HOWARD STERN—EST. $650 Million

Howard Stern, born in New York on January 12, 1954, is an American screenwriter, producer, actor and director. He once wrote in the book that he suffered from obsessive-compulsive disorder and was under active treatment. He’s dubbed himself the “King of all Media,” and while we don’t necessarily agree with that moniker, we have to give it to the man for popularizing the term shock jock, with his controversial personality and morally questionable radio show practices.

Not everyone likes the man’s style—he definitely had his iffy moments—but he’s been able to carve a niche for himself in the radio industry, and we suppose enough people do in fact like him, which is why he is as rich as he is. The man is no stranger to lawsuits, having been involved with quite a few. He’s lucky that he has $650 million to spend on a lawyer if he needs one.