In 1977, at the age of 51, Hugh Hefner endured an existential crisis when he found himself choking on a metal Ben Wa ball, one of a pair that had been in his girlfriend Sondra Theodore’s vagina in order ‘to enhance her physical sensations’. The ruler of the then considerable Playboy empire ‘fell back on the bed, choking and unable to breathe, and was about to lose consciousness when she squeezed his chest and finally dislodged the sphere’. (I’m quoting from Steven Watts’s 2008 biography, Mr Playboy.) ‘Is this what it has all come to?’ Hefner later wondered aloud. Then: ‘What will all the newspaper headlines in the world say tomorrow morning?’ Finally, regaining his composure, he asked: ‘Are we getting this on videotape?’

Hefner’s death yesterday at the age of 91 made many if not all the world’s newspaper headlines. In a number of ways he was a conventional Midwesterner of his generation. His somewhat strict Methodist upbringing was in no way out of the ordinary. The family’s circumstances were modest but never strained. Hugh, the older of two boys, was a bright, if easily distracted, pupil. He worked for the high school paper, the Steinmetz Star, as a reporter, cartoonist and circulation manager. On graduating from high school his class voted him ‘Most Likely to Succeed’, ‘Most Popular Boy’, ‘Class Humorist’, ‘Best Orator’, ‘Best Dancer’ and ‘Most Artistic’. He was still a virgin though.

The first issue of Playboy appeared in November 1953, featuring photographs of Marilyn Monroe taken four years earlier with, as she joked, ‘nothing on but the radio’. Hefner bet everything he had on it, along with quite a bit of what his friends and his mother were willing to part with. It sold 54,000 copies of its print run of 70,000. In its best year, 1972, Playboy’s circulation was 7,161,561.

Hefner spent most of his life wandering round the Playboy Mansions in Chicago and LA, in his pyjamas and slippers, pipe in mouth, a bottle of baby oil in one hand, a Pepsi in the other. He was a very late riser, eating the same breakfast, prepared by Cordon Bleu chefs, every day; likewise the same dinner every night, fried chicken, prepared exactly to his specifications. He liked board games, pinball and movies, which seemed to take up most of his time, when he wasn’t working on the magazine, hosting parties or shagging. He favoured bosomy, blonde, leggy girls between the ages of 18 and 22. He didn’t seem to like them terribly bright and was quite forthright on the subject, explaining that if he wanted to have a serious conversation with someone, he had plenty of men friends around to chat with.

The so-called Bunnies, by and large, seem to have liked ‘Hef’. He appears never to have bullied any of them into having sex with him. Some of the women from the Playboy Mansions or Clubs have gone on to serious careers in the arts, government, higher education. One of Bill Clinton’s initial picks for attorney general, Kimba Wood, was shot down in part because she’d once worked as a Playboy Bunny, which seemed unfair even at the time. Gloria Steinem published ‘A Bunny’s Tale’ in Show magazine in 1963. She portrayed the Playboy Club as a demeaning, exploitative work environment. But Deborah Harry thought that ‘being a Bunny involved a rare combination for a woman in the workplace – beauty, femininity, sexuality, and at the same time, ambition and intelligence.’ Lauren Hutton described the Bunnies as ‘pre-feminist pioneers and extraordinarily brave for their time … We were like sisters learning together how to take charge of our own lives.’

In 1969, Steinem interviewed Hefner for McCall’s. She pointed out that his girlfriend Barbi Benton was ‘so young’. And young she was, just 18; Hefner was 42. Later, a wounded Hefner asked friends, over and over, why Steinem had to say that about Barbi; why couldn’t she have just used the word ‘fresh’? Steinem told Hefner during the interview that ‘there are times when a woman reading Playboy feels a little like a Jew reading a Nazi manual.’ The comment seems to have perplexed Hefner as much as it annoyed him.

Hefner and Benton were finished as an item by 1976, but not before he’d turned up in a limo and a white suit with Barbi on his arm at his daughter’s graduation from Brandeis in 1974, upstaging the commencement speaker, another Chicago celebrity, Saul Bellow. Christie Hefner, aged 23, a year younger than Barbi, who’d graduated summa cum laude, had reconciled with her long-absentee father on a visit to the Playboy Mansion only the year before. Six years later he put her in charge of the foundering Playboy Enterprises, a position she held until 2009.

As well as Mr Playboy, Steven Watts has written biographies of Henry Ford and Walt Disney, both Midwesterners like Hefner, and both, unlike Hefner, brilliant, visionary monsters. There was nothing especially monstrous about Hefner. And though he was an astute, risk-taking, hard-working magazine man in Playboy’s early days, there was nothing brilliant or visionary about him. The idea for Playboy came directly from Esquire, the magazine young Hefner most revered and for which he briefly worked. Esquire, at least in its heyday under Arnold Gingrich, was a literary magazine with a few sexy photos, directed at the ‘sophisticated’ adult male. Playboy is a porn mag with a bit of literature for cachet, directed at the wanker who would like to think of himself as sophisticated. In 1969, Rollo May argued in Love and Will that Playboy reflected a ‘new puritanism’ and a repressed anxiety among American men about impotence and intimacy with women. ‘You see a strange expression in these photographed girls,’ he wrote: ‘detached, mechanical, uninviting, vacuous … Playboy has only shifted the figleaf from the genitals to the face.’

Hefner, at heart, was a small-time provincial and the worst sort of parvenu. A poster-child of arrested development, he was a shameless exhibitionist and boaster, who kept a detailed log, many volumes long, of his every sexual encounter. From the beginning he was in thrall to a rube’s notion of Jazz Age glamour, craving to mix with and be thought well of by the famous and well-born. He was the happiest, richest, oldest 14-year-old jerk in America.