7. Billy Bob Thornton
These days, Billy Bob is best known as the former half of the Angelina Jolie marriage, where the had the sick practice of wearing each other’s vials of blood around their necks. But that blood pact didn’t work either. And so his marriage to Angelina Jolie was his fifth, and it ended the same as the four before it — in divorce — in 2003. But, at least he got to make love to Halle Berry on-screen.