Despite the breakups and heartbreaks of 2002, Britney was as dedicated as ever to her career. She'd been busy travelling the world, promoting her third CD, “Britney.” In this area of her life, at least, she could take charge.

Dan Kenney: Britney Spears honestly was just about the single hardest working person I have ever been exposed to in my life.

Dan Kenney was the music director for Britney's band. That's him on the piano. He'd watched her grow and change ever since the early days of her first hit tour for Baby One More Time.” By her fourth tour she had become the poster girl for a highly sexualized age.

Dan Kenney: Do I think her advisors might have suggested that sex sells? Yes. I do. But did she take that and run with it? Yes.

In fact, Kenney says during that “Dream Within a Dream” tour in 2002, he got the distinct impression that Britney wanted to take even more control over her image and career.

Dan Kenney: She was being influenced by, you know, the managers, the lawyers, the finance people -- also, like, even hairstylists and dancers. She was waiting to kind of break free and to make her own decisions.

That included writing her own music. Dan says Britney had never shown much inclination as a songwriter, until one day when she needed help with a little tune.

Dan Kenney: “You know, Dan, I have this melody.” And she'd sing me this melody. And I have a little keyboard and whatnot. We wrote this bluesy kind of tune called “Mystic Man.”

Then she shocked him by saying she wanted to perform their new piece that night, on stage, right before her song "Not a Girl Not Yet a Woman.”

Dan Kenney: I said, "We just wrote this thing.” And she's like “Yeah. We'll be fine. OK. We'll do it." So she was becoming more gutsy. I think she wanted to become known not just as a producer but as a creator.

Those creative moments aside, Britney's concerts were all about her latest stock and trade, cool moves and steamy numbers. Like this one on a flying platform -- complete with slithering dancers and wet costumes. It was a showstopper for Britney and a sign to her music director that maybe, just maybe, Britney had taken the sexy thing a bit too far.

Dan Kenney: I saw this mother and two little kids on either side of her and she's covering their eyes like this. She's got a horrified look on her face. She's like (gasp)! I came off stage and my crew guy, he gives me a towel and puts his arm around me. And he says, “You do know you're playing keyboards for the anti-Christ, don't you?" And I said to myself “Oh, my God!"

That transformation from bubblegum to bombshell became complete when the queen of shock -- Madonna -- seemed to anoint Britney the new pop princess with a scandalous kiss during the 2003 MTV Video Music Awards. Britney later tried to make it all sound innocent enough.

Britney Spears: I mean, come on, Madonna. If you kiss any girl in the world it has to be her.

Yet even as she glowed from all the attention, it may have been that Britney was starting to have second thoughts about her packaged image. For the first time, Britney, the tightly choreographed pop star, was about to veer off-script. In the heat of the moment, in the dark of night, she shocked everyone with a stealth move.

It was early 2004. She and a hometown friend named Jason Alexander had decided to go for a late night run -- down a Vegas wedding aisle. To some observers it was a sign that Britney's idea of "being in control" meant being a little out of it.

Michael Musto: I think this weekend marriage was Britney's way of breaking out and saying, "I’m going to do what I want to do, even if it's wrong."

But her old music director Dan Kenney saw it differently.

Dan Kenney: As far as marrying that guy, it just represented to me that she wanted some semblance of normalcy. That's what people do. We get married.

Whatever the reason, Britney's mother and managers swooped into Sin City, forcing the two to annul the marriage. After just 55 hours as Mrs. Jason Alexander, Britney was a single woman again, and not too happy about it.

Joe Levy, Editor in Chief, Blender magazine: These were people who had helped her end, forced her to end her first marriage. Whatever enmity she had was lasting. She was pissed off.

As if to get even, she made this appearance a few months later on an L.A. beach with a new man at her side: Kevin Federline.

Brandy Navarre: They went out onto the beach surrounded by paparazzi and just kind of hung out as if we all weren't there, which is funny. And the magazines were just eating it up. The public loved it.

Brandy Navarre is head of X17, which specializes in candid celebrity photos and videos -- better known as the paparazzi.

Brandy Navarre: I think as soon as she started dating Kevin Federline, we said, "Whoa, something big's going to happen here."

What happened was that Britney the pop icon had discovered a new way to entertain the crowds. Now her personal life -- and the celebrity press -- could keep her star power burning bright. But who was her latest act, Kevin Federline, anyway? It turns out he was a backup dancer.

The word was he'd just left his pregnant girlfriend and their daughter to be with Britney. He had traded up in life.

And the woman rich enough, beautiful enough. famous enough, to nab any king on earth seemed to find her prince charming here in homeboy jeans and cornrows. It was as if Britney were daring the world, including her mother and her managers, to question her career – and her taste in men.

Michael Musto: Kevin became an instant pop culture punch line. Nobody was buying this. Nobody respected him. They thought he was a cheesy white rapper with bad hair. He was kind of the biggest joke since Cher's bagel boy.

But if people were tittering, Britney wasn't listening. If everyone thought the new couple was just a joke, let them snicker. Britney was happy to play along and to laugh right back.

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