Remember how we said you can make a lot of money by courting controversy? Howard Stern has taken that ball and run it for miles. Stern is the man that the term 'shock jock' was invented for, and the outrageous content of his radio talk shows have made him a very rich man despite all the fines he'd had to pay because of it.
Capitalizing on his notoriety, he wrote a mostly autobiographical book called 'Private Parts' which went on to be a best seller, and when the novel was adapted into the film, Stern insisted on playing the lead role himself, which earned him yet another huge paycheck just for basically being himself. He also very nearly became Governor of New York, in the 90s, comfortably winning the first ballot, but withdrew from the race when it became clear he'd be required to provide details about his private life which he didn't want to give.