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.
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.