Hugh Hefner

In January 1952, Hugh Hefner left his job as a copywriter for Esquire after he was denied a $5 raise. In 1953, he took out a mortgage, generating a bank loan of $600, 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 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 in 1992 for $75,000.) After the Charles Beaumont science fiction short story “The Crooked Man” was rejected by Esquire magazine in 1955, Hefner agreed to publish the story in Playboy. The story highlighted straight men being persecuted in a world where homosexuality was the norm. After the magazine received angry letters, 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.” In 1961, Hefner watched Dick Gregory perform at the Herman Roberts Show Bar in Chicago. Based on that performance, Hefner hired Gregory to work at the Chicago Playboy Club; Gregory attributed the subsequent launch of his career to that night. On June 4, 1963, Hugh Hefner was arrested for promoting obscene literature after an issue of Playboy that featured nude shots of Jayne Mansfield was published. The case went to trial and resulted in a hung jury. During the civil rights era in 1966, Hefner sent African-American Alex Haley to interview George Lincoln Rockwell, much to Rockwell’s surprise because Haley was black. Rockwell had founded the American Nazi Party and would be later described by some as the “American Hitler”. Rockwell agreed to meet with Haley only after gaining assurance from the Playboy writer that he was not Jewish, although Rockwell kept a handgun on the table throughout the interview. The interview was recreated in Roots: The Next Generations, with James Earl Jones as Haley and Marlon Brando as Rockwell. Haley had also interviewed Malcolm X in 1963 and Martin Luther King Jr. in 1966 for the newly established 1962 “playboy interview”.

In the 1993 The Simpsons episode “Krusty Gets Kancelled”, Hugh Hefner guest-voiced himself. 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. Hugh Hefner guest-starred as himself in a 2006 episode of Seth Green’s Robot Chicken on the late-night programming block Adult Swim. He has a star on the Hollywood Walk of Fame for television and made several movie appearances as himself on the small screen. In 2009, he received a “worst supporting actor” nomination for a Razzie award for his performance as himself in Miss March. On his official Twitter account he joked about this nomination: “Maybe I didn’t understand the character.” 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 Biographyspecial 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 (2005–2009) and 90 episodes. In 2012, Hugh Hefner announced that his youngest son, Cooper, would likely succeed him as the public face of Playboy.

In 1949, Hugh Hefner married Northwestern University student Mildred (“Millie”) Williams. They had two children: daughter Christie (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.” 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. The two were divorced in 1959. Hugh 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. Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Barbi Benton, Karen Christy, Sondra Theodore, and Carrie Leigh – who filed a $35 million palimony suit against him – were a few of his many lovers. In 1971, he acknowledged that he experimented in bisexuality. Also 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. After re-evaluating his lifestyle, he made several changes. 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, he married Playmate of the Year Kimberley Conrad; they were 36 years apart in age. The couple had two sons: Marston Glenn (born 1990) and Cooper Bradford (born 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.

Hugh Hefner became known for moving an ever-changing coterie of young women into the Playboy Mansion, including twins Sandy and Mandy Bentley. 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. 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. After an 11-year separation, Hefner filed for divorce from Conrad, citing irreconcilable differences. Hugh 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; 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. Harris broke off their engagement on June 14, 2011, five days before their planned wedding. 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”. Hugh Hefner and Harris subsequently reconciled and married on December 31, 2012. Hefner’s brother Keith died at the age of 87 on April 8, 2016, one day before Hefner’s 90th birthday. Hugh Hefner died at his home in Holmby Hills, Los Angeles, California, on September 27, 2017, at the age of 91. His ashes were interred at Westwood Memorial Park in Los Angeles, in the crypt beside Marilyn Monroe. “Spending eternity next to Marilyn is an opportunity too sweet to pass up,” Hefner had told the Los Angeles Times in 2009.