CelebritiesPosted byThe List
As many Angelina Jolie fans know, she was a bit wild in the 1990s, especially when it came to her second husband, Billy Bob Thornton. They met on the set of "Pushing Tin" in 1999, and little did they know they'd be tying the knot months later. In 2000, Thornton was engaged to fellow actress, Laura Dern, and Jolie was paired with Timothy Hutton. In May, the couple booked an appointment with a minister in L.A., who helped them to make their marriage official (via MSN). At the time they hooked up, she was 24 and he was 20 years her senior, according to WhosDatedWho.