He discovered a talent for Lenny Bruce-type comedy, and developed a wide-ranging confrontational style that encouraged listeners to call in. Eventually, in the 1990s, his show was widely distributed.
As an example, in one of his most infamous episodes, he persuaded a female caller to have sex with him on the air, over the telephone. 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 infamous episode was on DC101 Radio in Washington D.C. in which Stern called Air Florida Airlines and asked what the fare was for a one-way ticket from National Airport to the 14th Street Bridge. He was making light of the crash of an Air Florida flight into the 14th Street Bridge in Washington D.C. one-day earlier and as a result of this bit he was fired by DC101.

Howard Stern's rude and crude style of entertainment (which many listeners support nonetheless) has earned him the sobriquet of shock jock and the title King Of All Media -- at least in the eyes of his fans. In his own mind Stern represents the future, where public moral standards will be much lower than now, in keeping with a longstanding trend. His show is frequently the subject of complaints by various listeners (and occasionally ethnic groups) who find his deliveries offensive - which he goes out of his way to encourage. Radio stations airing his show have occasionally been subjected to fines for violating FCC requirements due to the content of the show, but the parent conglomerate (Infinity Broadcasting, a subsidiary of Viacom) that hosts Stern's show seems to consider these fines a necessary price to pay, in order to support Stern's continuing popularity.

In 1992 the FCC fined Infinity Broadcasting $600,000 after Stern discussed masturbating to a picture of Aunt Jemima. His April 21, 1999 show drew angry criticism for his comment regarding the motives of the two male students who murdered 12 classmates and one teacher in the Columbine High School massacre in Colorado: "There were some really good-looking girls running out with their hands over their heads. Did those kids try to have sex with any of the good-looking girls? They didn't even do that? At least if you're going to kill yourself and kill all the kids, why wouldn't you have some sex? If I was going to kill some people, I'd take them out with sex."

In 1994 Stern embarked on a political campaign for Governor of the state of New York formally announcing his candidacy under the Libertarian Party ticket. Although he fulfilled the necessary requirements and ran a legally authorized campaign, most outside observers saw his run for office as little more than a publicity stunt.

In spite of the crude content of his show, many radio listeners consider Stern's delivery to be far from the worst quality radio aired today. His popularity has given rise to a number of imitation shock jocks who attempt to outdo Stern in terms of offensiveness and rudeness, but these imitators have found themselves with more troubles to worry about than listener ratings. In 2002 fellow Infinity Broadcasting Corporation jocks Opie and Anthony had their nationally syndicated WNEW-FM extreme talk show cancelled after they encouraged a couple to engage in sexual intercourse at Saint Patrick's Cathedral in New York City, then airing a running commentary of the act on their show. Stern, his supporters note, has not gone out of his way to offend the general public in this manner.

The number of commercials aired during his radio show has greatly increased from the 1980s to the present.

In 1997 Stern's loosely autobiographical book, Private Parts, was adapted to film. The movie did well at box offices and in video release, garnering a total of over $60 million. His next movie, still in the works, is The Adventures of Fartman.

Being one of those personalities that people either love or hate, but nobody is neutral about, he has had his share of stalkers and death threats. On January 15, 1998 Lance Carvin, who had been stalking Stern, was sentenced to two and a half years in prison for threatening to kill Stern and his family.