Angelina and Billy Bob Thornton (2000-02)

Eloping in Las Vegas? Red flag. Eloping in Las Vegas with someone almost twice your age (Jolie was 24, Thornton was 44) after two months of courtship? Double red flag. Coined America's most dangerous marriage by Rolling Stone, the two were known not only for their vomit-inducing displays of passion in public but also for wearing each other's blood in vials around their necks. (We're going to go out on a limb and call another red flag.) Thornton even said in an interview with Entertainment Tonight, "I wear her underwear a lot when we're away. And she wears mine." To amp up the romance, Jolie gave Thornton a grave plot for their anniversary. Sadly, Thornton's disgusting soul patch has endured the test of time, but the marriage did not, falling apart after two years.
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