Reporter: Diane Sawyer
Producer: Jacqueline Payson
Britney Spears is the most famous 21-year-old on the planet, and one of the richest, raking in about $200,000 a day. And at the moment you can't talk about her without mentioning that night at the music awards the night she pashed Madonna.
After all, this was the girl who promoted teenage purity so seriously; who vowed she'd just say no until her wedding day. But then, maybe the stories from the PR machine were always a bit too good to be true.
And now, a few more myths are about to be shattered.
DIANE SAWYER: Ladies and gentlemen, the most valuable square inch of real estate in the entertainment universe. And this is the girl who owns it, 21-year-old master of the trade. The famous abs, oh.
You're not working them all the time?
BRITNEY SPEARS: Once I start touring, I'll start, you know, doing that.
DIANE SAWYER: And then will she have the perfect body? Not to her.
And you don't like the famous bottom?
BRITNEY SPEARS: The world-famous bottom. Oh, don't say that. That's a very nice compliment. It's so weird, I think sometimes I'm more comfortable on stage than I am in my own room. When I get on stage, it's kind of like your chance to let go and be something you're not, maybe. And it's your time to dream and then I look back and I'm like oh, okay, I just did that, okay.
DIANE SAWYER: Last year Spears reportedly made $39 million, that's about $107,000 per day [US dollars]. So a whole empire can fail if the fans don't follow where she leads. A lot of people don't make it.
BRITNEY SPEARS: Oh, gosh. Will I make it?
DIANE SAWYER: Do you like your voice?
BRITNEY SPEARS: Do I like my voice? I think my voice is okay. I like the feeling that I get when I sing. It's not so much my voice, it's a state that I go into when I sing that I really like. It's probably the one song that really states where I'm at. Doing what I love to do and dancing.
DIANE SAWYER: And the girl who always played it close to the line on how much skin she showed posed like this for Esquire magazine. Consider the line officially crossed.
BRITNEY SPEARS: It's about doing a beautiful picture.
DIANE SAWYER: Is it about shocking people?
BRITNEY SPEARS: About shocking. You know I feel comfortable in my skin. I think it's an okay thing to express yourself. Have you seen … I hate to bring this up, but Kate Hudson, she's 22, she's in sheets. Jennifer Lopez, she poses very provocatively sometimes. Christina Aguilera… What's the big deal when I do it? Like, come on, you know. I don't understand.
DIANE SAWYER: I think everybody always thought you had a different relationship to young girls.
BRITNEY SPEARS: Everyone now, they look back and they're like, "What happened to your sweet image that you used to be?" And I'm like, then when you came out you thought I was too provocative. It's like you can never win. No matter what you do, at the end of the day you can't please everybody, you know. I'm not here to please...
DIANE SAWYER: Have you ever gone further than you wish you had?
BRITNEY SPEARS: No, I don't think so, no. Okay. Now those are a little much. Yeah, those are a little much. That's one picture, I must say, that I felt kind of weird about, yeah.
DIANE SAWYER: Getting burned by the fire she lit herself. It's so easy in her business. Her first deal with the publicity devil was made even before she could read. She was a gymnast turned dancer turned contest star, Britney Spears.
BRITNEY SPEARS: Oh my God. Oh, my big bow and my hair.
DIANE SAWYER: And belting songs out. One of those big Grammy voices.
BRITNEY SPEARS: I was very Broadway.
DIANE SAWYER: Can you still do that?
BRITNEY SPEARS: I'm trying to think. 'They say…' oh, I don't want to sing it, I'm embarrassed.
DIANE SAWYER: Give me one line.
BRITNEY SPEARS: (Sings) ‘They say I'm crazy, got no sense, but I don't care. They may or may not be, but I don't care’. Okay.
DIANE SAWYER: Okay, thank you.
By age 11 she's there on the Mickey Mouse Club with another star-in-waiting, Justin Timberlake. By 15 years old, Spears had signed a major deal with Jive Records. So the factory went to work on her and they had a little song for her to sing. But Spears had a bigger idea, to sing it as a Catholic schoolgirl in knee socks and a tied-up shirt. And now six years later, she's still constantly feeding the publicity monster, as much as she seeks the attention.
BRITNEY SPEARS: Well, I think right now I'm trying to find the balance of being open and at the same time having stuff for yourself. We love Britney.
(All sing) 'Oh baby baby, how was I supposed to know?'
DIANE SAWYER: And then in the past two years, that image has taken a highly-explicit turn as she searched for a new edge. We wondered does she care what her old fans, those kids think … for instance, what about this?
(Sings) 'How could it hurt you when it looks so good?'
BRITNEY SPEARS: When we actually got on stage and we did it, it's like, when you have all those lights you really let go and we really did it.
DIANE SAWYER: You said there's no tongue action here.
BRITNEY SPEARS: Oh, of course there was no tongue, oh gosh no.
DIANE SAWYER: It looked like it. It looked like it was.
BRITNEY SPEARS: We're good actresses here. We know what we're doing. I can see how you say that, because our mouths were a little open like that and it looked like. But no, there was no tongue. I couldn't do that.
BETTE MIDLER: I mean, I know these two ladies don't really give a damn what I say, but I think it's irresponsible in a way.
BRITNEY SPEARS: I think it's a huge pressure to think you have to take the responsibility to be this role model.
DIANE SAWYER: It's one thing not to want to be the role model any more, it's another thing not to know that a lot of young girls are looking at this, a lot of them.
BRITNEY SPEARS: But am I responsible for them? The only person I do worry about, that I want to be a good person for, I think is my responsibility, is my sister. I'm going to be cool for you, okay. I like, I need to, I like being by myself right now. I think it's good for me.
DIANE SAWYER: So who are the dream guys now? Still Brad?
BRITNEY SPEARS: Yes, definitely Brad and, I don't know.
DIANE SAWYER: Ben?
BRITNEY SPEARS: Ben Affleck, he's cute, and I think Colin Farrell's really cute too.
DIANE SAWYER: Are you still friends with him?
BRITNEY SPEARS: Um, we talk every once in a while, but he's very busy right now.
DIANE SAWYER: I followed the kissing and the tabloids and 'are they together, were they just out for a minute?'
BRITNEY SPEARS: No, we're not together. I'm single right now, completely single, so.
DIANE SAWYER: You said recently 'I'm not doing so good with relationships'.
BRITNEY SPEARS: No, I'm not. It's hard for me to let people in sometimes.
DIANE SAWYER: And she always seems to be paying for her teenage comments. We get an interview. See what I go through. She was going to stay a virgin until marriage.
BRITNEY SPEARS: I would like to be able to wait until I'm married.
DIANE SAWYER: And that she didn't even drink. In the past year, a report that she had tried serious drugs at a club. We asked, starting with marijuana.
BRITNEY SPEARS: I've been around people and I've gotten a high off of it and that is enough for me. I cannot, I can't do that. I don't do that.
DIANE SAWYER: Cocaine?
BRITNEY SPEARS: No, I never.
DIANE SAWYER: They left the impression that at clubs that you tried cocaine.
BRITNEY SPEARS: I've experimented, and partying, but never that. I could never do something like that. I'm such a control freak, I would never be able to do something that makes me feel out of… I mean, drinking makes me feel that way sometimes, so I can't.
DIANE SAWYER: And maybe she has another kind of adolescent rebellion. London, insulting fans by showing up late to her movie premiere, no autographs, barely saying hello. In Mexico City, four months later, a finger for the paparazzi. And then five songs into her concert the last night of her world tour, she walked offstage in front of 50,000 fans. It's too dangerous a situation. And it all happens as she's starring as a kind of villain in the tabloid accounts of supposed jealous arguments and then a horrible break-up with her self-proclaimed first love, Justin Timberlake.
You've had a rough year.
BRITNEY SPEARS: It was pretty rough, yeah. Yeah, it was kind of weird. Oh, weird, hello. Oh my goodness, hello. Oh, strong Britney. Yeah, it was a weird time. Oh, can we stop this.
(Sings)'And every time I try to fly I fall without my wings.'
DIANE SAWYER: It's another one of the songs on her new CD. It's called 'Every Time'. She wrote it. Listen to the words.
BRITNEY SPEARS: (Sings) 'My weakness caused you pain, and the sun's smile.'
I was upset. I was upset for a while. We both … I think we were both really young and it was kind of waiting to happen and I will always love him. He'll always have a special place in my heart. He is such a great person.
DIANE SAWYER: But you've said, "I've only slept with one person in my whole life, two years into my relationship with Justin." And yet he's left the impression that you weren't faithful, that you betrayed the relationship.
BRITNEY SPEARS: I'm not technically saying he's wrong, but I'm not technically saying he's right, either. So all this feels really awkward right now.
DIANE SAWYER: Timberlake has made a kind of sport about public retaliation. On a popular morning drive radio show in New York promoting his album, he has a kind of gleeful confession about their very private life.
RADIO ANNOUNCER: Justin Timberlake is in the house. And I just want to ask you one question, did you (bleep) Britney Spears? Yes or no.
JUSTIN TIMBERLAKE: Oh, man.
RADIO ANNOUNCER: Come on man.
JUSTIN TIMBERLAKE: Okay, I did it.
BRITNEY SPEARS: It was a really weird time. There was like talk about our … what we did together and like really...
DIANE SAWYER: Sexually?
BRITNEY SPEARS: Sexually and stuff. And I just felt very exploited and very weird. I was like, why is he going on those shows and they're asking him and he talks. But I'm sure he's like, you know, right, like right now you're asking me about it and it comes right out.
DIANE SAWYER: Talking to your little sister now and the girl who said that she was going to stay a virgin until she got married, do you still think there's something to be said about that?
BRITNEY SPEARS: I think honestly if you can wait until you're married I think you should definitely do that, because it's so much more sacred. That you don't go around sleeping with people. But I mean, I really thought I was going to be with him for the rest of my life, I did.
DIANE SAWYER: How soon? Five years? Would you like to have a guy, a family?
BRITNEY SPEARS: That would be an ultimate dream, I think that will be great.
DIANE SAWYER: Do you think you would wait until you're 30, 40?
BRITNEY SPEARS: I don't want to wait until I'm 30. No. I would love to have a family. That would be when I'm most content. My kids, they become your life. It's not all about you any more and you have a focus. That's so beautiful.
(Sings)’I'm not a girl, not yet a woman’
DIANE SAWYER: Not yet a woman, a woman.
BRITNEY SPEARS: Yeah, I feel like I'm a lot older than what I … or wise, I don't know, from five years ago definitely.
(Sings) 'I'm not a girl, not yet a woman.'