Howard Stern

The self-dubbed King of All Media earned millions of fans — not to mention dollars — channeling his id across the airwaves. Born in Long Island, this gawky nerd didn't look like a star, which made radio a perfect career move. After trying to conform to the medium's conventions — and failing — Stern took a shot at being "himself" (or a prurient version thereof) and the gamble paid off. When his morning show was syndicated nationally in the mid-'80s, the shock jock became an unstoppable machine. Still, he frequently drew criticism (sometimes from his own long-suffering wife, Alison) as well as FCC fines for outrageous antics like Homeless Hollywood Squares and Butt Bongo. Soon A-list celebrities — as well as attractive young women willing to disrobe — were clamoring to get on the show, even though Stern would inevitably put them through the wringer. Listeners ate it up in large part because they identified with Stern's shtick as a sexually frustrated married man. In the '90s he branched out into other media, hosting several TV shows; writing an autobiography, Private Parts; starring in the book's film adaptation; and producing various specials and series. Then in 1999 Stern surprised his fans by announcing that he and his wife of 21 years were splitting. But the show went on and was as popular (and controversial) as ever. In 2004, fed up with the constant battles with censors, Stern announced that he would ditch the terrestrial radio for satellite starting in 2006, signing an unprecedented $500 million, five-year deal with Sirius.