Hugh Hefner, the enigmatic figure behind Playboy magazine and the de facto empire it launched, was found dead in his home, the Los Angeles manse nicknamed the Playboy Mansion, on Wednesday. He was 91.
Considered the quintessential and iconic ladies’ man of the mid-20th century, the dawn of Hefner’s Playboy enterprise began in 1953 with the first issue of Playboy, a publication which the then-27-year-old married father of one envisioned as a guidebook for the cosmopolitan male.
“We enjoy mixing up cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex,” Hefner wrote in his first editorial for the magazine, capturing the persona he would eventually come to represent.
Playboy would come to have a circulation in the millions, leaving a legacy associated with nude centerfolds and groundbreaking journalism.
But Playboy would feasibly be a footnote without the presence of the man behind it. An entrepreneurial spirit who expanded his brand into a string of clubs, merchandise and into the seams of American pop culture itself, it’s impossible to pinpoint where Hefner’s reputation as a Casanova and sophisticate ended and where the self-same infusion of this projection began.
Hugh Hefner, Cannabis Crusader
Hefner was also a well-known cannabis advocate, who was quick to preach the virtues of pot and to donate his money and time to groups like the National Organization for the Reform of Marijuana Laws (NORML).
As NORML founder Keith Stroup recalled in 2011, it was a lawyer employed by Green Party politician Ralph Nader who suggested he reach out to Hefner to secure funding for the activist group in the early 1970s.
“One of [Nader’s] young lawyers named John Esposito said to me, ‘Keith, have you checked with the Playboy Foundation?’” Stroup said in an interview at the time.
“We were in the process at that point of sending funding proposals out to any foundation we could identify where we thought it might be possible that they would give us some funding,” Stroup continued. “And frankly, on the first eight or 10 we sent out, I didn’t get anything back but standard rejection letters. I hadn’t even been allowed to come and interview personally. So clearly, it was still considered by most foundations too hot to handle.”
Stroup followed the lawyer’s advice, soliciting the Playboy Foundation for a grant. Subsequently, his request lead to a meeting with Hefner in Chicago, who then offered Stroup $5,000 in grant money—and thus securing NORML’s significant part in the legalization movement.
Fittingly, the very existence of High Times would be in question without the existence of Playboy, Hefner’s flagship enterprise. Founded in 1974, High Times was modeled as a cannabis-infused spoof of Hefner’s magazine, as founder Thomas King Forçade made apparent from its very first issue.
Initially approached as a parodical one-off, High Times’ inaugural cover was an overt hat-tip to the Playboy centerfolds of yesteryear, featuring a young woman holding a psychedelic mushroom to her lips in an erotic, artful pose. The first print run, which numbered around 10,000 copies, quickly sold out, leading to two reprints and a solid place in American counterculture.
Final Hit: Remembering Hugh Hefner
Along with his advocacy regarding the pro-cannabis movement, “the Pajama Man,” nicknamed for his proclivity for wearing custom silk PJs at all hours, is remembered for stoking controversy when it came to other causes.
Known for his progressivism when it came to civil and LGBT rights, Hefner and his magazine played a major part in spurring the end of 1950s puritanism and vitalizing the sexual revolution. While Playboy featured articles that decried racism and the persecution of queer people, he was disparaged by feminists, the latter of which claimed his empire contributed to the ongoing objectification of women.
Feminist icon Gloria Steinem went as far as to go undercover as a Playboy bunny at one of Hefner’s many “gentlemen only” clubs in 1963, resulting in a two-page exposé on his chain’s misogynist working conditions for the now-defunct Show magazine.
“I think Hefner himself wants to go down in history as a person of sophistication and glamour,” Steinem later recounted. “But the last person I would want to go down in history as is Hugh Hefner.”
Despite this dark mark on his complicated and fraught legacy, Hefner is also remembered for championing for sexual autonomy during an era of conformity. A supporter of contraceptives and pro-choice in an age before Roe v. Wade, a protector of the counterculture during the last throes of McCarthyism, Hef was and will always be known for bucking the system—and looking cool while doing it.