From 1976 to 1982, he developed his on-air personality through morning positions at WRNW in Briarcliff Manor, New York; WCCC in Hartford, Connecticut; WWWW in Detroit, Michigan; and WWDC in Washington, D.C.

Stern has won numerous industry awards, including Billboard's Nationally Syndicated Air Personality of the Year eight consecutive times, and he is the first to have the number one morning show in New York City and Los Angeles simultaneously.

[15][17] His father set up a microphone, tape machine, and turntable in the basement of his home, which Stern used to record his make-believe radio shows, incorporating different characters and pre-recorded prank calls, sketches, and commercials.

[21] In June 1969, the family moved to nearby Rockville Centre, and Stern, at age fifteen, transferred to South Side High School where he became "a total introvert.

[29][30] With the license, Stern landed his first professional radio job at WNTN in Newton, Massachusetts from August to December 1975 doing air shifts, news casting, and production work.

[33] Stern accepted a marketing role at Benton & Bowles, a New York advertising agency, which he soon "quit without giving notice" in favor of a position in the creative department.

[37] He used some morning airtime to assemble an aircheck with more outrageous bits, including Robert Klein and Cheech and Chong records with added flatulence routines and one-liners.

He also completed duties as the station's public affairs director and hosted a Sunday morning talk show that he favored above playing records,[39] as it "represented what I wanted to do on the radio more than anything.

The quarterly Arbitron ratings released in January 1981 showed no signs of a strong audience, causing the station to change formats overnight from rock to country music, to Stern's surprise and annoyance.

[52] During his time relocating from Detroit, Stern spent several weeks planning out a new show, determined to become more successful as the station presented a good chance for him to work in New York City, his career goal.

[62] In his last few months, Stern secured a $35,000 advance deal with Wren Records to produce a comedy album of song parodies with Norris, titled 50 Ways to Rank Your Mother.

In April 1982, four months before he started at WNBC, NBC Magazine aired a critical news report on shock radio by Douglas Kiker that centered around Stern and the controversial nature of his show.

In 1992, he believed Thornton Bradshaw, chairman of WNBC owner RCA, heard his "Bestiality Dial-a-Date" segment that aired ten days before his suspension and ordered the show's cancellation.

[36] In a press conference held in October 1985, Stern announced the signing of a five-year contract with Infinity Broadcasting worth an estimated $500,000[76] to host afternoons on its rock music station WXRK from November 18.

Following discussions with the network that began in late 1986,[83] Stern agreed to five one-hour pilots that were produced for an estimated $400,000, with guitarist Leslie West as his band leader and comedian Steve Rossi as the show's announcer.

[96] Development for The Adventures of Fartman, a feature film based around the character, began in late 1992 with Stern reaching a verbal agreement with New Line Cinema to release it.

[1] Stern planned to reinstate the death penalty, remove highway tolls to improve traffic flow and limit road work to graveyard shifts hours.

[119] Stern withdrew his candidacy in an on-air press conference two days later, saying: "I spend 25 hours a week telling you all the most intimate details of my life ... One fact I've never revealed is how much I make and how much money I have ... it's none of your business".

[126] After three days of widespread media reaction and boycott threats, Stern responded with a statement in Spanish, stressing his comments were made in satire and were not intended to hurt those who loved her.

[127] The next day, Eloy Cano, a Justice of the Peace of Harlingen, Texas, issued an arrest warrant on Stern for disorderly conduct that carried a potential maximum fine of $500 if he entered the state.

[130] Stern wrote about various topics, including his cybersex experiences on the Internet service Prodigy, a private meeting with Michael Jackson, his suffering with back pain and obsessive–compulsive disorder, and his run for Governor of New York.

[137] Stern embarked on an extensive publicity tour to promote the film which included numerous television appearances and magazine interviews in his attempt to appeal to people who were not listeners of his radio show.

Private Parts premiered on February 27, 1997, at The Theater at Madison Square Garden; outside the theatre, Stern and Rob Zombie performed "The Great American Nightmare", a track they recorded for its soundtrack.

In September 1999, the UPN network announced the production of Doomsday, an animated science-fiction comedy television series, for an initial thirteen episodes originally set to air in 2000.

The series was described as: "Set in a post-apocalyptic America nearly destroyed by a freak radiation burst, [the show] follows the travels of the Bradley family as they cross the country in an RV looking for a new place to call home".

[157] Stern spoke at The Concert for New York City in October 2001 in a hazmat suit with his buttocks exposed similarly to his 1992 MTV Music Video Awards appearance.

[168] Stern also worked on a pilot with Robert Schimmel for The WB, based around the comedian's real-life experience of falling in love with his daughter's best friend following his battle with cancer, but was not picked up.

[169] The controversy surrounding the Super Bowl XXXVIII halftime show, aired live on February 1, 2004, led to the government's crackdown on indecency in radio and television following a surge in audience complaints.

[206] In February 2015, Whalerock Industries announced its partnership with Stern to set up a future direct-to-consumer digital "media hub" service, with a potential mix of free and subscription-based programming.

[220] Between 1990 and 2004, the Federal Communications Commission (FCC) fined owners of radio station licensees that carried The Howard Stern Show a total of $2.5 million for content it considered to be indecent.