PLAYBOY: Your first two solo albums sold more than 8 million copies each and basically made you the biggest pop sensation on Earth. What was driving you?
TIMBERLAKE: The first half of my 20s I felt I had to achieve, achieve, achieve. I think a lot of men do this. I’m not saying just because I turned 30 I don’t battle with this. I still battle with it. But in my 20s I had to do everything. I needed everybody to understand me and respect what I was doing. I remember putting out my second album [2006’s FutureSex/LoveSounds]. When I put out the first song, “SexyBack,” radio thought I was a joke. I couldn’t let that go, so I started calling radio program directors. I’m pretty tenacious like that. I was like, “This is my record. Give it a chance.” There wasn’t any of my signature falsetto or anything. I’d say, “I know it doesn’t sound like me, but just please give the record a two-week period or even a one-week period. Just let the music get out there. If the callback is good, keep playing it.” I was that relentless. During the second half of my 20s I started to ask myself, What am I doing? What have I built, and how do I continue that for the next 10 years? For some reason, in the past year I’ve done so much work I feel as though it’s backfired. I’m looking around now and I’m like, Where am I running? I’ve been running so hard for so long. I’ve seen the inside of more arenas than your average basketball player. Like I said, I’ve had that experience on tour sometimes when I think, I don’t feel like going onstage. I have no energy right now. I’m sick, I barely have a voice. But you do it anyway. You feel obligated to go out because all those people showed up. You end up performing. But at some point in my life I wish I had learned to say no. From the beginning of my career, I was a guy who said yes all the time to everything.
PLAYBOY: What were you like as a kid?
TIMBERLAKE: I grew up in a small town, and because I started working when I was 10, I was kind of looked at as more of an oddity. I would sing at the talent shows at schools and go around town doing different things, but it was more like, “That kid’s a freak.” You hear a lot of stories about child prodigies, child actors or people whose parents pushed them really hard. But I was the one begging for the stage. That made me kind of stand out in good ways and in weird ways. Not a lot of 10-year-old Caucasian kids were running around Millington, Tennessee, singing Stevie Wonder and Al Green songs, which were the songs I felt most connected to.
PLAYBOY: It’s interesting. If you listen to your voice when you sing and when you speak, you sometimes sound black. You’ve got so much soul the NAACP nominated you for an Image Award this year for The Social Network. Do you ever feel as though there’s a black guy trapped inside you waiting to come out?
TIMBERLAKE: Dude, I’m not touching that shit with a 10-foot pole! All I can tell you is I grew up in the South, where everything’s just a little bit thicker. The accents are thicker, the air’s thicker.
PLAYBOY: But clearly you have an affinity for black music and black culture. How else to explain the pitch-perfect “History of Rap” routine you did with Jimmy Fallon last year?
TIMBERLAKE: That’s the music of our generation, man. We were impersonating those rappers. We weren’t trying to be black. Listen, you’re touching on a deep issue for me. It’s bringing up stuff from my childhood. I grew up near the town where Martin Luther King was assassinated . It has always been a very segregated place. When I was a kid people would ask me what I hated most, and I would always say racism. It always comes up, and it always came up regarding my style of performing. I wasn’t cool with the white kids because they thought I wanted to be black. And I wasn’t cool with the black kids because they thought I wanted to be black. So I was looked at as a traitor and an intruder or an imposter. I had to find solace in just being me.
PLAYBOY: As 11-year-old “Justin Randall,” you rocked Star Search with a twangy country number. Did you cry when you lost?
TIMBERLAKE: No. It was just a TV show. I got there and they said, “This is the song you’re singing and this is the outfit you’re wearing.” I knew what the score was. I’m sure American Idol is the same way.
PLAYBOY: How do you think you would have done on Idol?
TIMBERLAKE: Probably not very well. I grew up with a voice that was different. It seems the point of American Idol is to find singers who fit America’s mold of what a talented person should be. That bothers me. I don’t know whose place it is to tell somebody he or she is good or not. Everybody is just different. It shouldn’t be a contest.
PLAYBOY: What was in the water on the set of The All New Mickey Mouse Club that turned so many of those Mouseketeers into stars?
TIMBERLAKE: A really good casting director, I’d say. What’s funny is I didn’t know at the time that the people around me would go on to so many great things. The exception was Christina Aguilera. She was the prodigy. She could sing better than the adults who had huge deals at the time. We always felt she was going to become Whitney Houston or Mariah Carey or whoever she wanted to be. And also Ryan Gosling. I thought he had charisma that was just beaming, which has turned out to serve him really well as an actor. Even now I still root for that family of actors. I still love to see people from those days making good on their talent. It’s a special connection.
PLAYBOY: Any moments of debauchery from those Disney days you can share?
TIMBERLAKE: It was silly stuff mostly. We weren’t into anything too dangerous. Ryan and I were partners in crime on that show, and I remember one time we skipped school, took a golf cart and rode to the Honey, I Shrunk the Kids set. We got milk shakes. Those are the kinds of badasses we were.
PLAYBOY: You’ve talked openly about using drugs, smoking marijuana. Are you still a pot smoker?
PLAYBOY: Is it a creativity booster? I read you were stoned for much of the time you made Justified.
TIMBERLAKE: The only thing pot does for me is it gets me to stop thinking. Sometimes I have a brain that needs to be turned off. Some people are just better high.
PLAYBOY: You put MTV’s Punk’d on the map. In the first episode Ashton Kutcher’s team pretended to be government agents seizing all your property, including your dog, because of unpaid income taxes. You nearly cried and ended up calling your mom. Is it true you were stoned at the time?
TIMBERLAKE: Yeah. I actually stopped smoking pot for nine to 10 months after that. I was so stoned. If you ask my friends, if they’re honest they would probably say that’s the only way to get me as dizzy as I was. What you didn’t see from the episode, because it was a 45-minute affair cut down to 10 minutes, was me showing up and being like, “What the fuck are you people doing on my property? Get the fuck off my property! Get the fuck out of here!” Then they started rattling off my parents’ address, and I was like, “Holy shit. Hold on a second.” I mean, everybody was got good on that show—me probably the best.