During that time, he was linked to Scarlett, Olivia Munn, Mila Kunis, Olivia Wilde, Ashley Olsen..who's counting.
Early on, Spears tried to defuse the controversy by preaching abstinence until marriage, and even denied that she was consciously cultivating such a sexualized image.
Justin Timberlake: The two former Mouseketeers started dating in 1999 and ended their relationship in 2002.
Close to 15 years later, fans still have fond memories of the pair who defined young love and made matching denim-on-denim looks iconic on the red carpet.
He was 16 and just starting out in 'N Sync, she was 23 and one-third of the pop trio, Wild Orchid -- talk about robbing the cradle! They grew up together on the Disney show, and began a romance in 1999.
"It was before he got real heavy with Britney," she told Australia's . It all came crashing down in 2002 after Brit allegedly cheated on him, which inspired his hit song "Cry Me a River" off his debut album, in 2011."We spent way too much time being the biggest thing for teenyboppers." She starred as his love interest in his racy music video for "What Goes Around... Then he was spotted visiting her apartment in 2011 (during his brief split from Jessica Biel -- more on that later). That's something only the two of them know since they've never publicly discussed it!