Howard Allan Stern was born to Ben and Ray Stern on January 12, 1954. He has one sister, Ellen. He grew up in Roosevelt, Long Island, and frequently references his upbringing as a Jewish kid trying to fit in with his fellow students. Stern was introduced to the radio business early on when he went to work with his dad, who owned a recording studio. Stern earned his bachelor's degree in communications from Boston University in 1976. In 1978, he married Alison, whom he'd met in college.

Stern's first morning show job was in Hartford, CT, at WCCC, where he met future collaborator and producer Fred Norris. Stern's next moves were to Detroit, Washington, D.C., and finally New York City, where he worked for WNBC Radio. Along with developing his radio career, Stern was busy discovering his own style of entertaining listeners. His honesty and penchant for sexual content made for an interesting and Federal Communications Commission (FCC) fine-inducing style. His official battles with the FCC started with his first fine on December 16, 1988, totaling 6,000 dollars. Ten fines and 16 years later, his last fine reached 3.5 million dollars.

Stern dubbed himself the "King of All Media" after he successfully ran television shows and wrote a book, Private Parts, in 1997. It was turned into a movie in 1998 under the direction of Betty Thomas. Stern regulars re-created his rise to fame, and future awards stalwart Paul Giamatti starred as WNBC executive Kenny "Pig Vomit" Rushton. Stern also served as executive producer to the short-lived FX comedy Son of the Beach in 2000.

Along with Norris, Stern's on-air entourage included Jackie Martling, John Melendez, lone female Robin Quivers, and a revolving group of characters called The Wack Pack, ranging from late actor Matthew McGrory (aka "Bigfoot") and Hank the Angry Drunken Dwarf (also deceased). In March 2001, Martling left the show after contract talks didn't result in his desired salary; later that year, comedian Artie Lange replaced him. Martling returned to Stern's satellite show to talk about why he left and ended up hosting his own weekly comedy show, Jackie's Joke Hunt. Melendez jumped the Stern ship in 2004 to become the announcer on The Tonight Show.

Proof of Stern's dedication as a broadcaster came on September 11, 2001, when he and his staff stayed on the air throughout the attacks. Friends of the show called in with eyewitness reports of what was going on and Stern stayed on well after his time slot had ended.

Racking up fines, regular guests, and enemies, Stern also built a big enough fan base to make the jump from terrestrial to satellite radio in 2005. His first censorship-free show aired on Sirius channels 100 and 101 on January 9, 2006; his 500-million-dollar contract covered five years.