The Ex: Britney Spears
When two of pop's biggest stars break up, there's only one real way to handle it: with a song. Timberlake's 2002 hit "Cry Me a River," thought to be a jab at Spears – who's seemingly accused of cheating in the music video – brings the waterworks in the form of a cool, catchy ballad. "You told me you loved me/Why do you leave me/All alone," the recently married man sings in the song, which was, tellingly, later covered by both Justin Bieber and Selena Gomez.