PLAYBOY: One of the standout moments of that episode was when you called your mom practically in tears. You’ve said before that you two are best friends and that you “grew up together.” A shrink would have a field day with those comments.
TIMBERLAKE: Sure, I can see how that could raise some eyebrows. I mean, it’s not meant to be taken literally. I don’t think we grew up together, but we’re still close. I just turned 30, and I think you get to a point where you start to separate things. You sit there and go, Here are the things about my parents that are in my blood and here’s what has come from experience. I’m more conscious about breaking the chain. My mom has a lot of determination, and I think I got that from her, which is great. But as I said, I think I took it too far and it made me miss out on some things.
PLAYBOY: Like having a childhood?
TIMBERLAKE: Not the childhood stuff so much.
PLAYBOY: Going to college?
TIMBERLAKE: It’s more like whatever it is you find out about yourself in college. I never got the experience of sitting back at that age and saying, What do I actually want to do right now? Because, again, I was already committed—to a band, to an album, to a tour, whatever. I’ve thought about this a lot recently. Maybe I’m too much of an open book for things like this, but you’re catching me at a moment when this is what I’m learning most. For years I was constantly chasing, chasing, chasing. Then I thought, Well, maybe I’m actually running from something rather than chasing something. Maybe something is chasing me and I’m trying to get away from it. Who knows? Whatever it is, I feel I’m just getting to a point in my life where I’m looking around, going, There’s a lot to enjoy if I can just sit still, actually stop and take more time. That’s what I’m trying to do this year. I did four movies in a row and finished the fourth—the movie Now—on my birthday. Ever since, I’ve been retreating, doing nothing, listening to music, enjoying myself, playing golf.
PLAYBOY: Of course, even your golf game has type A written all over it. You could have taken lessons at a public driving range, but instead you hired Tiger Woods’s former coach, Butch Harmon. Any tips to share with the weekend golfer?
TIMBERLAKE: Butch’s whole approach is that it’s way better to have a short swing that gives an accurate shot than to try to put the ball in. He would make me practice hitting 30 or 50 balls with a six iron just to get used to hitting low punch shots. Half swing, swing low, don’t even finish the swing. When I showed up, I was scooping the ball up with great big swings because I thought that’s how you get the ball into the air. Using shorter swings lets the club do what it was made to do.
PLAYBOY: If you could be guaranteed 100 percent anonymity for one day, what would you do?
TIMBERLAKE: Oh God, probably just go for a walk somewhere. I’d go walk around Paris or Rome. Or if I was really anonymous, maybe I’d do something outrageous like commit arson or rob someone or find all those fuckers who wait outside my house and go outside their houses and stalk them. A day of anonymity would be cool, though. Just to go to a store and not be hassled.
PLAYBOY: How many times a day do random strangers ask if you’re bringing sexy back?
TIMBERLAKE: It happens all the time. I can tell what’s sticky in my repertoire by the comments I get when I walk through the streets of New York. For a year or so after that song came out, all I got were “SexyBack” comments. After “Dick in a Box,” it was UPS guys coming up to me with “Dick in a Box” jokes. Or people wanting to friend me on Facebook after the Facebook movie. You can complain about it, but to me it’s flattering. It means something I did touched people enough for them to respond that way. Even if it happens 20 times a day, you have to be okay with it. The alternative is nobody talking about you, and that’s certainly not good.
PLAYBOY: You’ve also influenced people with your fashion choices, including your clothing line, William Rast. You wear a certain hat or sneaker and suddenly everyone’s wearing it. Does that ever feel weird?
TIMBERLAKE: I don’t think about my influence on stuff like that too much. I see a lot of young guys dressing more like I should have been dressing when I was their age. Robert Pattinson dresses properly. He’s more adept than I was. But I don’t know. I don’t think there’s been one specific person other than Sinatra who has influenced my style.