2001: Justin Timberlake and Britney Spears

The Justin Timberlake and Britney Spears tandem generated quite a lot of buzz in the music scene as these two were at the peak of their careers at the time. The two worked together in The All-New Mickey Mouse Club and reconnected during the 90s. They later became an item, much to the delight of their fans, but things didn’t work out so well. In 2002, the couple separated, and rumors of cheating were circulating.

Spears denied that she was seeing someone else while she was with Timberlake, and stated that it was Timberlake who did not want to get married. Though no one revealed why they broke up, Timberlake recently apologized to his ex. Hopefully, Spears can get a good financial advisor to help her with her earnings as a musician because her money has been the subject of a long legal battle with her father.