Nov. 4, 2002 -- Justin Timberlake and Britney Spears were the golden couple of teen pop, he the lead singer of the world's best-selling boy band, 'N Sync, and she a belly-baring role model for millions of teenage girls.
But then, in March, Spears, 20, told the British press that she was not "in an intense relationship with anyone." Timberlake, 21, later confirmed the break-up, telling People magazine he had a "broken heart."
Now he is striking out on his own musically too, releasing a solo album, Justified, which hits stores Nov. 5.
As lead vocalist of 'N Sync, Timberlake was one of the most visible of the five group members, but it remains to be seen whether he can make the transition from a boy band pop icon to a solo rock star.
Timberlake does not see his solo effort as a risk. "If it succeeds, then that's great. If it doesn't, then it just doesn't," he told 20/20's Barbara Walters in his first-ever sit-down interview for network television.
A Quiet, Clean Little Boy
Timberlake was raised in Shelby Forest, Tenn., a small town just outside Memphis, by his mother and step-father, Lynn and Paul Harless.
Timberlake says he was a "terror" growing up, but his mother remembers him differently. "He really never was a terror," she said. "The scary thing about Justin is he was such a quiet child that you'd have to go see what he was doing."
She also says he was a perfectionist. "He probably is one of the cleanest people I know. He couldn't stand anything on his shoes or his hands," she said as Justin protested laughingly, "That's enough."
Timberlake remains close to his mother. She is one of his managers, and he says he tells her everything and she is his best friend. "My mother has been there so much for me, and has helped me level things out when things got crazy," he said.
Timberlake even has a tattoo on his back showing an angel holding a banner with his mother's initials. He has six other tattoos, mostly commemorating various of 'N Sync's four albums.
Big Break as a Mouseketeer
Timberlake got his first big break in 1993, at the age of 12, when he was selected as a Mouseketeer for the Disney Channel's Mickey Mouse Club.
He says it was a dream come true: "I remember seeing the show on television and thinking, you know, these are cast members that are together every day and have a ball doing what they love to do. And I just thought, man, what, what an incredible experience that must be."
The Mouseketeers may have been a happy bunch, but they also knew why they were there. "The ongoing joke off camera was M-I-C, see you real soon, K-E-Y, why? Because we get paid to, M-O-U-S-E," he laughs.
One of the other Mouseketeers a young lady named Britney. Timberlake says he immediately fell for her, though, being 12, what he felt was more like an infatuation, he says. "Obviously, the feelings of love weren't as developed as they possibly could be." He did, however, give Spears her first kiss.
Birth of a Legend
When the show was canceled two years later, Timberlake asked his mother if he could join up with four other teens — Lance Bass, J.C. Chasez, Joey Fatone and Chris Kirkpatrick — to form a pop group.
He was just 14, and a musical career would mean no regular high school — just private tutors — and no college. His mother wasn't worried, though, because she knew her son would at least finish high school. "You're going to finish high school if we have to go handcuffed together," she says she told him.
After two years' hard work touring and honing their act in Europe, the group released its debut album in the United States in 1998. Combining soft rock, rap, and hip-hop sounds, it was a smash success, selling more than 10 million CD's.
Timberlake says he talked to each of his fellow group members and has their full support for his solo project. He says each is going in different directions at the moment, but says it will not be the end of 'N Sync. Even if he is a big success as a solo artist, he says he would like to do another album with the group.
Life With Britney
Timberlake and Spears met again when she toured with the group in 1999. This time they fell in love as adults, bought a house together, and made headlines around the world.
Spears has said publicly that she believes that "good morals" means not having sex until you are married. Timberlake told 20/20 he agrees with her and that the couple observed that during their time together.
Timberlake told 20/20 he promised Spears that he would not publicly say why they broke up, in order to avoid fueling speculation and misrepresentation in the media.
He has been quoted as saying something "very bad" happened, and there has been speculation that Spears had a relationship with someone else. But Timberlake declined to elaborate. "We're not perfect," he said. "I don't judge anybody. It's just young love. It's just young love. It was a very intense relationship, that's for sure."
He said he cannot say whether he thinks he and Britney will ever get back together again.
Is There a New Girl?
Since the break-up, People magazine has named Timberlake one of "America's Top 50 Bachelors" and he has been seen partying in nightclubs all over the country. But he denies rumors linking him romantically to pop stars Janet Jackson and Christina Aguilera, and actress Alyssa Milano, saying he is married to his music. "At this point in my life, if you really want to know who my girlfriend is, it's the 13 songs on that CD," he said.
If he were looking for a girlfriend, Timberlake said, he would want someone like his mother, who understands what he goes through in his career. In physical terms, he said the first thing he looks at in a woman is her mouth. "But as far as body parts, I'd probably say I'm a butt guy. I'm not going to fight it. I like some junk in the trunk," he said, laughing.
Music insiders who have heard Justified say that many of the songs — ones that Timberlake co-wrote — are about Spears. Timberlake says only that the songs are about many different people in his life, including her.
During the 20/20 interview, Timberlake sat down with Walters at the piano and played a song, "Horrible Woman", which is not on the album but might become part of his live show.
So, you had your chance to be my lover. I guess you needed something more undercover, And you know that ain't cool. So let's skip the drama, Call your momma And tell her she better just come get you 'Cause frankly baby, you ain't with the gas in my BMW.
I thought our love was so strong. I guess I was dead wrong. But to look at it positively, hey girl, At least you gave me another song about a Horrible Woman.