In one typical example of his radio show, he persuaded a female caller to have phone sex with him on the air. He made deep buzzing noises into his microphone, and had her sit on a speaker with the volume turned up until she reached an on-the-air orgasm. Another notable episode was on WWDC-FM (DC101 Radio) in Washington D.C. in which Stern called Air Florida and asked what the fare was for a one-way ticket from Washington National Airport to the 14th Street Bridge (on the Potomac River less than 1 mile from the airport). He was making light of the crash of Air Florida Flight 90 one day earlier, on January 13, 1982, which had killed 78 persons (both onboard the airplane and in vehicles stopped in traffic on the bridge). That June 29, Stern was fired from DC-101 radio after being suspended for criticizing his station management and two other radio stations. Stern's lawyer alleged, "It's our view that the real reason they've [fired Stern] is they would like to get new DC-101 deejays "GreaseMan" and "Adam Smasher" on the air as soon as possible, and hope the audience forgets about Howard, and that's a perfectly rational business judgment."

Stern has also shown the ability to take society's misfits and turn them into celebrities through The Wack Pack. Wack Pack members are able to parlay their exposure on Stern's show into personal appearances at clubs and even the occasional movie.

Stern has referred to himself as the "King Of All Media," a parody of Michael Jackson's claiming of the title "King of Pop." To his subjects this title is true, as they have been loyal consumers of The King's books, pay-per-view events and movies. Stern believes he represents the future of America, where, in keeping with a longstanding trend, public moral standards will continue to loosen. His show was frequently the subject of complaints by various listeners who find his deliveries offensive - something he deliberately encourages. Fines were occasionally issued against radio stations airing his show, generally for violating FCC requirements regarding content. Still, the parent conglomerate that hosted Stern's show, Infinity Broadcasting (a subsidiary of Viacom), seemed to consider those fines a necessary price to pay in order to support Stern's continuing popularity.

As of November 2004, the show, typically airing in the morning, was syndicated on 45 radio stations all across the U.S. (27 owned by Infinity Broadcasting), down from Stern's peak syndication of 62 stations. Those stations were not allowed to stream the show over the internet.

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The Howard Stern Show debuted on Sirius, on January 9, 2006. The "Howard 100 Heartbeat" broke away to Also Sprach Zarathustra tunefully performed with flatulence. Howard's theme music, "Great American Nightmare," played a few bars before George Takei introduced himself as the show's new announcer. Callers were soon invited to call into the show using their new toll-free line, 1-888-9-ASSHOLE.

During the show, Stern revealed that there were 180,000 Sirius receivers activated the day before his inaugural broadcast. He also revealed that he was not married, squashing rumors which appeared (and he happily fed) during his hiatus. One of his first radio acts on Sirius included the uncensored Pat O'Brien sex tapes and his uncensored version of parody songs using the sex tape.

To dispel the notion that the move to Sirius would unleash a wave of cursing and vulgar language, Stern placed a gag order on himself and other members of his staff. Sal the Stockbroker and Ronnie the Limo Driver were especially singled out for excessive cursing and have since been forbidden to curse. Although Stern has the occasional guest slip up, such as when Alexis Stewart recalled a friend describing her as "cunty," he has been conscious of not overdoing it. However, he has given Artie Lange carte blanche to use whatever language he wants, stating that "when Artie curses, it's funny."

In addition to his regular morning show, which is replayed at 1pm est, 7pm est and 1am est during the week on Howard 100, several "spin-off" shows have emerged, such as The Wrap Up Show, The Super Fan Rountable, and The Intern Show, all dedicated to discussion of the Stern Show from the points of view of Howard's producer, fans and interns, respectively.

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On April 28, 2006 the first Annual Howard Stern Film Festival debuted at The Hudson Theatre in New York City. The film festival took entries from fans and featured a grand prize of $35,000 in cash and prizes. Stern said of the festival, "People want access. The Tribeca Film Festival is too commercial. This is the one where the next great comedy directors will be discovered. This is good for New York, and it's good for the listeners. They get to come down here, participate, make creative films, and all the films are about me. What better topic is there?"

The winner of the festival was Scott Masterson whose film "Radio Play" was a sentimental tribute to Stern that wondered what it would be like if Stern, Quivers, and Norris met over HAM Radio as children.

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