It aired weekly on Saturday nights from July 14, 1990, to August 1, 1992, from WWOR-TV in Secaucus, New Jersey, and was nationally syndicated by All American Television from 1991.

By 1990, Stern had been the host of his morning radio show on WXRK in New York City for almost four years, and was also simulcast on stations in Philadelphia and Washington, D.C.

[1] Stern went on to reach success in the pay-per-view and home video markets with his Negligee and Underpants Party and U.S. Open Sores specials in 1988 and 1989, respectively.

[2][3] Woodruff was keen on Stern in order to "beat the boredom of summer reruns" that WWOR-TV aired, and that his "provocative commentary should make funny television.

[3] The show generated controversy before it started to air, when WWOR-TV received calls from several people asking which sponsors had bought advertising time on the program, so they could write letters of protest to the companies.

The station's publicity manager noted that the attention generated from the protests had the potential to in fact boost the program's ratings, and Woodruff said the criticisms against Stern and the television show were unfair as it had yet to air.

[8] On January 10, 1991, the program entered national syndication by All American Television, with alternate content replacing the live commercial reads which aired on WWOR and were targeted to the New York City market exclusively.

[13] In the New York market, The Howard Stern Show often doubled the ratings share of Saturday Night Live on NBC during the half-hour the two programs overlapped.