Hefner founded Playboy in 1953 and published the first issue of the magazine from his apartment’s kitchen table. The first cover featured a pinup of Marilyn Monroe and lacked a publication date in case it sold poorly. The magazine was an instant success, with the debut edition selling more than 50,000 copies. By the end of the 1950s, the publication sold more than a million copies a month.

The magazine grew famous for its journalism and for the models that graced its pages. Despite Playboy’s reliance on nudity, Hefner never thought of it as solely a sex magazine, he told CNN in 2002. It regularly featured heavy topics, with in-depth interviews with historical figures like Fidel Castro, John Lennon, and Malcom X. The magazine embodied both intellectual and visual appeal, and was a beacon of the 1960s sexual revolution. Time Magazine featured Hefner on its cover in 1967 and dubbed him a “prophet of pop hedonism.”

Over the years, Hefner’s legend grew as he married his magazine’s “playmates” and appeared in reality TV shows with his girlfriends. Hefner’s trademark look—a silk robe and a lit pipe—made his image one of luxury and indulgence.

Check out Hugh Hefner’s life in photos above.