An American entrepreneur, Hefner is a publisher, film producer, music publisher, book publisher and owner of a record company, theaters, model agency, gambling casinos, limo service and bunny paraphernalia. He started Playboy magazine in 1953 with $600 borrowed against his wedding furniture. In 1960 he started the first Playboy Club in Chicago, and by age 40 he was worth well over $100 million. In 1972 he started Oui, a magazine that runs a bit more raunchy layouts, to compete with Hustler. Hefner has two mansions, each with its own hostess, Karen Christie in Chicago (from 1971), and Barbi Benton in Playboy West, Los Angeles (from 1968). He was once quoted as saying that he’d made love to more than a thousand women.
“Hef” says that most of what he does is related to his childhood. He was raised in a typical Midwestern American Methodist Puritan home where there was no outward show of love or emotion, not so much as a kiss on the cheek. He did feel that he was loved, but there was simply no demonstration. His mom later invested $1,000 in Playboy, not because she believed in what the magazine meant but because she believed in her son, and his dad later came to work for him. His folks taught him tolerance, idealism, honest and lack of bigotry, but he wrote, “I don’t think that they ever fully appreciated the positive impact that Playboy and my life have made on society.” He married his first wife, Mildred, in June 1949 and had two kids with her; the marriage ended in divorce.
Hef reinvented himself in 1960 when he became Mr. Playboy and started living the life espoused by his magazine. He entered show business, bought the first Playboy mansion in Chicago and opened the first Playboy Club, all within six months. “I became the person I wanted to be. I started wearing the smoking jacket and using the pipe as a prop. I was driving around in a Mercedes-Benz.” Hef had a setback when he suffered a stroke on 7 February 1985 at 2:00 AM that put him to bed for a whole two weeks. However he let up on business, turning the company reigns over to Christie. He met his second wife, Kimberly Conrad, in May 1987 and they married on 1 July 1989, eventually having two sons. In 1998 he and Kimberly separated amicably when he moved her into a house next door. He resumed his social life, entertaining as usual at home wearing silk pajamas (custom-made at $250 a pair), but also hitting the party circuit with Mandy, Brande and Sandy. At 77, he touts the benefit of Viagra and has given a nod to cosmetic surgery with “a little tuck on his neck in late 1998.” He still has the winning recipe for a great party: Hollywood celebrities, his own chef and staff and his firm belief in a three-women-for-every-man ratio. He is quoted as saying, “My life is an open book. With illustrations.”
At the Christmas holidays in 2010, Hefner became engaged to marry 24-year-old Crystal Harris. The wedding was scheduled for 18 June 2011 but a few days before, Harris cancelled, saying she was having second thoughts.
In 2013 Hefner announced that his youngest son, Cooper would succeed him and eventually help run the Playboy Empire.
Hefner died at his home in Holmby Hills, Los Angeles, California on 27 September 2017, at the age of 91.
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