Hugh Marston Hefner (April 9, 1926 – September 27, 2017) was an American businessman, magazine publisher, and playboy. He was the founder of Playboy and editor-in-chief of the magazine….which he founded in 1953. He was also the chief creative officer of Playboy Enterprises….which is the publishing group that operates the magazine. An advocate of sexual liberation and freedom of expression, Hefner was a political activist and philanthropist in several other causes and public issues.
Known to friends and family as simply “Hef,” in 1949, Hefner married Northwestern University student Mildred Williams….and they had two children….daughter Christie and son David. Before the wedding, Mildred confessed that she had an affair while he was away in the army…..as he called the admission “the most devastating moment of my life.” A 2006 E! True Hollywood Story profile of Hefner revealed that Mildred allowed him to have sex with other women….out of guilt for her own infidelity….and in the hope that it would preserve their marriage….when the two were divorced in 1959. Hefner remade himself as a bon vivant and man about town….a lifestyle he promoted 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 including Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Barbi Benton, Karen Christy, Sondra Theodore and Carrie Leigh were a few of his many lovers. 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.
In 1985, Hefner had a minor stroke at age 59….so, after re-evaluating his lifestyle, he made several changes….as the wild, all-night parties were toned down significantly….and in 1988, daughter Christie took over the operation of the Playboy empire. The following year, Hef married Playmate of the Year Kimberley Conrad…whereas they were 36 years apart in age….and the couple had two sons…. Marston Glenn born 1990 and Cooper Hefner born in 1991. The E! True Hollywood Story profile noted that the notorious Playboy Mansion had been transformed into a family-friendly homestead. After he and Conrad separated in 1998….she moved into a house next door to the mansion.
Hefner became known for moving an ever-changing coterie of young women into the Playboy Mansion, including twins Sandy and Mandy Bentley…..while he dated as many as seven women concurrently. He also dated Brande Roderick, Izabella St. James, Tina Marie Jordan, Holly Madison, Bridget Marquardt, and Kendra Wilkinson….as Madison, Wilkinson, and Marquardt appeared on The Girls Next Door depicting their lives at the Playboy Mansion. In October 2008, all three girls decided to leave the mansion….when after an 11-year separation, Hefner filed for divorce from Conrad citing irreconcilable differences. Hefner has stated that he only remained nominally married to her for the sake of his children and his youngest child had just turned 18. In January 2009, Hefner began a relationship with Crystal Harris….as she joined the Shannon Twins after his previous “number one girlfriend”, Holly Madison, had ended their seven-year relationship….On December 24, 2010, he became engaged to Harris, to become his third wife….but Harris broke off their engagement on June 14, 2011….which was five days before their planned wedding….when In anticipation of the wedding, the July issue of Playboy, which reached store shelves and customer’s homes within days of the wedding date….featured Harris on the cover and in a photo spread as well. The headline on the cover read “Introducing America’s Princess, Mrs. Crystal Hefner”. Hefner and Harris subsequently reconciled and married on December 31, 2011.
