When he died on September 27 at the age of 91, Hugh Hefner was no playboy.  He was an old man trapped in what amounted to a factory, surrounded by silicone, plastic, and hydrogen compounds.  Playboy’s circulation had peaked 45 years earlier with its November 1972 issue.  Even before then, Hef’s magazine had long ceded its place as the imagemaker of the Sexual Revolution.  Its commercial zenith was also a sign that Playboy had gone mainstream—not because its revolution had succeeded but because it wasn’t so revolutionary at all by the standards of the Manson era.  Playboy published its share of “New Journalism” and middlebrow fiction, some of it quite good on its own terms.  But Hefner’s playboy image, a tasteless man’s idea of class, was already as dated as a daguerrotype.  The real revolution in sex had been pharmaceutical, not pictorial.

If Hef had somehow held onto his youth, he would still have been a fossil.  But of course, he didn’t: He lived to be a septuagenarian, octogenarian, and finally nonagenarian doddering around in a museum-piece 1950’s smoking jacket.  He was a ruin of a man, a nasty Peter Pan who couldn’t grow up to enjoy adult pleasures, as opposed to adolescent ones.  A woman who worked for Hef’s magazine a decade ago reports that what passed for sybaritic delicacies in the fabled Playboy mansion were bowls of Lay’s potato chips.  Hefner’s taste in women was hardly more refined: He surrounded himself with the sort who relied heavily on peroxide and plastic, bleached to the roots and structurally reinforced about the upper chassis.  It’s as if someone described to a epicene what a red-blooded man was supposed to like, and Hefner obliged.

Hef made millions and bedded Barbies, but the pornographic brand that was his life’s work might just as well have been another 20th-century department store.  He thought he was selling a lifestyle, when what consumers really wanted was ever cheaper satisfaction—Walmart, not Sears or Playboy.  It isn’t at all true to say now, though, that the Internet has done to porn what it did to retail.  What the Internet has actually done to the market Playboy once thought it could serve defies the laws of capitalism: The industry’s “goods” have been so debased by oversupply that buying and selling is unsustainable.  Thus, Playboy tried out a no-nudes policy last year, which unsurprisingly didn’t rekindle the magazine’s fading mojo.  Sex might be too cheap to sell, but that hardly makes a sexless porno mag any less of an imbecility.  The industry’s screen stars have had a little more success reinventing themselves—they’ve begun decamping to Hollywood, where, to be sure, they risk winding up in an even more unwholesome environment than before.

Hefner’s admirers and critics, the former largely composed of Baby Boomers for whom Playboy once meant something personally, have overstated his importance, treating him as what he imagined himself to be: the kingpin of lust, daring liberator of uptight America.  He happened to exploit the right market niche at the right time, and he got rich—though nowhere near as rich as he liked to pretend.  Fortune calculated that at the time of his death, Hefner was worth about $26 million, according to “a generous back-of-the-envelope estimate.”  Would it surprise anyone to hear that divorce and “dating” (a man Hef’s age wasn’t getting by on charm, and Hef never did anyway) ravaged his finances?  Hefner was not the CEO of the sexual-industrial revolution but at most a middle-manager, if not just another cheated employee.

The libertines an era produces speak volumes about it.  Hefner was the 20th-century McDonald’s-style libertine, his idea of sex as sophisticated as a Happy Meal.  Casanova was a man of intrepid travel.  The Earl of Rochester was a wit.  Hefner was for a few years a successfully marketed mid-century product; then he was an undead echo of his own fleeting fame.  And now he is dust.

He remained to the end useful for moralists’ and feminists’ target practice, but it’s worth taking a moment to consider Hefner in a simply existentialist light.  What does it mean to live according to one’s own values, when those values cannot provide any vision of flourishing beyond the age of 40?  For over half of his life, Hefner, judged on his own terms, was in steep decline: less attractive, less potent, less significant in business and popular culture.  There was no place for contemplation in his life—not in any serious sense.  He had to be what he was and who he was through action—yet he was incapable of acting. His celebrity was parasitical from start to finish: Playboy began with purloined Marilyn Monroe nudes, and to cling close to fame in death, Hefner bought a cemetery plot adjacent to hers.  He is now interred in the mausoleum of Los Angeles’s Westwood Memorial Park.  But for half his life he was already his own Playboy mausoleum.