Howard Stern, the brash, rule-bending "shock jock," has been the voice of unfiltered radio since the 1980s. "The Howard Stern Show" was nationally syndicated on terrestrial radio from 1986 to 2005. In 2006, he took a plunge into the less-restrictive satellite format. Stern, nicknamed "The King of All Media," has a staggering net worth of over $600 million. On top of being one of the most successful radio personalities of all time, he is also the most fined, thanks to the FCC, which issued him penalties worth over $2.5 million dollars. His on-air tenure has been incredibly lengthy, but incredibly tenuous. Take a look back at some of the craziest points of his career.

(Dan Gunderman)