2. Charlie Sheen
Charlie Sheen’s drug-filled rants, his infamous engagement to a former adult entertainment actor, and his wild behavior that had him fired from Two and a Half Men all lead up to him being a lunatic who remains successful in Hollywood. It’s crazy to think that despite having such a negative reputation on him, Charlie is still one of the richest men in Hollywood, having made $1 million per episode on the former CBS show. He has since moved on to other businesses, which see him make an estimated $9 million a year, which is still a lot, to say the least.