On his first date with Alison, his wife of 21 years, saw a film based on the life of Lenny Bruce, an embattled entertainer whose career he would match for controversy over censorship
Cost Infinity Broadcasting and Clear Channel Communications at least $4 million in FCC fines for indecent content from his 20-year nationally syndicated radio show that originated from WXRK (K-ROCK) in New York City
Launched Howard Stern on E! in 1993, the most durable small-screen project of the many attempted by the self-proclaimed "King of All Media
" Set an earnings record for non-sports pay-per-view programming when the 1993-94 Miss Howard Stern New Year's Eve Pageant grossed $40 million
Briefly ran for Governor of New York on the Libertarian ticket in 1994, dropping out before the election when told he was required to disclose personal finances
Played himself in the 1997 Betty Thomas-directed Private Parts, which also featured his radio cohorts Robin Quivers and Fred Norris
Produced Son of the Beach, a raunchy, campy FX series about a loopy lifeguard
Removed the burden of censorship by signing a $500 million, five-year deal with Sirius satellite radio, where, in his second week, he admitted to having plastic surgery on his nose and chin in 1997
His 2008 wedding to Beth Ostrosky was officiated by actor Mark Consuelos, who is also an ordained minister