With a few photos of Marilyn Monroe, Hugh Hefner ignited a sexual revolution Photo by Charley Gallay/Getty Images for Playbo
LOS ANGELES, CA - JANUARY 16: Hugh Hefner poses at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)

America’s first playboy, Hugh Hefner, passed away on Sept. 27 of natural causes in his home surrounded by family.

His son Cooper Hefner confirmed the icon’s death in a statement.

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” he said. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history.”

Born in Chicago in 1926, Hefner served for two years in the U.S. Army at the end of World War II. In that time, he wrote for a military newspaper and was discharged in 1946.

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Hefner got his start in publishing as a copywriter for Esquire but left the position in January 1952 after he was denied a $5 raise. The following year, Hefner raised $8,000 from investors, including his mother, to launch Playboy. For the first issue of the magazine, which was originally going to be named Stag Party, Hefner purchased color photos from Marilyn Monroe’s 1949 nude “Red Velvet” calendar shoot with photographer Tom Kelley and put them in the centerfold. The issue quickly sold more than 50,000 copies and was an instant sensation. The magazine was founded soon after a time of war and economic depression, with the Korean war ending in 1953, the same year Playboy launched. For many, the publication brought a welcome change to a sexually repressed era.

Hefner went on to create Playboy Enterprises, Inc., which manages the Playboy empire. His brand once included 23 Playboy clubs, hotels and casinos. His businesses played an important role in the sexual revolution in America, and Playboy remains one of the most well-known brands in the world. Hefner chose iconic image of a bunny wearing a bow tie to distinguish the magazine from other men’s publications, as it was “frisky and playful” and it remains one of the most well-known symbols to this day.

Before he became the symbol for the single lifestyle, Hefner was married to Mildred Williams in 1949. They had two children together, daughter Christie Hefner and son David Hefner. Following his divorce, Hefner was reportedly involved with several Playboy Playmates before settling down with 1989 Playmate of the Year Kimberley Conrad. He and Conrad had two sons, Marston Hefner and Cooper Hefner. They separated in 1998, and Conrad moved into a home next to the Playboy Mansion. In 2012, Hefner married Playmate Crystal Harris. He was 86, and she was 26.

Hefner appeared on several television series including “Playboy’s Penthouse” (1959-1960) and “Playboy After Dark” (1969-1970) before going on to appear in one of the first reality TV series, “Girls Next Door,” with his three girlfriends at the time, Holly Madison, Kendra Wilkinson and Bridget Marquardt.

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Hefner was also a philanthropist during his lifetime. He donated and raised money for the Democratic Party and donated $100,000 to the University of Southern California’s School of Cinematic Arts. In 2010, he donated the last $900,000 to a fund to stop developers from purchasing the land around the iconic Hollywood Sign in California.

Hefner is survived by his wife Crystal and four children, Christie, David, Marston and Cooper. His estimated $43 million fortune has been promised to his children and a variety of charities, with an undisclosed amount going to the University of Southern California film school.

Hefner will reportedly be buried next to Marilyn Monroe at Westwood Village Memorial Park in Los Angeles.

Nicole is a content editor with Rare. 
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