Hugh Hefner, Between the Headlines

The end of an article in 1957 noted that the magazine had a record circulation in the first quarter of the year, estimated at 880,590.

Censors caught on soon enough. The next year, an effort by the post office to keep the magazine out of the “mails” failed.

And Mr. Hefner himself was quoted in a 1960 Associated Press piece about a ban on the magazine at newsstands in Connecticut, saying that Playboy would be distributed in the state, “if I have to go there and sell it myself.”

Celebrity on the Rise

A tiny item, fewer than 50 words long, in January 1962, heralded Mr. Hefner’s growing profile at the dawn of the sexual revolution. His life story was to be featured in a movie. Its title? “Playboy.”

His empire’s momentum was becoming difficult to stop, though many tried. New York’s state liquor authority delayed a license for The Playboy Club in December 1962. But by April 1963, the club was the “busiest in the city,” The Times reported, with 2,700 people visiting daily to “eat, drink, listen to music and gaze at scores of lightly clad young women wearing rabbit ears on their heads.”

A year later, Mr. Hefner, then the subject of his first feature-length Times profile, had not yet mastered his public persona. Though Mr. Hefner seemed to be trying to “convey the impression that he is living a ‘bachelor’s dream,’” the reporter saw the impresario as a “gaunt and rather somber young man” — a remote person whom friends described as a “loner.”


Mr. Hefner in 1969 with a group of women at his London club.

Central Press, via Getty Images

At the Center of Everything

By 1968, the world had shifted, and Mr. Hefner’s libertine values were shared by much of a generation.

Charlotte Curtis, who later became the first woman on The Times’s masthead, captured the scene at a weeklong party at Mr. Hefner’s mansion in Chicago, during the Democratic National Convention:

The allegedly beautiful people of the Democratic National Convention were playing with Hugh M. Hefner’s waterfall button early this morning, sending his waiters to the kitchen for everything from steaks to scotch, tilting his pinball machine and clustering around the color television set that disappears behind a painting.

Ms. Curtis’s remarkable story — featuring cameos from a withdrawn Warren Beatty, Adlai E. Stevenson’s son, and the mayors of Boston and Cleveland — described the events of Aug. 28, which was also the day of the Chicago Police riot that became one of the defining moments of the decade. (Norman Mailer is absent, “out with the hippies.”)

The ‘Hare Apparent’

The chaos of the era did not spare Playboy. By 1970, a television review in The Times panned Mr. Hefner as an “aging anti-feminist” whose “notions of presenting sexy ecology are worn and unimaginative.” The same year, he was called a “fascist” and a “pig” as members of the women’s liberation movement protested his appearance on the Dick Cavett show.

A series of questionable business moves by Mr. Hefner, including financing movies and taking his company public, cut into his profits, as did increasing competition from publishers willing to be more explicit than Playboy.

And in 1975, Mr. Hefner’s social secretary, who had been charged the year before with intent to distribute cocaine, died of a prescription drug overdose. For many, the party was over; the Chicago Playboy mansion closed that year. (It would later be turned over to the Art Institute of Chicago, which made it into a dorm.)

By the late 1970s, the magazine was plagued by financial problems, its reputation damaged as the feminist movement grew.

Enter 26-year-old Christie Hefner, Mr. Hefner’s daughter from his first marriage.

Critics called the young, conservatively-dressed Ms. Hefner a figurehead who had been elevated to deflect criticism of the magazine. Her father did not entirely disagree.

“Well, I have made the comment that if Christie hadn’t existed, our promotion department might want to invent her,” he confessed in a 1979 interview. “She’s rather ideally suited, both symbolically and actually, for the role that she’s playing in the company.


Mr. Hefner on the Playboy jet in 1970.

Central Press, via Agence France-Presse — Getty Images

‘Father Rabbit’

But Ms. Hefner proved to be no figurehead. In 1982, she became president of Playboy, and two years later, the chief of operations.

Still the decline continued. In 1985, Mr. Hefner had a mild stroke, one that he credited with giving him a new outlook on life.

That became clear to the public three years later, when Mr. Hefner, 62, announced his plan to marry Kimberley Conrad, a 24-year-old model. That same year, he relinquished the chairmanship of Playboy to his daughter.

Where Mr. Hefner had been revolutionary in his marketing of the playboy lifestyle, his thoughts on the subject of marriage were less groundbreaking. (He had been married once before and would marry once again.)

He called his coming nuptials “the logical culmination of my life” and said his relationship with Ms. Conrad was “the best I’ve ever had.” He reported that the two shared a love of animals and “simply hanging out” at home.

Mr. Hefner did not disappear, of course. He appeared on a reality show starring his much younger girlfriends and was featured in The Times as recently as 2011, with an article titled “How Hef Got His Groove Back.” But a 1992 profile (headline: “Father Rabbit”) revealed that Mr. Hefner was content in hibernation. The controversy of the brand he had created had become old news.

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