Playboy Interview: Justin Timberlake

By Playboy Magazine

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Argue all you want, but the case can be made that next to, say, George Clooney (and, okay, Keith Richards), Justin Timberlake is the coolest dude on the planet. The handprints on his bedroom wall alone could seal the deal; he has opened his man cave to Britney Spears, Fergie, Alyssa Milano, Cameron Diaz, Jessica Biel and, if the rumor mill serves, Scarlett Johansson and Olivia Wilde.

Timberlake does okay in other departments, too. As a singer, he has earned six Grammy Awards and sold more than 17 million albums as a solo artist and more than 60 million worldwide from his days with ’N Sync. He is a popular guest host on Saturday Night Live (his “Dick in a Box” video with SNL’s Andy Samberg landed an Emmy and more than 100 million views online) and a favorite on Late Night With Jimmy Fallon. Timberlake is a tequila drinker and weed enthusiast and has a six handicap in golf. He drives fast cars, runs a successful clothing company and, frankly, looks better than you probably ever will. He can dance, too.

Then there’s the exploding movie career. In last year’s The Social Network Timberlake embodies the jittery distractedness of Facebook nation as Napster co-creator Sean Parker. He has two big film comedies this summer—Bad Teacher, opposite Diaz, which opened in June, and the sex romp Friends With Benefits, opposite Mila Kunis, a few weeks later. This fall he’ll appear in the sci-fi thriller Now, a movie about switching off the aging gene.

Not that Timberlake himself could have packed much more into his 30 years. Growing up in suburban Millington, Tennessee, just outside Memphis, he sang in the Baptist church where his father, Randall, was choir director. His parents divorced when he was three, but his mom, Lynn Harless, helped choreograph a career that took Timberlake from Star Search to The Mickey Mouse Club to the boy band ’N Sync (Harless named the band using the last letter of each band member’s first name). Later Timberlake reinvented himself as a grown-up solo artist with such soulful pop albums as Justified and FutureSex/LoveSounds.

Contributing Editor David Hochman sat down with Timberlake at the Chateau Marmont hotel in Hollywood and saw him again backstage at a TV talk show. “What’s cool about Justin is he’s famous just for being Justin Timberlake,” says Hochman, who recently interviewed Helen Thomas for Playboy. “He does many, many things and does them all well. When you meet him, you know how it must have felt to meet the young Elvis or Sinatra.”

PLAYBOY: Let’s start with sex. Your new movie, Friends With Benefits, has lots of it. What was it like letting it all hang out?

TIMBERLAKE: I’d be lying if I said it wasn’t completely awkward. I couldn’t tell you the number of people in the crew watching me and my bare ass, but it was a lot. The producers and I agreed we would shoot a big chunk of the movie before we got down to the sex scenes, which was a good idea. That allowed Mila and me time to get comfortable. It wasn’t that I didn’t want to go all out for this. In fact, when they first gave me the script, this was a PG-13 movie. I didn’t think it was funny enough. I said I didn’t know how you could have a movie called Friends With Benefits without embracing the “benefits” part.

*PLAYBOY: *You and Mila certainly look as though you’re enjoying each other’s company.

TIMBERLAKE: You have to, and we did. We just wanted it to be funny, but we wanted it to look real, too. Most of the sex scenes are actually played for laughs, and she’s such a gifted comedian. There’s a whole scene in which I have to pee during sex, and it gets into how tough that is and how women just don’t understand the completely different parts men have. That was a lot of fun to shoot, but a lot of the time it was just me making a fool of myself. You can’t be shy with comedy even when you’re standing there naked.

PLAYBOY: Was there a penis sock involved?

TIMBERLAKE: You wear the proper ornaments, yeah. But I’m used to it. I shot a pretty explicit sex scene with Christina Ricci in Black Snake Moan. It’s totally weird, but you just jump in and do these things. You rock out.

PLAYBOY: The big question Friends With Benefits raises is whether men and women can have sex without getting emotionally involved. Is that possible?

*TIMBERLAKE: *God, I’m the worst person to ask about that. I don’t know. I don’t think I’ve ever had that type of relationship. I get hooked on every level when I get close to someone. If you build enough chemistry to want to be intimate like that, someone’s going to catch feelings, and usually it happens quickly.

PLAYBOY: Your other big summer movie, *Bad Teacher, *co-stars your ex-girlfriend Cameron Diaz. What were the feelings there?

TIMBERLAKE: It sounds complicated to everybody else, but it wasn’t to us. Honestly, the only thing I was worried about before I said yes to that movie was being asked that question. I knew at some point we’d have to promote the film and people would say, “Oh my God, that’s so weird that you two dated for four years.” I don’t know what else to say except the truth, which is that we’re friends. We don’t talk to each other all the time, but we respect each other, and on some level we’ll always love each other—but in our new capacity as friends . I think the world of her. We did have one very funny scene in Bad Teacher. If you haven’t seen it, I won’t say too much about it. I’ll go out on a limb and say it is the most unique dry humping you’ll ever see in a film.

PLAYBOY: If you do a quick Google search on the women in your life, you come upon a litany of grand theories. A fling with Johansson was supposedly the reason you broke up with Cameron Diaz. Mila Kunis was supposedly the reason you broke up with Jessica Biel. Others insist it was Olivia Wilde. Care to set the record straight?

TIMBERLAKE: None of it’s true, so I shouldn’t even dignify it with an answer. The thing is, I’m not going to sacrifice my friendships with people who are my co-stars I meet in the business. I’m not going to avoid spending time with people because someone who doesn’t know me makes assumptions about what’s going on. That’s bullshit. I don’t know who sits around behind a computer screen making the shit up, but at a certain point you just have to shut it off. I can’t look at the stuff anymore. My life is not on the internet. My life is right here, right now.

PLAYBOY: But it’s no secret you’ve had a string of high-profile relationships. Wouldn’t it just be easier sometimes to have a relationship with, like, the girl from the dry cleaners or something?

TIMBERLAKE: Technically, I guess. But you can’t help who you have feelings for. If you turn it off because someone is famous, then you’re being unfair to yourself. You could walk down each of those roads and find pros and cons. The girl from the dry cleaners is not going to understand how I feel about the work schedule and pressures I have. You probably gravitate toward people who understand your scenario. At the end of the day you just want someone who gets you, who can be a friend. That’s kind of the point of Friends With Benefits. As corny as it sounds, the “friends” part counts just as much as the “benefits” part, if not more.

PLAYBOY: By the way, how many sit-ups does a guy have to do a day to look like you do in those Friends With Benefits nude scenes?

TIMBERLAKE: I did go on a diet for that movie, which mostly came down to not drinking as much beer. And you know, beer is good, so that was hard. I’m pretty thin anyway, but I didn’t want to look like a meathead. I was like, I’m about to be 30, and I’m going to be naked on camera. If I’m going to do this, I’m going to train pretty hard. In the end, I just did more cardio, and I pumped up the stuff I already do throughout the year, such as playing sports. I like basketball and golf and snowboarding, and I do them pretty fucking intensely.

PLAYBOY: Do you do anything half-assed?

TIMBERLAKE: I think people sometimes don’t pay enough attention to what they do. I’ve done well, but the reason is pretty simple: I’ve worked my ass off. Anything I’ve done well has taken many, many hours of preparation. And then the trick, of course, is making that work look invisible. The toughest thing a performer can do is make it look as if it comes easy. You have to devote yourself 100 percent when you’re figuring stuff out, whether it’s with sports or music—or movies, which has been the main focus for me lately.

PLAYBOY: Do you consider yourself more of an actor than a musician at this stage of your career?

TIMBERLAKE: I feel like a rookie in the movie business, that’s for sure. Maybe a little bit of an outsider, too, since I came to it from music. But I think that’s fair. I don’t know that I’ve done a huge body of work that would warrant my not feeling like that. Then again, this past year has certainly opened up a new chapter as far as acting, and I’m grateful for that.

*PLAYBOY: *How much do you think your Saturday Night Live appearances helped pave the way for your movie career? Your hosting gig in May was your fourth, and many of your sketches have gone viral.

TIMBERLAKE: Let me put it this way: My favorite thing in the world was to make people sing—until I made people laugh. Then that became my favorite thing in the world. SNL gave me a place to do that, and all my experiences there have been tremendous. I think it made people notice me in a different way. When you have a sketch that catches fire or goes viral, people go, “Okay, I can see him doing other things besides music.”

*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.

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?

TIMBERLAKE: Absolutely.

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.

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.

PLAYBOY: Any particular fashion regrets?

TIMBERLAKE: God, I feel I’ve gone to therapy just to erase some of them. The cornrows I wore with ’N Sync. That was pretty bad. Britney and I wore matching denim outfits [to the 2001 American Music Awards]. Yeah, another bad choice. I’d probably pay good money to get some of those pictures off the internet.

PLAYBOY: Some people, no matter how rich they are, secretly worry all their money could be taken away tomorrow. Do you ever worry your good fortune may disappear one day?

TIMBERLAKE: Not today. Maybe I will tomorrow, but I’m good now.

PLAYBOY: That must feel pretty solid.

TIMBERLAKE: It makes me feel as though I’m on the right path, definitely.

PLAYBOY: What do you splurge on? Do you shop for private jets on the weekend?

TIMBERLAKE: I haven’t bought a plane. I’m not a splurger, really. I have some cars. I have three Audis. I have a Q7, which is just an SUV. I have a sedan and an R8, which looks supercool, but I never drive it. I used to spend money on shoes, but in the past three years a lot of my money has gone into interior design. I have a place in New York. I redid my house in Los Angeles, which was not cheap. A lot of money goes into art and interior design. My friends saw it when it was finally done, and they definitely oohed and aahed.

PLAYBOY: Okay, let’s play a quick round of Awkward or Awesome. Ready?

TIMBERLAKE: Let’s do it.

PLAYBOY: The Kardashians.

TIMBERLAKE: Awkward.

PLAYBOY: Charlie Sheen.

TIMBERLAKE: Awesomely awkward.

PLAYBOY: Jersey Shore.

*TIMBERLAKE: *Awkward in an awesome way. I’ve never seen the show, but I met them backstage at the MTV awards and they were this fearsome group, storming around the hallway. That looked pretty awesome.

PLAYBOY: Lady Gaga.

*TIMBERLAKE: *Okay, let’s talk about Lady Gaga for a minute. She’s a force. Beyond awesome. I mean, she’s legitimately talented. I’d love to see her come out with another record a couple of years from now that’s completely different, maybe something Tori Amos could do. If I were Lady Gaga, I’d do whatever I wanted, which it looks like she’s doing. She’s just plain old good. But I don’t know what the future holds for her. Her sound is so big. She’s got the outfits and she shocks you, but you kind of wonder how an act that big stays around forever. That’s why I’m curious to see her mix it up a little. I think she’ll continue to make interesting music.

PLAYBOY: How would your career be different if you were starting out now? The entertainment industry has gone through so many changes. Do you think about that?

TIMBERLAKE: I don’t think too much about how my career would be different, but things have definitely changed. Certainly in the music business they have. I started when people were buying CDs. I watched the whole thing transform. I talk about that with my friends a lot. It’s such a completely different industry now.

PLAYBOY: If you’re a performer today, you don’t need the studios. You can get your music or movies or comedy out there on YouTube and make things happen yourself.

TIMBERLAKE: Well, the hardest part for any young performer is to develop what you have. So yeah, with a great video, you can be seen by a couple of million people on YouTube. But if your iron strikes really hot, really fast and you’re not ready for it, then you’re basically fucked. From the public’s standpoint, it’s great. You get to see all this untapped talent. But in a way, I think we’re still in the car-crash phase of this whole sensation. People like to watch weird shit on YouTube. They like to see car crashes. It’s the same way with music. Some of the stuff that comes up is car-crash music, if you know what I mean. There’s not as much legitimate talent because a lot of it is driven by this need to get stuff out there quickly. You gain wisdom about yourself and what you feel comfortable putting out only by developing slowly.

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.


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