The Hook Up: The St. Louis rapper and the R&B starlet met at the MTV Video Music Awards in 2003 and started dating secretly shortly afterwards.
The Break Up: Amidst reports of Nelly cheating, the hip-hop power couple split sometime during the summer of 2009. But they revealed very little about their relationship publicly.
The Mess They Left: You could make the argument that both former superstars saw their stock plummet in the music industry as a result of their relationship. Because neither of them acknowledged much about their personal life, they've both been off the scene for a few years now.