At the age of 11, Stern moved to Roosevelt, Long Island, New York, the United States. His father has worked in the U.S. Army in Long Island and California during the war whereas his mother was an office clerk. Stern joined Washington-Rose Elementary School and he also attended Roosevelt Junior-Senior High School for his education. He also completed his Communications degree from Elmira College at Boston University.
During his early five, Stern was interested in being a radio and television host. He started working as a radio host while he was at Boston University. He came into the limelight via morning shows at WRNW in Briarcliff Manor, New York, WWWW in Detroit, Michigan, WCCC in Hartford, Connecticut, and WWDC in Washington, D.C.
Stern also served for afternoons show at WNBC in New York City before he was fired in 1985. Later, he started working at WXRK in New York City and his morning show entered syndication. His show also aired in 60 markets and attracted 20 million listeners at its peak. He has also worked as a judge on America's Got Talent.
Stern is an American by nationality and belongs to white ethnicity; he married twice in his life. He married his longtime girlfriend, Alison Stern, at the Temple Ohabei Shalom in Brookline, Massachusetts. The couple first met at Boston University. The couple blessed with three children Emily Beth, Debra Jennifer, and Ashely Jade. However, he was unable to continue his married life with his wife and divorced her.
After divorcing his first spouse, he married his second wife, Beth Ostrosky, after dating her for sometimes. In the past, he had affairs with Angie Everhart and Robin Givens.
As a radio and television personality, Stern earns a huge amount of money from his professional career. He made a five-year-contract with Sirius, worth around $500 million and became the highest-paid radio personality. His current net worth is estimated to be $645 million and for his appearance in different shows, he receives an annual salary of around $90 million.
His two books Private Parts (1993) and Miss America (1995) grossed $41.2 million domestically in a week and also entered The New York Times Best Seller list at number one and sold over one million copies.