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.”