PLAYBOY: Justin Bieber seems to have done okay for a guy who started off as a musical car crash, so to speak.
TIMBERLAKE: Justin’s great. He’s obviously a talented kid. I just hope he has a good support system, because I think back on myself wearing the cornrows. It’s awkward growing up in front of the public. Justin’s probably dealing with that on some level now. Somebody like Usher mentoring him is great because Usher is somebody who’s had a lot of ups and not a down that I can remember. He’ll teach him that you can’t just ride this out. You need to have somewhere to go. You need to have a plan, and somebody like Justin Bieber should be thinking about that right now. Otherwise, before you know it, there’s going to be some kid who’s younger than you. We just live in that age.
PLAYBOY: The public is not very kind to the aging pop star. Have you seen the dance-off video going around the internet between Old Britney and New Britney? It shows performances from her early days intercut with performances now. It’s not pretty.
TIMBERLAKE: The internet is a cruel place. What a fucked-up thing to do.
PLAYBOY: She’s had a pretty rough time the past few years.
TIMBERLAKE: I don’t have too much to say about her situation. I can’t remember the last conversation I had with her. But this thing that happens online bothers me—these anonymous commenters. People think they can say anything and it doesn’t matter to people. I’d love to see the people who comment about Britney online say those things to her face, because they couldn’t. Also, in Britney’s defense, if you pulled up a video I did from 2003, I couldn’t do the shit I did then either.
PLAYBOY: But you’ve continued to attempt things that you haven’t done before.
TIMBERLAKE: I owe it to myself to do things that inspire me and not do things I don’t like.
PLAYBOY: That’s a pretty simple formula.
TIMBERLAKE: That’s how you do great work. I look at people like Prince, who, to me, is the greatest musician who has ever lived. He keeps producing, keeps writing, keeps making unbelievable music—all because he’s true to his passion.
PLAYBOY: Have you spent time with him?
TIMBERLAKE: I have, and it was like hanging with the Ghost of Christmas Future. Everything he says, every note he sings, it’s just like, man, that guy is so far ahead of the rest of us. One of my best experiences onstage was at his house during a party. Somebody came up to me and said, “Prince would love if you could sing something with the band.” I said okay. I was kind of drunk, so I was like, “Let’s do the Stones.” Then we did “Miss You.”
PLAYBOY: Hopefully it went better than the time you sang “Miss You” with the Stones onstage. The video of that 2003 Toronto benefit concert made us cringe a little.
TIMBERLAKE: That was terrible. I mean, I got beer cans thrown at me the whole fucking day. That was the most humiliated I ever felt as a musician. Imagine, you get a call from Mick Jagger. “I’d really like you to come and do the Stars for SARS benefit.” You say, “Of course.” Then you get there and the bill is the Stones, AC/DC, the Guess Who. I said, “Is there no one else here in my genre? This could be bad.” I remember saying to my band, “Hey, guys, I don’t know what’s going to happen, so just brace yourselves.” And it was worse than I expected. My set was four songs, 15 minutes, and it was literally raining beer cans and glass bottles the whole time from 500,000 people who wanted to see AC/DC and not my sorry ass.
PLAYBOY: What music is blowing you away these days?
TIMBERLAKE: I like the album the Strokes put out this year. That’s the first thing that comes to mind. Trent Reznor constantly blows me away. I can’t stop listening to The Social Network score. He’s just a genius. Anything Jack White does. Every time he does something I’ll be there, front and center, ready to buy it. I’m not the biggest fan of popular music right now. I really like The King of Limbs, the Radiohead eight-song set. It sounds like Thom Yorke has been deejaying more because some of it feels that way. There’s a song on there called “Separator.” It’s like, put that song on, get in the car and stop thinking. Radiohead has the ability to make you feel you’re cramped up in a closet and then, all of a sudden, you burst out into an open wheat field and everything turns sepia or something.
PLAYBOY: What about in movies? Who would you like to work with?
TIMBERLAKE: It would be fun to do something with Ryan Gosling because we’ve known each other since we were 10. Picking movies is more than hiring actors. Who’s going to be leading the ship? Who’s the director? What is the script saying? What story are we telling?
PLAYBOY: Do you have a dream project in the back of your mind?
TIMBERLAKE: Not really. I know the movies I love, and I’d like to make movies like them. Ferris Bueller’s Day Off, E.T., The Goonies, Reds, The Music Man. Seeing Fight Club changed the way I watch movies. It was so much smarter than anything I’d ever seen before, which is why working with David Fincher was such a bucket-list move. Making movies that can touch people the way any of those films did would be all I could hope for.
PLAYBOY: Why do some celebrities crack and fade and others, like you, just keep on keeping on? Have you figured that out?
TIMBERLAKE: I don’t know, but I can speculate if you’d like me to.
PLAYBOY: Yes, please.
TIMBERLAKE: I’m not sure it’ll be anywhere even close to accurate. I think it’s about process. If you care about the process of what you’re doing, you can care about the actual work. You’ll stick around. The other thing is, you always need to be learning something new. In whatever I’ve done, I’ve always looked at myself as a beginner. Hopefully I can continue to do that for the next 30 years as I grow into an older man.
PLAYBOY: What kind of old man do you want to be?
TIMBERLAKE: That’s so hard to say. I can’t picture my life five years down the line, let alone 20 or 50. I know I want to be physically active. My [step]father always said he wanted to live long enough to golf his age, and I think that’s a worthy goal. I’d like to be able to ski down a hill or snowboard when I’m 65. Personally, I’d like to be more patient and perhaps learn to sit still by then. Mostly I hope I can still connect with people, still have new experiences, still make an impact on the world.