Billy Bob Thornton and Angelina Jolie
In 2000, Laura Dern had the heart of every Hollywood fan. The beautiful girl caught everyone’s attention. Unfortunately, her Oscar-winning co-star Billy Bob Thornton decided she was no longer worth working with her. His feelings for her waned when he was producing Pushing Tin and falling in love with Angelina Jolie. After getting engaged to Laura, Bob ended the relationship to marry Jolie. After being together for three years, they decided to separate. At one point, they even exchanged underpants in public, just one of the many strange things they did that got them attention from the press.