Britney Spears and Justin Timberlake were one of the most famous couples of the early 2000s. They met while working together on The Mickey Mouse Club as teenagers. Their romance blossomed in the late 1990s, and they dated publicly from 1999 to 2002. Their breakup was highly publicized, with speculation that Timberlake’s hit song 'Cry Me a River' was inspired by their split.