I’ve read the actual book they’re talking about there, as well as a few others like it. The one thing that is made clear by every author (they are all ex gfs) is that while things are tightly controlled and there are rules to the Mansion, you can leave when ever you want, you are never forced to do drugs, have sex, etc if you don’t want to. So, I guess my take on it is: the women know the rules of living there and if they want to, that’s their business. Woo! Feminism.
IMO, the OP is looking at this the wrong way: being “cool” has NOTHING to do with being a decent/nice/intelligent/good/whatever guy. In fact assholes are much better at being cool.
FWIW: if you can walk around in pajamas all day and people accept it, you’re cool (or demented). Still doesn’t mean I have to like him. I’m not in high school, after all.
Hefner is cool because he doesn’t care what everyone else thinks. He’s living the life he wants to live.
There might have been a plausible alternative for him as a young man, but the time was ripe to make a killing flouting conventional morality. If there were a plausible alternative for him as an old man, I can’t think of it.
Figured he’d had enough homage and luxury and orgasms, and go live atop some mountain? Maybe the thought crossed his mind, but then they invented Viagra.
Yes, that is the person I meant. I didn’t realize there was another well known Hugh Hefner, but to clarify, I was talking about the founder of Playboy.
I also find it incredibly sad when people instantly equate being wealth with being enviable. It just breaks my heart.
Why? If I had more money I’d be exactly the same as I am now but I’d have more money and therefore be better able to supply the needs and wants of my family. What’s not to like?
A few million might be nice, but if I had to turn into Hugh Hefner to get it - so not worth it.
I think he’s kind of sad actually.
I think this excerpt from the works of one T. Pratchett sheds some light:
Hefner is cool because he does it his own way and doesn’t give a crap what anyone else thinks. That is an admirable way to live.
Well, he sounds like he’d be a lot more fun to be around than the OP. 
Seriously, though, if it makes you feel better I don’t, personally, hold Hefner up as some sort of cultural touchstone whose lifestyle I want to emulate in every detail. OTOH, it’s not like Hefner invented the concept of women using their attractiveness to social advantage, and as others have mentioned the women who go along with his self-designed fantasy life appear to do so willingly and enthusastically. Hell, I know more than one woman who sincerely believes that being put on display at a Playboy Mansion party would be a high point of their lives. Not how I’d approach things, but if that’s how they want to live the dream, eh, go for it. As negative aspects of current society go, it’s fairly unimportant.
In conclusion, lighten up, Francis.
Hef is cool, or rather, he was cool and hip, as in hip cat, when being a hip cat was cool; and he banked enough cool hip cat credits for the first 20 years of Playboy that he has been able to coast on them for the last 30+.
He did seem at some point to be fading, but then like some other surviving icons of his age, he had a sort of comeback in the '00s by Shatnerizing into a living self-parody; however he seems to be happy and comfortable with living as a self-parody, as if entirely non-ironic about it, and seems in no hurry to also get himself a more 21st-century-like gig.
However may have lacerated his old-school hipness cred by seeking new-school hip cred through becoming part of “Reality TV”. Thanks to The Girls Next Door many people saw the old image of “Hip, With-It Playboy and Entrepreneur” (which already to many was only an obscure retro reference) replaced with that of “Millionaire Dotty Octogenarian Sugar-Daddy”.
Still, if some dude who had achievements in his past is now doddering and ancient and wants to spend his last years on Earth carrying on like a fool at his own expense, who am I to diss him for it? Similarly if some young hottie wants to bank on the hottieness while she’s got it. God bless him and the girls, all the same.
Not to further hijack the thread, but couldn’t you have just not used those words if you didn’t want to use them?
You just lost me there. Hef is the embodiment of the Playboy philosophy/culture/lifestyle. How can you have a problem with one but not the other?
Of course men see us as sex objects. Big deal. I look at sexy men too. Re Hef, he makes a mockery of himself but he’s earned the right. Misogynist? no.
Absolutely true. Several years back, I interviewed for a position at Playboy as a web developer. I got called back twice - ultimately I chose not to work for them as the job was not at the cool building off Mag Mile but out in the burbs.
Every single person who interviewed me was a woman. It was the most female-centric workplace I have ever seen this side of the Michigan Womyn’s Music Festival.
Part of that may have been due to Christie Hefner, the former day-to-day Editor, and part may have been that they told me they had difficulty hiring men due to the “girlfriend/wife factor” - apparently a large number of men have SOs who would object to them working in daily proximity to beautiful and often unclothed women.
There was a time in the 60’s, 70’s and into the early 80s that Playboy was cool. Honest to God cutting edge, socially relevant, great writing cool, and Hefner was cool along with it. Times have changed and Playboy is kind of self parody these days, as is Hefner.
The plausible deniability and innocence of the Playboy lifestyle are gone and the Playboy girls these days are pretty much wall to wall silicone bimbos who could as easily been high priced call girls as bunnies.
But there was a time when he was cool, even if he is joke now.
Diosa- you had to know that was coming. After all, a lot of us have seen your pic! I just wasn’t going to actually say it.
Now to the OP- I have a lot of problems with what Hef has released on society, the Playboy philosophy of non-committal sex; the gradual contempt for the traditional, self-discipline & spiritual values; the celebration of the vacuous- and I have no problem believing the reports that there is an emotional emptiness or disconnect between him & the people around him, including his younger child(ren?)…
but man, was he cool.
Three words- Playboy Jazz Festival.
Yeah, I get the same feeling. I remember reading a comment made by a former employee of Playboy (Arnold Morton) calling Hefner the “sweetest, most selfish man I’ve ever known.”
He would almost have to be somewhat distant emotionally because his whole life is geared to suit him to a tee, and he absolutely will not allow anyone or anything to deviate from what he wants to do or when he wants to do it. He affable and generous with his friends and girlfriends but is in total control of absolutely everything that happens in his life, when it happens, and with whom it happens. Everything he eats is prepared just so (for example, his chefs have to pick out whole potato chips from the bag as he doesn’t like to be served broken ones); every song played on the Mansion sound system is approved by him; the activites that take place, when they take place and how long they last are dictated by him; the movies everyone watches are selected by him, etc., etc., etc.
Like someone said upthread, he does what he wants and he doesn’t care what anyone else thinks about it. You have to be somewhat emotionally distant from people in order to live your life that way and force everyone else either to go along or get along, and I imagine this extends to family and intimates as well.
And then there is the nature of his relationship with his multiple bedmates. I’ve read comments written by one of his former bedmates that he lives in something of a fantasy land when it comes to the girls in his life - convincing himself that all is harmony and love between them and that they are all, in a real sense, “family” - when the reality is that the girls barely get along and backbiting, bickering and jealousy are the order of the day. Plus most of the girls don’t love Hef, even though they do generally like him. So there’s a disconnect there as well.
Still, he’s a personable guy and well-liked. He’s just insistent about every little aspect of his life and won’t deviate - or allow anyone else to cause him to deviate - from them. And besides, this all has to do with his private, in-house life and doesn’t really pertain much to how he’s perceived by the public at large and other questions posed by the OP.
I used to think there was some misogyny in Playboy. Not that that stopped me from, umm, reading it for the articles. When Playboy came to my college campus for one of those “girls of college campuses” things they had a line over four blocks long of women wanting a chance. Hundreds, maybe a thousand women willing to wait in line for that long for a chance to make a few bucks by having their picture taken in Playboy. Maybe I was mistaken. The alternative it is to believe that there is something wrong with most women, which is misogyny itself, no?
You have to remember in the context of the 70’s and early 80’s being in Playboy, when Playboy was cool, was kind of a social coup for a lot of women. There was a huge level of admiration, almost worship, of Playmates. It’s not like today when you have D list celebs, plastic surgery celebrity freak shows, or aging actresses posing. It was a big, big deal for a woman to be a Playboy Playmate.