Angelina Jolie and Billy Bob Thornton
Before the media frenzy of Brangelina, Angelina Jolie was married to actor and musician Billy Bob Thornton. Their romance shocked many, not only due to the 20-year age difference but also because of their passionate, eccentric dynamic. The pair met while filming a movie and were married from 2000 to 2002, known for their public displays of affection and even wearing vials of each other’s blood.
What many don’t realize is that Angelina was Thornton’s fifth wife. Although the couple ultimately parted ways, Billy Bob later shared that their different lifestyles made long-term harmony difficult. Still, there’s no bitterness between them—Thornton has spoken warmly about their time together, and the two remain on friendly terms. Their whirlwind marriage may have burned fast and bright, but it left behind mutual respect and some unforgettable tabloid moments.