Angelina Jolie: The Beginning
Years Together: 2000-2003
Duration: 3 years
Billy Bob Thornton and Angelina Jolie’s relationship began in 1999 while they were filming Pushing Tin. Thornton was in a relationship with Laura Dern at the time, but his intense connection with Jolie quickly turned romantic.

The couple’s whirlwind romance shocked Hollywood, especially when they eloped in 2000, just months after Thornton ended things with Dern. Their relationship made headlines for its passionate and eccentric nature. The couple often talked about their deep, almost spiritual connection and famously wore vials of each other’s blood as a symbol of their love.