Hugh Hefner who founded Playboy magazine 60 years ago died of natural causes Wednesday at age 91 at the Playboy Mansion. Hefner started Playboy in 1953 to create a men’s magazine that featured nude women, prominent interviews, feature articles and fiction. Marilyn Monroe was on the first cover before she became famous. America had never seen such a magazine and Hefner received credit for being the leader of the Sexual Revolution. But his progressive approach to sexuality caused him to clash with authorities who were not always ready to embrace the future. In 1963, he was arrested for promoting obscene literature because the magazine had nude photos of Jayne Mansfield. The case resulted in a hung jury. There was an emphasis on the nude bodies in the pages but the magazine was just as known for publishing some of the most important writers of the 20th century including Hunter S. Thompson, Margaret Atwood and Gabriel Garcia Marquez among others. Alex Haley famously interviewed Miles Davis for the publication in the ’60s.

Playboy magazine was the catalyst for Hefner’s Playboy clubs where Dick Gregory got his first big break after Hefner saw him performing in a Chicago night club. In 1959 he started the Playboy Jazz Festival at the Chicago Stadium in his hometown that would host the biggest names in jazz over the decades. He was the host of Playboy’s Penthouse and Playboy After Dark for two seasons in the ’60s. The Playboy Mansion was a site where legendary parties took place with some of the biggest entertainers in attendance.  The University Of Southern California’s School Of Cinematic Arts and the Much Love Animal Rescue were two of many organizations to receive his philanthropic efforts through his Hugh M. Hefner Foundation. Playboy inspired Douglas Lambert to create Playgirl magazine in 1973 which featured photo spreads of nude men marketed to women. In the ’80s’ when Vanessa Williams was involved in the naked photo scandal that took away her Miss America crown Hefner refused to buy the pictures and publish them because he did not want to embarrass her and he understood that her nomination was a historical moment for Black people. He championed the legalization of gay marriage and he eventually became a political independent after previously supporting the democratic party. Hefner also appeared in a number of films during his lifetime and last appeared in 2008’s The House Bunny.

Watch The Brand New Heavies, Siedah Garrett and Q-Tip in the video for The Ummah remix of “Sometimes” that was filmed at the Playboy Mansion and features early footage of Hugh Hefner:

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Azealia Banks has revealed her cover for the April 2015 issue of Playboy and inside she gives another one of her controversial interviews. She addresses racism, reparations, her disdain for middle American and her ultimate plan to live outside the country. The issue goes on sale this week.