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: 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.

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