There was a very long-running series of essays called The Playboy Philosophy that caused quite a fuss in the day... HH was/is? a fairly good writer and he was able to hold interest. To a non-American, it was rather startling to discover how doing one thing, legally, with your wife in State A could get you jailed if you did it in State B. It put me in mind of my m¡serable time in boarding school, a prison school run by missionaries. I think becoming a fashion/calendar photographer was my tiny act of vengeance.
The magazine used to feature Vargas (pin-up painter) as well as a 'modern art' maestro whose name I can't recollect at this time of night. The only thing that felt (to UK eyes) a bit flat was the male fashion: trousers too short, shoes too heavy... oddly enough Hollywood seemed to get it right far better! I think Playboy fashions sometimes tried to ape what was going down in Carnaby Street during those 'Swinging London' days, which was impossible - it was in a state of perpetual change whilst it lasted - hardly possible to copy. Also, it didn't fit the American image, Not in the days of the Beach Boys, at any rate!
Rob C