Hefner was born in Chicago, Illinois, the oldest of two sons born to Grace Caroline (née Swanson; 18951997) and Glenn Lucius Hefner (18961976), both teachers. Hefner's mother was of Swedish descent and his father had German and English ancestry. On his father's side, Hefner claims he is a direct descendant of Plymouth governor William Bradford. He has described his family as "conservative, Midwest, Methodist." He went to Sayre Elementary School and Steinmetz High School, then served as a writer for a military newspaper in the U.S. Army from 1944 to 1946. He later graduated from the University of Illinois at Urbana Champaign with a B.A. in psychology with a double minor in creative writing and art in 1949, earning his degree in two and a half years. After graduation, he took a semester of graduate courses in sociology at Northwestern University but dropped out soon after.
Working as a copywriter for Esquire, he left in January 1952 after being denied a $5 raise. In 1953, he mortgaged his furniture, generating a bank loan of $600 (or $800 — he cannot recall which) and raised $8,000 from 45 investors — including $1,000 from his mother ("Not because she believed in the venture," he told E! in 2006, "but because she believed in her son.") — to launch Playboy, which was initially going to be called Stag Party. The undated first issue, published in December 1953, featured Marilyn Monroe from her 1949 nude calendar shoot and sold over 50,000 copies. (Hefner, who never met Monroe, bought the crypt next to hers at the Westwood Village Memorial Park Cemetery.)
After it was rejected by Esquire magazine in 1955, Hefner agreed to publish in Playboy the Charles Beaumont science fiction short story, "The Crooked Man", about straight men being persecuted in a world where homosexuality was the norm. After receiving angry letters to the magazine, Hefner wrote a response to criticism where he said, "If it was wrong to persecute heterosexuals in a homosexual society then the reverse was wrong, too.
On June 4, 1963, Hefner was arrested for selling obscene literature after an issue of Playboy featuring nude shots of Jayne Mansfield was released. A jury was unable to reach a verdict.
His former secretary, Bobbie Arnstein, was found dead in a Chicago hotel room after an overdose of drugs in January 1975. Hefner called a press conference to allege that she had been driven to suicide by narcotics agents and federal officers. Hefner further claimed the government was out to get him because of Playboy's philosophy and its advocacy of more liberal drug laws.
He has a star on the Hollywood Walk of Fame for television and has made several movie appearances as himself. In 2009, he received a "worst supporting actor" nomination for a Razzie award for his performance in Miss March.
A documentary by Brigitte Berman, Hugh Hefner: Playboy, Activist and Rebel, was released on July 30, 2010. He had previously granted full access to documentary filmmaker and television producer Kevin Burns for the A&E Biography special Hugh Hefner: American Playboy in 1996.
Hefner and Burns later collaborated on numerous other television projects, most notably on The Girls Next Door, a reality series that ran for six seasons (20052009) and 90 episodes.
In 1999, Hefner financed the Clara Bow documentary, Discovering the It Girl. "Nobody has what Clara had. She defined an era and made her mark on the nation," he stated