Hugh Hefner, Playboy founder who built his empire in Chicago, dies at age 91

 In Entertainment
Some years ago, sitting in his castlelike mansion in the Holmby Hills neighborhood of Los Angeles, Hugh Hefner was telling a visitor about the Halloween party taking place there in a few days. It would be — what? — the 7,435th party of Hefner’s exceptional charmed and successful life, a lavish bash for 1,000 or so of his closet and most comely friends.

“Now, this is a costume party,” said Hefner. “You will have to wear a costume.” 

“I was thinking,” said the visitor, “that, with all due respect, I might get some pajamas, a robe, a pipe, slippers and a Pepsi and going as, well, the young Hugh Hefner.”

The then 73-year-old Hefner laughed. He gave a sly smile and said, “I’m sorry. That won’t work. I’m going as the young Hugh Hefner.”

Influential and controversial, admired and vilified, and seemingly forever young, the Chicago-born publisher of Playboy magazine and the Bunny-emblazoned empire that it spawned, Hugh Marston Hefner died peacefully at home Wednesday from natural causes. He was 91.

That life started on April 9, 1926, at Michael Reese Hospital, where he was born the first of the two children—younger brother Keith was born in 1929; he died in 2016 at 87 — of Grace and Glenn Hefner, she a schoolteacher and he an accountant and both originally from Nebraska.

The family lived in Chicago at 1922 N. New England Ave. in the Galewood neighborhood on the Northwest Side, where they attended Methodist church and the children went to Sayre Elementary School. When he was 8 years old, Hugh Hefner started a school newspaper called The Pepper, despite a warning from a concerned teacher that “if he continues to waste time on this, he will never amount to anything.”

“But I was a smart little boy,” he told a Tribune reporter in 1999.

He attended Steinmetz High School and later recalled, “The best time of my life before Playboy was my last two years at Steinmetz. It was a coming-of-age time. It was the first time I went steady. I was a class leader, writing and performing in plays and shows, working on the paper. The things I enjoyed were the things between classes.” 

One of his passions was cartooning, and as a teenager he created a magazine called Shudder and had a Shudder Club for all of his pals. He also started a cartoon autobiography called “School Daze,” which he continued while serving two years in the U.S. Army infantry and later in college. 

His other early passion was the movies. 

“There is no way to underestimate the effect movies had on me as a boy,” Hefner said. “My dreams came alive at the Montclare Theatre on Grand Avenue.” He remembered, as a child of the Depression, watching cinematic depictions of the roaring ’20s, “all those images of the Jazz Age, the flappers … and thinking that I’d missed the party.”

He would not miss many parties the rest of the way.

In 1946, after a brief stint at the Art Institute of Chicago, where he took a summer art course in anatomy, Hefner enrolled at the University of Illinois at Urbana-Champaign. By doubling up on classes, he graduated 21/2 years later with a bachelor of science degree, majoring in psychology. While at university, he edited the campus humor magazine, Shaft, introducing a feature he called “Coed of the Month.” He also drew cartoons for the campus newspaper, The Daily Illini. At the time, he began to develop a philosophy that linked freedom of speech and the press with individual rights and a rejection of what he called “our legacy of puritan repression.” 

“For me, journalism isn’t just one more profession,” Hefner said years later, when donating $500,000 to endow student fellowships in the university’s school of journalism. “It is one that goes to the heart of democracy.”

His own professional path began in Chicago with a job as a promotion copywriter for Esquire magazine. When that publication decided to move to New York, Hefner asked for a $5 raise to his $60-a-week salary. When it was denied, Hefner decided to stay behind and start his own magazine.

He was married by then and a father. He had wed his high school sweetheart, Mildred Williams, in 1949, and they shared their small apartment in Hyde Park with baby daughter Christie, born in 1952.

“The marriage was not good from the outset,” Hefner would later say. “We both had serious doubts before getting married. But I had no other game plan except to get married and, somehow, live happily ever after. But very soon I started becoming afraid that I was turning into my parents. I started to see that happening to my peers. People who were so much fun in high school were going dull. 

“I would walk around looking at the lights of high-rises. I felt like an outsider. I would fantasize about the lives that were going on inside those apartments and wonder whether I would ever be a part of it.” 

He mortgaged his furniture and took out a loan for $600 and borrowed $3,000 from friends and relatives to start Playboy. His initial idea was to start Chicago city magazine, an aim he redirected in 1953 when he found he could rent a naked picture of Marilyn Monroe from the Baumgarth Calendar Co. for $200.

And so Hefner put together the first issue of Playboy on his kitchen table. The first issue had no date because Hefner wasn’t sure there would be a second. 

That first issue came out in December 1953. It was 48 pages with a center spread featuring a nude calendar photo of Monroe. About 70,000 copies were printed. Nearly all sold within two weeks. 

The magazine was to be, Hefner said, “devoted to subjects I was interested in — the contemporary equivalents of wine, women and song, though not necessarily in that order.”

Hefner had originally wanted to call his magazine Stag Party, with a stag as its image, but that ran into copyright problems. So Playboy was chosen, and as the magazine’s first art director and first employee, local artist Art Paul, recalled, “We’d been talking about animals and we thought of the rabbit, the playboy of the animal world.” 

It took Paul only about an hour to sketch the famous rabbit head. He intended that it be “a quarter inch high, sort of a friendly signoff to articles.” The second issue of the magazine had the rabbit logo on the cover, as did every issue since in all manner of sizes and variations. It soon became such a recognizable symbol that a letter addressed only with that bunny once made it successfully from California to the company’s Chicago headquarters. It is as famous and recognizable as any logo of the 20th century, something that sits in the collective consciousness of the planet alongside McDonald’s Golden Arches, Disney’s Mickey Mouse, Apple’s apple or Nike’s swoosh. 

Quickly, the fledgling magazine moved into its first offices, at 11 E. Superior St., across the street from Holy Name Cathedral. A company that made kneeling pads was out back. To celebrate the first anniversary of Playboy in 1954, Hefner took his whole staff out to lunch. There were seven of them and they filled one booth at the old Charmet’s Restaurant, at Chicago and Michigan avenues. 

“I really wanted to focus on the good-life concept. A lifestyle. A point of view we were trying to express,” Hefner once said. “And we hit a nerve.’’ 

The magazine offered a new set of ethical values for an urban society. The message was loud and clear: Enjoy yourself. 

The magazine quickly reached a circulation of 1 million and then 2, 3 … topping out eventually at more than 8 million in the early 1960s and spawning magazine racks full of imitators, none nearly as successful. 

Hefner and his wife divorced in 1959. She got custody of the two children — Christie and her younger brother, David, who was born in 1955 — remarried and moved to the North Shore. 

Hefner moved into a 48-room mansion at 1340 N. State Parkway, affixed a sign near the door (translated from the original Latin it said, “If you don’t swing, don’t ring”) and began to cultivate an image and a lifestyle that would define him, his magazine and an era. 

“Obviously he wasn’t a hands-on father,” said Christie Hefner, who would as an adult serve as the chairman and chief executive officer of Playboy Enterprises. “But he was a good father. I had my 16th birthday party at the mansion. There was never a period of time when I didn’t see him.” 

In the heyday of the Playboy empire, in the 1960s and 1970s, Hefner’s life was an open magazine piece. Almost every month, somewhere in the world, a major publication did an analysis of Hefner and the Playboy phenomenon. When Tom Wolfe was inventing New Journalism, he made the Playboy Mansion a major stop on his epochal cross-country tour for the Sunday magazine of the New York Herald-Tribune. Time magazine accorded its highest laurel, a cover profile, to Hefner in 1967: “Hugh Hefner is the prophet of pop hedonism.”

In that story Time called Hefner “the first publisher to see that the sky would not fall and mothers would not march if he published bare bosoms; he realized that the old taboos were going. … He took the old-fashioned, shame-thumbed girlie magazines, stripped off the plain wrapper, added gloss, class and culture. It proved to be a sure-fire formula.” 

Millions of words have been written in an attempt to unravel that “formula.” 

Among the most intriguing come from Barbara Ehrenreich in her book “The Hearts of Men: American Dreams and the Flight From Commitment.” “(The real message of Playboy) was not eroticism, but escape — literal escape from the bondage of breadwinning.” 

The images of naked women, she wrote, “were necessary not just to sell the magazine, but to protect it. When, in the first issue, Hefner talked about staying in his apartment listening to music and discussing Picasso, there was the Marilyn Monroe centerfold to let you know that there was nothing queer about these urbane and indoor pleasures. And when the articles railed against the responsibilities of marriage, there were the nude torsos to reassure you that the alternative was still within the bounds of heterosexuality. Sex — or Hefner’s Pepsi-clean version of it — was there … to prove that a playboy didn’t have to be a husband to be a man.” 

Much of the press coverage of the time was devoted to the Playboy Mansion, where Hef holed up for much of the 1960s. Often, visitors found the living room awash in cables of some eager-beaver foreign film crews, chattering about Hefner’s cutting-edge electronics room or the Woo Grotto behind the downstairs swimming pool.

What was off-limits to casual visitors was the tucked-away Roman Bath, reached by a narrow stairwell descending from Hefner’s bedroom, which featured a round, rotating bed from which, for years, he conducted his share of the business of the magazine/entertainment empire.

The Roman Bath, say several who saw it, included baroque gold spigots and faucets that sprayed and showered, a tub with chest-high water and, in a separate alcove, a mink-covered waterbed lying under a mirrored ceiling.

Among impressed visitors was Italian journalist Oriana Fallachi. In a much-quoted essay, she told of what she had found on a trip to Chicago: “First of all, the House. He stays in it as a pharaoh in his grave, and so he doesn’t notice that the night has ended, the day has begun, a winter passed, and a spring, and a summer — it’s autumn now. Last time he emerged from the grave was last winter, they say, but he did not like what he saw and returned with great relief three days later. The sky was again extinguished beyond the electronic gate, and he sat down again in his grave: 1340 North State Parkway. But, what a grave, boys!’’

In the mid-1960s, friends worried about the Near North Side recluse, with irregular sleep habits, whose weight had dropped to 135 pounds, despite a diet built around fried chicken and candy bars. In 1968, he decided to mend his ways, “part of a new image called living longer,’’ he said. He started to eat wholesome foods, slept more, put on 40 pounds, rethought his wardrobe, bought a DC-9 jet and had it fitted with a James Bond interior and a Bunny logo on its upswept tail.

By 1971, when Playboy Enterprises went public, the magazine was selling 7 million copies a month, there were 23 Playboy clubs, resorts, hotels and casinos, along with ventures in book publishing, merchandising, modeling, records, TV, movies and a limousine company. The corporation employed 5,000 people, including 1,000 waitresses, dressed in skimpy black silk costumes and known as Bunnies.

That same year, attracted by the entertainment possibilities of the West Coast, he set up a second residence in Los Angeles, buying a 51/2-acre estate in Holmby Hills. By 1975, the Chicago mansion was donated to the School of the Art Institute as a student dormitory and later converted into private condominiums. But the company’s headquarters remained in Chicago, in two locations, in the former Palmolive Building and a later space on Lake Shore Drive.

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