The image of Hugh Hefner wearing a red silk dressing gown while smoking a pipe and being surrounded by scantily clad blondes is arguably the quintessential depiction of a bachelor's life. It represents a carefree view of a life where there are no rules or responsibilities. The business tycoon and Chief Creative Officer of Playboy Enterprises has died of natural causes this Wednesday (27th September) in his beloved Playboy Mansion. He was 91 years old and is survived by his wife, Crystal Harris.

Early life

Born on April 9 1926, in Chicago, Illinois, Hugh Marston Hefner was the first child of Grace and Glenn Hefner and had a brother, Keith (1929-2016).

He started his writing career in 1944 when he wrote for a U.S Army magazine during WWII. After graduating from the University of Illinois at Urbana Champaign in 1949 with a bachelor's degree in psychology and a minor in creative writing, he became a copywriter for "Esquire". After quitting in 1953 due to a refusal for a $5 pay rise, "Playboy" (initially Stag Party) was born in his Hyde Park kitchen, costing $600 out of his own pocket.

Playboy's Legacy

"Playboy" was first launched in December 1953 with Marilyn Monroe acting as the magazine's first centrefold model. From then on, it has become one of the biggest magazine targeting men and media empires in the world. From the iconic bunny costumes present in films such as "Legally Blonde" and "Bridget Jones' Diary" to Anna Faris playing the titular "House Bunny" in the 2008 film about a Playmate looking after a group of sorority girls, Hefner's image has influenced the entertainment and magazine industry.

"Playboy" became a trailblazer for nudity in the mainstream at a time where it was considered taboo. Despite being infinitely well known more for its content than its prose, the magazine has been given a fair amount of pedigree over the years. "Playboy" many influential authors, including Margaret Atwood, Vladimir Nabokov and Joyce Carol Oates.

A number of celebrities, politicians, and activists have also been interviewed during the magazine's lifetime, including Martin Luther King Jr, Malcolm X, Jimmy Carter and John Lennon and Yoko Ono.

Although Playboy magazine sales had gradually dwindled over the decades, Hefner's further business exploits still made it relevant.

From jewellery worn by women in velour tracksuits to the reality shows starring his Playmates, the icon of a rabbit in a side profile and wearing a bow tie was seen everywhere. Hefner sold the Playboy Mansion in 2016 (the time when Playboy briefly stopped publishing full frontal nude photos) for $100 million to his neighbour Daren Metropoulos. Part of the agreement of ownership was that Hefner was allowed to stay in the mansion until his death.


Hefner had married three times in his life. He married first wife Mildred Williams from 1949 to 1959, with whom he had two children: daughter and former chairman and CEO of Playboy Enterprises, Christie Hefner (born 1952) and son David Hefner (born 1955).

After suffering a minor stroke in 1985, he toned down his sleazy persona and went on to marry 1989's Playmate of the Year Kimberly Conrad from 1989 to 2010, with whom he had sons Marston Glenn (born 1990) and successor to Playboy Enterprises Cooper Bradford (born 1991). Despite separating in 1998, Conrad had moved into a home next to the Playboy Mansion. Hefner went on to marry his third wife, Crystal Harris, in 2012, who was sixty years his junior.

During this time, Hefner was infamous for dating many girlfriends at one time. Exclusively from his group of Playmates, Hefner would have on average three women with himat social events. Starting with Barbi Benton in 1969, his endless list of girlfriends would include Holly Madison, Bridget Marquardt, Kendra Wilkinson and the Shannon twins.

Sleazebag or Sexual Revolutionary?

The public's consensus of Hefner and his lifestyle was polarizing, to say the least. The idea of having twenty-something buxom blondes living in a lavish mansion together sounds more like the fantasy of a hormonal teenager than a legitimate business venture.

A philanthropist throughout his life, Hefner believed Playboy was about sexual liberation and freedom of speech. Involved in numerous charity and civil rights endeavours in his life, his achievements were unprecedented of at the time. From funding court cases challenging birth control rights and opening rape crisis centres, to standing up for abortion rights, Hefner's influence is not only present in the world of journalism, but oddly enough, feminism.

Hefner will be buried in a Los Angeles cemetery in an area next to Marilyn Monroe which he acquired in 1992.