Born in Chicago in 1926, Hugh Hefner was born into a family that he described as being “conservative, Midwestern, [and] Methodist”. After finishing high school in Chicago, Hefner began his writing career in while serving in the Military in World War II. He would go on to write for Esquire magazine but would eventually quit after they refused to give him a 5 dollar raise.
Hefner founded Playboy in 1953 with $600 of his own money and built the magazine into a multimillion-dollar entertainment empire that at its 1970s peak included TV shows, a jazz festival and a string of Playboy Clubs whose cocktail waitresses wore bunny ears and cottontails. The magazine tycoon helped challenge the Western worlds ideas of sexuality in the public eye.
In 1949, Hefner married Northwestern University student Mildred Williams. They had two children: daughter Christie Hefner (born 1952) and son David (born 1955). Before the wedding, Mildred confessed that she had an affair while he was away in the army. He called the admission “the most devastating moment of my life.” This event seemed to change Hefner in a very profound way. Hefner revealed that Mildred allowed him to have sex with other women, out of guilt for her infidelity and in the fond hope that it would preserve their marriage. The two were divorced in 1959. This event seemed to set the tone for his womanizing way for the rest of his life.
Hefner adopted a “man about town” persona and began to spend time with as many women as possible. He promoted this lifestyle in his magazine and two TV shows he hosted, Playboy’s Penthouse (1959–1960) and Playboy After Dark (1969–1970). He admitted to being “‘involved’ with maybe eleven out of twelve months’ worth of Playmates” during some of these years.
Here’s a clip of Playboy’s Penthouse from 1959:
In 1971, Hefner established a second residence in Los Angeles with the acquisition of Playboy Mansion West and, in 1975, moved there permanently from Chicago.
Although Hefner was known to have many girlfriends, up to 7 at any time. He was only married three times. From these marriages, Hefner has four children. His polyamourous relationships were depicted on the show The Girls Next Door which ran for six seasons and was quite popular.
Hefner was also involved in philanthropy throughout his career and he had an affinity for protecting free speech. The Hugh M. Hefner First Amendment Award was created by Christie Hefner “to honor individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans.”
An interview with Hefner for TIME