Fun fact:
Jerry Buss always wanted to be him.
Buss not only lived a similar lifestyle to Hef in some ways, but he tried really hard to become Hef's friend.
Hef wasn't really interested in hanging out with him, and the two maintained a cordial but mostly distant relationship. Buss did attend a few Playboy Mansion parties, and Hef went to a few Lakers games as a guest of Jerry's, but there was no real friendship.
When Hef was interviewed in 2013 following Buss' death, he stopped short of calling Buss a friend: https://deadspin.com/5986042/hugh-he...ers-jerry-buss
One interesting fact about the Playboy Mansion that some people don't know is that it was frequently rented out. Most "Playboy Mansion" parties did not feature Hugh Hefner, nor were they associated with Playboy, nor were the girls in attendance usually Playboy models.
This was true of the infamous "Playboy Mansion poker charity tournament", which Jennicide helped promote at one point. Jennicide was probably the closest thing to a Playboy girl they had there. In that embarrassing tournament, they ran short of time, had to abruptly cut it off, and a then-unknown Terrence Chan got screwed out of a WSOP Main Event seat by an also-then-unknown Joy Miller, who was running it.
None of this was Hef's fault, of course, because he was simply renting out space in the mansion to whomever paid.
But if you hear people brag to you that they "partied at the Playboy Mansion", keep in mind that there's a good chance they simply attended a party put on by a third-party company which rented space there for a few hours.