because I didn’t stop doing music. I just started doing something else.” He also quoted Thoreau: “The mass of men live lives of quiet desperation.” Only Bill added, “I want to know what it feels like for my desperation to get louder.”
PLAYBOY: What does that mean to you?
TIMBERLAKE: Well, I relate to that because it means you need inspiration, you need to hear something loud inside yourself before you can create anything. Unfortunately, the business of music is what taints an artist’s desire to make music. I don’t want to paint a picture of being jaded, because I love making music. I honestly love it. But there is a level where making music becomes a total life-sucking commitment. For instance, to do an album and a tour, you have to be absolutely certain that whatever you have to say is from the heart, because you’re going to say it a thousand times—and on nights when you don’t feel like performing. You need to feel inspiration to get to a level where you’re performing like that. But I haven’t felt that level of conviction the past few years. And without that conviction it’s crazy to put yourself out there.
PLAYBOY: Is there a scenario in which you would ever sing an ’N Sync song again in public?
TIMBERLAKE: I don’t think so. It would have to be a really special scenario. I still talk to the guys occasionally. I probably talk to Joey [Fatone] and Chris [Kirkpatrick] more than J.C. [Chasez] and Lance [Bass]. I’d say I text back and forth with Joey once a month.
PLAYBOY: Off the top of your head, what’s the wildest moment you recall from ’N Sync’s heyday?
TIMBERLAKE: Man, I could tell you a thousand stories. I remember girls running after the buses in the hundreds. We’d do an open-air festival in Germany and there’d be 60,000 people there. We’d finish playing, the band would be putting the gear up, and we would be trying to do a quick out, which is what they call it when you leave the stage before the band stops playing. We’d get on the bus and there would be 250 to 400 girls waiting to run after us. I distinctly remember Joey Fatone singing the theme song from The Goonies while this particular pack of girls was running. It was just crazy.
PLAYBOY: What was it like being 17, 18 and having 400 girls chasing you?
TIMBERLAKE: I hate to disappoint you, but I was the youngest one in the group, so the other guys were getting more of that action, and they were protective of me. I think I was the one who cared about what we were doing onstage. My role was, we’d come offstage every night and get a DVD of the show, just like an athlete watching tape from a game. We’d get on the bus, and I’d go, “Okay, here’s what we did right; here’s what we did wrong,” and we’d fix it for the next day. But yeah, the girl stuff definitely was a heavy part of it, and it would play with your mind. I remember looking down once—we were playing Madison Square Garden for an HBO special—and this girl put her arm out. She had a mural of me tattooed along her whole arm. I just remember looking at it and thinking, Holy shit, that’s never going to come off.
It was a time: the concerts, the fans, the music. Plus, it wasn’t just us. It was that whole factory we came out of—us, the Backstreet Boys and Britney—we were all together. It was bigger than any one of us and bigger than any of the groups. Everybody was selling a gazillion records at the same time. You couldn’t keep what we were doing on the shelves. It was bigger than bubblegum. Sometimes I think back on the time we did five nights at Giants Stadium. That was the moment I just looked around and thought, There’s nowhere for this to go but down. It’s never going to get bigger than this.
PLAYBOY: What’s the secret to commanding a very large crowd?
TIMBERLAKE: It’s not about commanding them. It’s about bringing them toward you. It’s your job to make everyone in the audience feel as though he or she is in your living room. When I’m onstage it’s my mission to make people feel comfortable, not feel in awe. I want them to feel as though they’re singing and performing with me. Even if I’m on a stage, the audience should feel as if they’re on the same level with me.