Angelina Jolie
This was a real heartbreaker! Their chemistry blossomed during the production of Mr. & Mrs. Smith in 2004. Brad was still married to Jennifer Aniston at the time. Pitt and Aniston divorced in 2005, and “Brangelina” was born a year later, with a kid on board. In 2016, Brad and Angelina will call it quits on their relationship.
Angelina Jolie
Britney Spears
In 2004, the pop diva began dating backup dancer Kevin Federline, and the two became engaged after three months of dating. But there was one minor snag: Federline was already married to Shar Jackson. Not only that, but Shar was also expecting her second child with Federline at the time. Despite this, Spears and Federline married a few months later and had two sons together. In 2006, Britney Spears and Kevin Federline divorced.
Britney Spears
