The Complicated Life of Pop Superstar Justin Timberlake

In December 2006, he and Cameron Diaz split after nearly four years together. Their relationship had begun after they met at the Nickelodeon Kids’ Choice Awards, and it became one of his most visible romances after Britney Spears.

The breakup closed an important post-boy-band chapter in his personal life. Diaz had connected him to a more adult Hollywood world, while his music career had only grown bigger during their years together. But almost immediately after that relationship ended, another one began moving into place.