Hugh Hefner himself is not that important, but the importance lies in how America looks at Hefner and Playboy brand. For all purposes, Hefner is not someone special, and therefore that's the secret to his visual success. He knew how to tap into that world that was his generation. Also, his other great secret or talent is that he wasn't hip whatsoever. His Playboy philosophy appealed to the most unhip part of the population. He didn't make the female an object, but more that he's part of the world that allowed or projected that world in a glossy magazine. I think his appeal is that he was able to communicate with the average Joe and tell them that they too can be part of this world. The big difference between Trump and someone like Hefner is that our President doesn't want anyone to be part of his class or share the power, on the other hand, Hefner clearly wanted to express that you too can be in his place.
Playboy was the only world where Herb Albert can beat out Miles Davis as the best trumpet player in one of the Playboy jazz polls. This, I think expresses honestly what the Playboy Magazine thinks and listens. It's an image that has no bearing on reality, yet, it is a remarkable skill to make a world of one's liking. When Hefner was younger, it was awesome-like, but as soon as age creeps up on one, it becomes bad taste. In fact, there is a lot of kitsch culture that goes with the Playboy brand and image. They didn't intend it to be in that light, but alas, they were not that self-aware of their existence.
"The Last of the International Playboys" is a truthful portrait of that generation of lost men. The aging swinger was grasping toward youth, and not be able to hold on to its magic - in fact; it causes premature aging! Hefner was never really young. He was always an old man, and if anything, it's his brilliance to capture the middle-aged American Male's psyche in the mid-century era. - Tosh Berman