Everyone remember’s Sheen’s drug-and-porn-star rampage a few years ago, but the actor’s run-ins with addiction and legal problems date farther back than that. In 1990, Sheen accidentally shot Kelly Preston, his then-fiancee, in the arm. Needless to say, she called the wedding off. Even his partying a few years ago wasn’t just harmless fun, as the actor faced charges in 2009 of assaulting his wife, Brooke Bueller. In 2010, he was removed from a hotel suite after doing seven grand in damages. And of course, back in 1998, Sheen overdosed on cocaine and was sent to rehab (which didn’t seem to stick). We could go on, but we’ve still got two more to go on this list.