Stern landed his first radio jobs while at Boston University. From 1976 to 1982, Stern 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 worked afternoons at WNBC in New York City from 1982 until his firing in 1985. In 1985, he began a 20-year run at WXRK in New York City; his morning show entered syndication in 1986 and aired in 60 markets and attracted 20 million listeners at its peak. Stern won numerous industry awards, including Billboard’s Nationally Syndicated Air Personality of the Year eight consecutive times, and is the first to have the number one morning show in New York City and Los Angeles simultaneously. He became the most fined radio host when the Federal Communications Commission issued fines totaling $2.5 million to station owners for content it deemed indecent. Stern became one of the highest paid radio figures after signing a five-year deal with Sirius in 2004 worth $500 million. In recent years, Stern's photography has been featured in Hamptons and WHIRL magazines. From 2012 to 2015, he served as a judge on America's Got Talent.

Stern has described himself as the "King of All Media" since 1992 for his successes outside radio. He hosted and produced numerous late night television shows, pay-per-view events, and home videos. Two of his books, Private Parts (1993) and Miss America (1995), entered The New York Times Best Seller list at number one and sold over one million copies. The former was made into a biographical comedy film in 1997 that had Stern and his radio show staff star as themselves. It topped the US box office in its opening week and grossed $41.2 million domestically. Stern performs on its soundtrack, which charted the Billboard 200 at number one and was certified platinum for one million copies sold. Stern's third book, Howard Stern Comes Again, was released in 2019.