Hugh Hefner, who died this week at 91, never quite made it to maturity. That was the source of his regal riches. It was also the reason for his imperial downfall.

The child of puritanical parents, Hefner grew up in Chicago, graduated from the University of Illinois, served in the army, and married young, but he never felt at home in the Eisenhower era. After a stint as a copywriter for Esquire, he borrowed $8,000 and founded Playboy. Featuring a centerfold of Marilyn Monroe before she became Marilyn Monroe, the magazine was an overnight sensation. The first issue sold 50,000 copies; by the conclusion of its second year, the magazine had 7 million subscribers. Subsequent issues became famous (and notorious) for their full-color portraits of unclothed, airbrushed women, as well as for their monthly celebration of sex without responsibility, part of a sybaritic lifestyle of bachelor pads, waterbeds, and wet bars.

That was only the beginning. As the magazine took off, Hefner expanded his empire. Playboy clubs sprung up in major cities, inviting lonely bachelors to gawk at Playboy Bunnies—attractive young women in abbreviated rabbit uniforms, complete with long ears and fluffy cottontails. Feminist writer Gloria Steinem went undercover to serve as a Bunny. “I learned what it’s like,” she recalled, “to be hung on a meat hook.”      

Predictably, Hefner’s first marriage ended in divorce, whereupon he went public with his dalliances in the Playboy Mansion—complete with a dimly lit grotto, a waterfall, and a swimming pool—in the Holmby Hills section of Los Angeles. Puffing his ever-present pipe, caparisoned in a silk bathrobe, and surrounded by comely blondes, brunettes, and redheads, “Hef” proclaimed himself an original feminist and something of a public intellectual. As credentials, he touted his backing of Roe v. Wade and Playboy’s distinguished roster of contributors, including John Updike, Isaac Bashevis Singer, and Vladimir Nabokov; and its interviewees, including Martin Luther King, Jr. and Jimmy Carter.

But to born-and-bred New Yorkers, the Playboy brand never really caught on. When we saw a bunny decal on a side window, we knew that the driver probably had a pair of soft dice dangling from his rearview mirror, along with fins in the rear and a lot of road rage. Eventually, the whole enterprise began to show a squalid weariness that we had detected early on. Hef’s second marriage crashed and burned, Larry Flynt’s Hustler grabbed a major share of the soft-porn market, and Playboy’s circulation dwindled to 800,000. Soon the clubs closed down and the mansion began showing its age.

In 2006, Izabella St. James, one of Hef’s former girlfriends, published Bunny Tales. “Everything in the Mansion felt old and stale,” she wrote, “and Archie the house dog would regularly relieve himself on the hallway curtains, adding a powerful whiff of urine to the general scent of decay.”

Hef married for the third time in 2012, but this time, there were few photographs of the groom, the bride (60 years his junior), or his four children, some now carrying AARP cards themselves. Hef suffered from a series of health problems and sported hearing aids. The Hefner fortune, once estimated at $200 million, had lost more than three-quarters of its former worth. Five years later, it remains moribund.

In the end, perhaps the kindest way to remember Hugh Hefner is not as a superannuated swinger, but as an American journalism innovator at a time when millions actually subscribed to monthly magazines printed on glossy paper. In that regard, Hef belongs in the company of Henry Luce (Time), DeWitt Wallace (Reader’s Digest), Gardner Cowells (Look), and others who made a difference, once upon a time—a time, that is, before new social mores, the Internet, and the 24-hour news cycle rendered them and their publications as obsolete as the printing press.

Photo by Dan Kitwood/Getty Images


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