Britney Spears and Justin Timberlake

In the early 2000s, there was no couple more closely followed than Britney Spears and Justin Timberlake, a pair made in pop star heaven. The two met as children on the set of the Mickey Mouse Club and started dating in their teens. They came to a messy end when Spears reportedly cheated on Justin with a choreographer, a subject explored in his "Cry Me a River" video.