91-year-old Hugh Hefner, the head of the popular men’s magazine, “Playboy,” died at his home in Holmby Hills, in Los Angeles on Wednesday. He died of natural causes.

Hefner started his magazine empire in 1953, and his very first issue struck gold, when he included Marilyn Monroe’s 1949 photo shoot that he had bought for $200. The pictures originally were for a calendar that was supposed to be issued in 1949. That first edition of the popular men’s magazine sold over 50,000. 

He had his idea for the magazine, and acted on it after quitting his job as a copywriter for Esquire, in 1952. He had begun work at the Esquire after he got out of the army, where he was a writer. He quit that job over the magazine’s refusal to give him a $5 raise.

In 1960, Hefner’s empire grew considerably, following the opening of the first Playboy Club in downtown Chicago. The chain of clubs quickly went international with club openings in London and Jamaica. Customers could lounge in the living room, socialize in the playmate bar, hang out in the club room, or dine in the club’s dining room, and soon became the go-to spot for top entertainers, musicians and comedians.

By 1963, Hefner found himself in court, charged with obscenity, after publishing pictures of Jayne Mansfield. But, that trial ended in a hung jury.

Continuously surrounded by his Playboy Bunnies, and always with his trademark pipe, Hefner quickly became known as the man-about-town and was invited to movie premiers and the most popular night clubs. He would shuttle from city to city on his highly personalized DC-9 that he named the “Big Bunny.”

Known for his dating of beautiful women, Hefner, at times dated as many as seven simultaneously.[xyz-ihs snippet=”Adsense-responsive”]But, Hefner toned down his “clubbing'” in 1985, after suffering a minor stroke. It was after that that Hefner turned his empire over to his daughter Christie, got married to Kimberly Conrad, and the mansion slowed down from the raucous party house, to more of a homestead. Hefner would later move from the mansion, to a house next door. 

Besides his notoriety as a man-about-town, and lavish parties, Hefner was also a philanthropist and contributed to many causes throughout his life. Because of his support for conservation societies, Hefner would have a species of rabbit named after him, the Sylvilagus palustris hefneri.

Although Hefner never met Marilyn Monroe, he bought the  crypt next her at the Westwood Village Memorial Park Cemetery in 1992. He said of the purchase in 2000, that he felt a connection to Marilyn, as she was his first centerfold, which he felt launched his career, and that she was born the same year as he.

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