Howard Stern | $21 Million, New York | Chevrolet Corvette

Howard Stern is probably the most famous radio personality in America. His radio show The Howard Stern Show has been around since 1986. In 2006, it moved to another broadcast network, SiriusXM Satellite Radio, for which he signed a $500 million contract. To his credit, the self-proclaimed King of Media has also achieved success outside the world of radio broadcasting. He had his stint as a judge in the famous talent show, America’s Got Talent. Moreover, Howard has two New York Times Best Seller books, Miss America and Private Parts.

With all the wealth The King of Media has earned, you wonder what he does with it. Buy a string of luxurious properties and cars, of course. Well, not so much fancy cars. In one of his books, Howard shared his bad experience with sports cars. He fondly recalls the time he bought a Corvette convertible and how he found himself looking like a Big Bird float. Putting luxury vehicles aside, he has several properties, all worth millions. One of which is his penthouse in Manhattan worth $21 million. The combined five condominiums is a lavish 8,000-square-foot pad that he purchased in over a decade.