In 1988, when Madonna earned her first Grammy nomination, Justin Timberlake was 7 years old. Now, he's telling her what to do.
Katie Couric: It must be hard on some level to have someone like Madonna have someone like you work with her. She'd be like, you know, "I've got sweaters older than you."
Justin Timberlake: Well, I won't tell her you said that.
Couric: Was it hard to click with Madonna at first, at all?
JT: Well, I don't know that it was hard. It's kind of crazy to me that I get paid to sort of tell these people my opinions. 'Cause that's really what a producer is, is just a really good coach.
Justin is good coach who happens to have sold 16 million records of his own. Right now, everyone seems to want a piece of him.
Couric: They put a lot of trust in you, and I guess they have to be pretty vulnerable too. I mean to say "Hey, here I am. Help me."
JT: It's very personal to have that experience with someone. You're coming in and she had her notebook of poetry and ideas and she wanted me to take those ideas and put melody to them and craft songs and an album.
Couric: Were you intimidated by her at all?
JT: No, no. She's short, so I wasn't afraid at all.
In the seven years since he left the mega boy band *NSYNC, Justin's worked with a who's who of the music world, including Reba McIntyre, Duran Duran and T.I.
He's repeatedly returned to his collaboration with super-producer Timbaland, with whom, Justin says, he shares a musical kinship.
"We definitely have a crazy chemistry in the studio," he says. "I guess it's like two painters go in and somebody slaps a color on a canvas and the other one starts working with it."
These days, producing is what's really got Justin jazzed. He's even got his own record label and has signed his first artist - Esmee - a singer he found on YouTube.
"You go in the studio and the artist is there… and they need something rock solid to bounce all of their ideas off," he says. "Your job is just to take the talent and hone it in, and advise them on how to attack it."
So what sorts of things inspire him now?
"I'm constantly inspired by anybody who just doesn't care about what's going on. Who says, 'Well, I'm going to take a left turn here."
Like fellow Grammy nominee .
JT: Wayne strikes me as somebody who's enjoying it.
Couric: His friends call him "Weezy." I'm kidding.
JT: Yes, I've heard that. Wow, you guys are tight, you and Wayne. [We are!] Well, when I heard you were doing a Grammy special, I was like "I want to see Katie and Wayne in the same frame. That's just two people..."
Couric: You wouldn't put together.
JT: Let's just say who wouldn't normally show up at high tea together. Let's just put it that way.
Now Justin's making another creative move into movies -- not blockbusters, but small, independent and challenging films like "Alpha Dog" and "Black Snake Moan."
Justin tells Couric he actively looks for roles, but things also come his way. How seriously is he pursuing acting?
"Very seriously," he says. "I think pop culture has done a number on creativity because, for me to make that statement, I get that reaction, 'Really?' You know, it's like yeah, why wouldn't I? I sort of feel like I have a day job and so this becomes a hobby... it becomes something that I can really plunge into with full creative eagerness."
He's also plunged into TV comedy. Justin's raunchy "Saturday Night Live" comedy skits have been big hits. He says he makes a point of not taking himself too seriously.
Couric: So what motivated you to do that fine musical number "(Ahem!) in a Box?"
JT: Well, I mean, let's talk about it. I happen to think it's a thoughtful holiday gift.
Couric: It was funny, but it was so crude. I mean come on... Did your mom see that? Did she think it was funny?
JT: Yea. You gotta meet my mom. She's a pretty edgy chick!
Then there was the recent "SNL" sketch in which he portrayed a dancer auditioning for Beyonce's "Single Ladies" video.
"That was on the spot. I was in New York. And Andy [Samberg] of 'Bleep in a Box' fame said, 'You know, Beyonce's on the show. And so, have you seen the 'Single Ladies' video?' And I said, 'I saw a piece of it.' So he sent it to me, and I called him back and I said, 'We're auditioning for this video, huh?' And he's, like, 'Exactly.'"
"Put a grown man in a leotard and that's just already funny," he tells Couric. "And she was a great sport for playing along as well."
"They told me that she was having reservations about the sketch. I put the full outfit on and put a robe on and walked-- and you know, knocked on her dressing room [door] and walked in and just dropped the robe and, I kinda stood there and stared off into space. Actually she said 'I can't look anywhere but your face right now!' That's what she said!"
Justin's taking his latest role more seriously, creating a character to promote his booming fashion business.
"The idea was to create a trailer for a movie that didn't exist, about this renegade couple and the clothes kind of were just in these mini-films," he tells Couric. "It was kind of "Badlands" meets "Bonnie and Clyde" meets McQueen..."
Justin showed off some of the latest designs from his William Rast clothing line at its L.A. factory.
"Not to sort of say anything bad about anybody, but there were just a lot of celebrity clothing brands. They sort lend their name to something, but not really their creativity. This was the opposite -- to lend my name as much as we really wanted to lend our creativity, me and my best friend."
Justin and his childhood friend and business partner, Trace Ayala, named the line for their grandfathers.
JT: William is my grandfather's first name and Rast is (Trace's) grandfather's last name.
Couric: So it's kind of an homage to your grand dads.
JT: An ode if I may.
Justin doesn't like to talk about his personal life. It started with Britney Spears and their very public breakup. Since then, he's been linked to some of the most glamorous women in the world: Cameron Diaz, Scarlett Johansson and currently, Jessica Biel.
But there's one true love in Justin's life that he's more than happy to discuss: golf.
Golf Digest magazine says Justin ranks No. 15 among famous musician golfers. He's even got his own PGA Tour stop, the Justin Timberlake Shriners Hospital for Children Open, which had its first event in Las Vegas last fall.
"The beneficiary of the tournament is the Shriners Hospitals - that's philanthropy at its best. You're talking about any person under 18 years old comes into this hospital and for nothing gets the best health care in the world," he tell Couric during a golf outing, where he gives her pointers on her drive.
"I think with each project, whether it be a film, an album, or a song, or a season to come up with designs for a fashion label or producing, whatever it is, what I have naturally done is find a specific muse for each thing and I just go from there," he says.
"I think that from what I'm hearing from you, sort of the secret to your success is to stay a fan of everything... a fan of life almost," adds Couric.
"Absolutely. I think that's the key," he continues. "I mean it makes you a better person to begin with, but I think it makes your art better because I think you become open to the possibilities."
"I would say right now it's pretty good to be Justin Timberlake," says Couric.
"It doesn't suck," he replies with a big smile.
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