Denise Richards and Charlie Sheen, 2005
This celebrity split may take the cake: restraining orders, death threats, substance abuse, prostitution, porn ... the list goes on. On the one hand, you want to feel bad for Denise Richards. When she filed for divorce from Charlie Sheen, she was six months pregnant with the couple's second child. She told a crazy tale of Sheen's alleged addictions to gambling, drugs, prostitution and pornography and claimed he was abusive. But on the other hand, you want to say to her, "You know you married Charlie Sheen, right?" While Sheen denied the allegations, calling them a "smear campaign," the Two and a Half Men star is no stranger to trouble — he had previously been accused of roughing up girlfriends, hiring hookers and abusing drugs. Their hostile divorce and custody battle raged for years in one of the ugliest court battles Hollywood has ever witnessed.