To The Penthouse In The Sky: Hugh Hefner, 1926-2017

Hugh Hefner, who once hosted a TV show called “Playboy’s Penthouse” in which he talked about Ivy League suits before becoming a full-time pajama wearer, has died at the age of 91. He will be remembered for many things, chief among them the association of pipesmoking with promiscuity.

Here are Ivy Style’s posts on Hefner and related themes over the years:

Golden Brush: Playboy Illustrator LeRoy Neiman

I Like Jazz, Ivy League Clothes, Gin And Tonic And Pretty Girls

Jazz, Foreign Films, G&T And Pretty Girls

Penthouse Sereade: Hef On Ivy, 1960

Pipes And Cardigans Get The Chicks

City Folk

The Great Indoors

Sex Education: A Playmate At Dartmouth

Hefner is either now with a bevvy of buxom angels for having liberated prudish America, or burning in hell for all eternity. Or he’s just dead. People have different opinions, including that Playboy was just a nudie mag. — CC

43 Comments on "To The Penthouse In The Sky: Hugh Hefner, 1926-2017"

  1. Carmelo Pugliatti | September 28, 2017 at 10:26 am |

    “Ivy” heyday was in 50s-60s (until 1967).
    Playboy heyday was above all in 50s-60s…so “Ivy and Playboy share the same age as cultural apogee.
    Hefner’s magazine could not consider the “ivy” trend in clothes.
    Said this,is Hugh Hefner and Playboy “Ivy”?
    I think no,
    The ideal clothes of “Playboy man” are more rat pack or italianate “continental”,or if you prefer,with a today definition “Mad Men”.

  2. Quite a write-up in the Times, touching on his sartorial descent.

    “After half a century of Mr. Hefner in pajamas, men have followed his lead into a careless uniform. The costume of T-shirt, jeans and hoodie expresses the ease with which many fellows can slip through life in 2017. They go from the couch to the office to the couch to a date. After Hefner, the clothes on the floor make the man.”

  3. Nobody’s ever going to say that Hef “is in a better place now.” (an oldie but a goodie)

  4. Beautiful Paul!! Heaven on earth.
    Rest In Peace..

  5. I had said that he would be maligned as the ultimate misogynist when he finally died, I was wrong. In the initial coverage of his death, he was portrayed as a trailblazer in the sexual revolution. There was even a quote from his where he said something like “we must preserve what we fought for in the sexual revolution.” Lest we forget that he only dressed in Ivy style because it was then in fashion and quickly adopted the modern Continental style when it became popular.

  6. I don’t really associate Hef with pajamas, but toupes, gold chains, and Gucci bit loafers. Mr. Hefner never modeled for Gucci, but if he had not been a magazine publisher, he would have been in Gucci ads.

  7. Marc Chevalier | September 28, 2017 at 1:12 pm |

    There goes the last sexual spark of the Cold War generation.

  8. Hefner is either now with a bevvy of buxom angels for having liberated prudish America, or burning in hell for all eternity. Or he’s just dead. People have different opinions, including that Playboy was just a nudie mag.

    Oh, dear. Cancel that subscription to nut-job Jordan Peterson immediately and make your mind up.

  9. “Pipes and cardigans get the chicks”–boy. talk about being on the wrong side of history!

  10. Mom: “Look what I found tucked under your son’s mattress.”
    Mom lets Playboy centerfold of Ellen Michaels, Miss March, 1972 unfold.
    Dad: “Hey, so that’s where it went.”
    Me: Double trouble.

  11. Carmelo Pugliatti | September 28, 2017 at 7:56 pm |

    The Vargas girl on Esquire free prudish America much more that Hefner,
    Said this i hope that he not “burning in hell for all the eternity”.
    Frankly i have ever I’ve always thought that is an exaggerated punishment.
    I think that in the Hefner case a pair of century in a harem of ugly girls is enough.

  12. Hef’s like Dorian Gray, minus the picture to take the brunt of his debaucherous lifestyle.

  13. Marc Chevalier | September 28, 2017 at 9:06 pm |

    Your comment hits below the belt, GS.

  14. But Carmelo’s is a knock-out!

  15. Hef’s hedonistic philosophy was morally repugnant, there’s no sugar coating that fact. M. Chevalier, if think Carmelo and I were “below the belt” check out this great piece by Ben Shapiro:

  16. Marc Chevalier | September 28, 2017 at 11:43 pm |

    GS, my comment was meant to be cheeky: hence its double entendre.

  17. @ GS.

    Reading Ben Shapriro I couldn’t stop thinking that Ben was protesting just a little too much. I wonder if Ben was also a late loser of his virginity?

  18. @MarcChevalier: is calling it “cheeky” a double-entendre about a double-entendre? A double entendre once-removed? A triple entendre?

    Shapiro is the poor man’s WFBJr., with a dose of finger-wagging yenta thrown in.

  19. I read somewhere that Hef’s hedonistic philosophy was a result of his first wife cheating on him. He said it was the most devastating moment of his life.

  20. Mac, he said he always felt as though the other guy was in bed with them. His wife even let him sleep with other women to make up for it. Probably why he never had a meaningful monogamous relationship again. There was a video of Hefner calling himself s hopeless romantic and that he could never find true love.

    Paul, I guess Ben is this generation’s WFB Jr. good point.

    Down Tradden, I believe I read that he too waited until he was married except his wife didn’t cheat on him like Hef’s.

  21. Carmelo Pugliatti | September 29, 2017 at 10:43 am |

    I think that the 1950s-60s Hefner is funny and smart in the same way of a old James Bond movie.
    Is “Mad Men” without drama and troubles,if you know what I mean.
    The 70s Hefner is sick and repugnant (but..hell… ALL the 70s were sick and repugnant).
    The 80s and following years Hefner was boring and senile.

  22. Hefner took a real nosedive in both popularity and his own health after the brutal murder of Playmate Of The Year 1980 and budding movie star Dorothy Stratten by her separated husband. Peter Bogdanovich, Dorothy’s lover and movie director, blamed Hefner and his hedonistic philosophy for her murder. Hef blamed the whole episode for his subsequent stroke.

  23. Below is a link for June Christy’s 1959 appearance on Hugh Hefner’s “Playboy’s Penthouse Party” tv special. The girls, the boys, the clothes, the smoking and the one and only June Christy singing a favorite. For me it all came together at this moment.

  24. “Shapiro is the poor man’s WFBJr., with a dose of finger-wagging yenta thrown in.” Yes, of course he is. But you haven’t addressed any of Shapiro’s arguments, only called him names. Hef spent half his adult life as a creepy old guy in pajamas running a squalid prison at the Playboy Mansion West for bunnies and playmates who expected a far more glamorous life than what they found there. And if anybody could be called out as the chief exploiter and objectifier of women in our lifetimes…

  25. Poison Ivy Leaguer | September 29, 2017 at 12:21 pm |

    Robert L. Green’s fashion advise in Playboy’s back to campus issues in the early to mid 60’s was pure trad.

  26. I’m trying and failing to think of someone who had more impact on America during the last 50 years of the 20th century than Hefner. Perhaps I’m forgetting someone, but my point is that he had an enormous amount of influence.

    Sure, we bought Playboys for the pictures, but we ended up reading some very important long interviews, fiction from some of the best writers, and thought-provoking non-fiction and criticism. Moreover, the magazine crusaded for the 1st Amendment, civil rights and numerous other causes for personal freedom.

    His personal life was certainly questionable, but that was just part of the story. It was his magazine that pushed the boundaries and broke the rules.

    Oddly enough, I once had the opportunity to deal with Hef’s personal assistant. He was very gracious and attentive in dealing with a my trivial matter. In my experience, the behavior of close aides usually reflects their bosses’.

  27. @GS: I’m happy to say that I know quite a few millennials who, like WFBJr. at his best, are witty and persuasive and thought-provoking without being scolds. Shapiro just isn’t one of them.

    @rojo: are you a young(er) person? I ask because, as with many things here, there seems to be a real generational fault line in the way CC’s readers view Hefner. And that’s good – it makes the conversation more interesting. As for Shaprio’s “arguments”, though, see my response to GS immediately above.

  28. Paul, I am a younger person (college student) and I enjoy Shapiro’s straightfordward, no-nonsense style. To those who disagree with his politics I guess he can come off as a “scold.”

  29. @GS

    I agree about Shapiro. Buckley was an intellectual who enjoyed debating and socializing with liberals. He raised the level of the conversation. Shapiro is merely a polemicist.

  30. @GS: if only it were that simple; writers of all political stripes can be scolds; but you have to be a good writer before you can be a good advocate.

  31. whiskeydent & Paul, both of you fail to counter any of Shapiro’s points against Hefner as if being a “scold” strips his argument of any credibility. I’m assuming one or both of you actually read the linked article because you’ve taken the time to insult the man at the very least.

  32. @GS: yes, that’s exactly correct – being a bad writer *definitively* reduces your credibility. And I’d say the same about Markos Moulitsas (Daily Kos) as I do about Shapiro: neither of them offer serious political thought.

  33. I rest my case.

  34. @GS: like Shapiro, you’ll have to do better than that in this crowd.

  35. Buckley could be pugnacious, but Shapiro is just straight-up disagreeable, Big Five-wise. Buckley would consider a dinner party an opportunity for witty repartee. Shapiro would consider it a battlefield.

  36. GS

    From “the media” to Madison, this article is a string of straw men connected with bitterness. Go watch the Buckley-Hefner debate CC put up. Both give their best and its illuminating. They get to the crux of the issue: does a Religious code rule us as individuals or do individuals rule themselves?

  37. Through all his theatrics, you get the impression that Buckley really wanted to deeply engage his conversational partners – including ‘opponents’.

    Another suggestion for young people: go watch a Milton Friedman lecture on YouTube. Also pugnacious. But undeniably thought-provoking. And never without wit and humor!

  38. Paul, to answer your question, without revealing my exact age, I will state that I am in my 50s.

  39. Come to thank of it, by the standard of those old enough to remember and have read Playboy in its 1950s to very early 1970s heyday, being in my 50s does make me a younger person.

  40. @Cort,

    Thanks for the link to Misty Miss Christy. As the clip opens, the tall blonde standing to our left is Janet Pilgrim, three time Playmate of the month in 1955-56. Real name Charlene Karalus, a clerk in the subscription department at Playboy. Said to have agreed to take her clothes off and pose as playmate in exchange for a new addressograph for the office. Hefner was claimed to have chosen the name “Janet Pilgrim” to make fun of sexual Puritanism.

    Janet Pilgrim continued to work at Playboy for at least the next decade, maybe longer, in the corporate offices; her name was on the masthead and Hef offered a personal phone call from her in return for a lifetime subscription. She recently passed away in CT, I believe.

  41. Hef was America’s biggest pimp. The way he treated the girls at the mansion was not good.

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