Hugh Hefner, founder of the Playboy empire and unofficial leader of the 60’s sexual revolution, has died at his home in LA surrounded by his family. He was 91.

The businessman, media mogul and world-reknowned playboy made his own big break in 1953. After working a series of small, unsatisfying jobs at various magazines, he founded Playboy with $8,000, $2,000 of which came from his brother and mother. The first issue featured a nude photo of Marilyn Monroe which readers went crazy for, buying 53,000 copies. According to Variety, the brand quickly became known for its combination of sophistication and sex appeal, pairing professionally taken nude photos with more serious interviews and columns from well-known writers and figures. Hefner went on to create Playboy nightclubs, a talk show, various TV series and more.

The magazine came into the public eye during the revolutionary 1960s through the 1970s, when free love, drugs, and general hedonism were all the rage. The Playboy mansion, Hefner’s home for decades, became a hotspot in the Hollywood social scene and helped turn Hefner into a cultural icon. He was known as the ultimate playboy, dating and sometimes marrying young twenty-something Playboy Bunnies well into his eighties. He’s known for launching the careers of many of his models, dubbed “Playboy Bunnies,” and boosting a long line of famous actors and actresses who posed for the magazine. He even tried his hand at filmmaking, co-producing Roman Polanski’s “Macbeth” and Monty Python’s first film “And Now for Something Completely Different,” according to THR.

Hefner frequently drew the ire of feminists, some of whom felt he objectified women, while others felt he honored them. While it’s not clear that Hefner believed in feminism himself, he was a public supporter of a women’s right to choose and same-sex marriage, helping to fund the Rowe v. Wade landmark decision in 1973.

Hefner is survived by his wife Crystal and children Christie, David, Marston Glenn and Cooper Bradford. Cooper paid tribute his father Wednesday night, saying:

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 defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises

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