[1] Stern began his radio career in the mid-1970s and developed his show through morning positions at WRNW in Briarcliff Manor, New York, WCCC-FM in Hartford, Connecticut, and WWWW in Detroit.

Stern landed his first professional radio job while at Boston University, performing on-air skits, news casting and production duties at 1550 WNTN in Newton, Massachusetts, from August to December 1975.

[2] He also hosted a show with three fellow students on WTBU, campus radio station, named The King Schmaltz Bagel Hour which was cancelled during its first broadcast for a sketch called "Godzilla Goes to Harlem".

[3] After his graduation, Stern landed some cover shifts in December 1976 at WRNW, a progressive rock station in Briarcliff Manor, New York, where he was subsequently hired full-time working middays.

"[4] In 1979, Stern responded to an advertisement for a "wild, fun morning guy" at WCCC-FM, an album oriented rock (AOR) station in Hartford, Connecticut.

Stern held a bra-burning event and wrestled women outside the studios, and invited listeners to confess the most outrageous places where they had sex, and record their calls for the air.

[11][12] A stunt in which listeners paid $1.06 (the station's FM frequency) to hit a Japanese car with a sledgehammer earned Stern national mention.

For his performance, Stern won a Billboard award for "Best Album-Oriented Rock Disc Jockey" and was featured in the Drake-Chenault "Top Five Talent Search" contest in the AOR category.

[13] Published in January 1981, the fall Arbitron ratings showed that Stern trailed his three rock competitors with a 1.6% market share of the listening audience during an average quarter-hour.

On March 2, 1981, Stern began his third morning job, this time at WWDC-FM, a rock station in Washington, D.C.[10] He was determined to become a success, and noticed the importance of news segments for satire.

[19] He formed the Think Tank, a cohesive trio of male listeners who conversed with Stern and played along with quizzes and routines, which helped the show sound more natural.

[30] Martling assumed his role full-time in August 1986 when he replaced Al Rosenberg, a comedian and writer at WNBC who could no longer commute from Washington, D.C.[14] Also hired was Gary Dell'Abate of the station's traffic department, who started as the show's assistant in September 1984 and went on to become executive producer.

He had a naked woman on the show for the first time and attempted to make another reach orgasm through her radio speaker, both of which were reenacted in his film Private Parts (1997).

"[34] In 1992, Stern believed that Thornton Bradshaw, at the time chairman of RCA which then owned WNBC, was driving in his limousine having heard his "Bestiality Dial-a-Date" segment and ordered his firing.

[29] Later, NBC chairman Grant Tinker admitted that it was his decision, after corporate communications director Bob Rukeyser alerted him about the risqué material on Stern's show.

[41] Between September 1986 and February 1987, Stern hosted a three-hour Saturday morning program with a live audience which was syndicated to 45 markets across the country by DIR Broadcasting.

[41] The show added two new staff in 1988—impressionist Billy West and intern "Stuttering John" Melendez, who would achieve notoriety by asking celebrities awkward questions on the red carpet and press conferences.

[63][65] Justice of the Peace Eloy Cano of Harlingen, Texas, issued an arrest warrant on Stern for disorderly conduct,[66] which remained in place for a year after the incident.

[79] A day after the Columbine High School massacre in Littleton, Colorado, on April 20, 1999, Stern's comments regarding the incident drew criticism from some listeners.

[85] Industry analysts questioned Stern's relevance as the show's ratings had declined since 1998, including a 20 per cent drop in listeners in Los Angeles.

[89] In September 2003, the FCC declared the show a "bona fide news interview program", making it exempt from equal-time requirements placed for political candidates.

Stern accused Leno of stealing his segments such as goofy red carpet interviews and booking Kenneth Keith Kallenbach, a member of the show's Wack Pack.

On February 26, 2004, Stern was cancelled on six stations owned by Clear Channel Communications after a caller used the word "nigger" when asking Rick Salomon if he ever had sex with a black person the day before.

A contributing factor in the decision was the aftermath of the Super Bowl XXXVIII halftime show controversy which began the tightening of censorship and regulation in broadcasting.

In his closing speech, Stern thanked the New York City Police Department, dedicating the show to Sergeant Keith Manning, a friend who at the time was serving in Iraq.

[108] Stern was replaced with The Adam Carolla Show on numerous West Coast affiliates, and the still airing Rover's Morning Glory in mostly Midwestern markets.

"[113] Stern announced on June 7, 2006, that the lawsuit settlement with CBS Radio finally gave Sirius the exclusive rights to his entire back catalog of broadcasts from WXRK, totalling almost 23,000 hours.

The New York Times wrote: "Scattered among the gleefully vulgar mainstays are now long, starkly intimate live exchanges—character excavations that have made Mr. Stern one of the most deft and engrossing celebrity interviewers in the business and a sought-after stop for stars selling a movie or setting the record straight.

[129] From 1990 to 2004, the Federal Communications Commission (FCC) fined owners of radio stations that carried The Howard Stern Show a total of $2.5 million for indecent programming.

The Wack Pack is a group of people featured on the show, each of whom bears a signature trait, such as a skill, disability, or a unique personal appearance.