The Playboy Mansion symbolized the hedonistic dreams of my generation, and I wanted to look cool. : Notes on the Last Playboy

It occurred to me as I drove up the sweeping driveway to the Playboy Mansion that my shoe had a hole in it. The realization hit me just as I passed a sign that said “Brake for Animals” and came into sight of the baroque castle that is the centerpiece of Hugh Hefner’s pleasure park.

It was too late to do anything about the shoe, of course, because a red-jacketed valet was opening the car door for me even before I came to a halt, and I couldn’t slam it shut again and peel out like a madman. For one thing, a Rolls was blocking my Plymouth’s path.

Normally, something like a hole in my shoe wouldn’t bother me much. I’ve kicked around long enough to know that if anyone is going to judge me, they’re going to judge me good or bad long before they get to my shoe.

But this was different.

Hugh Hefner, bunnies and the Playboy Mansion symbolized the hedonistic dreams of my generation, and I was at long last coming to the mecca of Miss October. Above all, I wanted to look cool, but you can’t look cool with a hole in your shoe.

I sighed and, accepting my unavoidable state of dishevelment, entered the mansion itself. I felt like Colombo at a White House reception, bumbling about in a raincoat at a party that required white tie and tails.

The reason I was at the mansion in the first place was to attend a press conference having to do with the 10th annual Playboy Jazz Festival that will be held in June at the Hollywood Bowl.

I have nothing to do with jazz and I’m not sure why I was invited to the conference, but I went because it afforded an opportunity to look at the mansion and maybe at one of those centerfold women who dance like dolls through the erotic fantasies of the young. Pubescent dreams die hard.

The conference was held under a plastic awning in a courtyard that looked out on cultured gardens, a waterfall and birds. I think they were flamingos and macaws, but I’m not sure. One gleaming-white, parrot-appearing bird sat on a piece of driftwood and bobbed continuously throughout the press conference, providing a kind of hypnotic counterpoint to the whole thing.

Al Martinez

I felt as though I were Pinocchio and had stumbled into a strange and uneven carnival of ultimate pleasure and would surely pay the price for peeking even this much through a forbidden window. Good judgment yelled Run! but endless fun is a powerful lure, so I stayed to play, poor Pinocchio.

There was food and booze to keep us busy and cool jazz from stereo speakers as we stood around waiting for something to happen. I drank coffee and watched, observing an era at its last party.

The men seemed to know each other and engaged in small talk, while the women journalists, aware of their presence in a castle where the perfect breast and the ultimate behind are proud logos, fidgeted nervously and felt tawdry. I sat on a wooden chair in such a manner that the hole in my shoe wouldn’t show, though sometimes I forgot.

Eventually I said to hell with it, and let the foot fall where it may.

Only about a third of the chairs were occupied when Hef strolled in with a woman on each arm. One of them was Jessica Hahn, the Jimmy Bakker plaything who had come to the mansion to find Jesus, and the other might have been Kimberley Conrad, Hef’s newest personal bunny.

Jessica was dressed in modest gray, but the decolletage that reached down past her navel defeated any notion of piety she may have been trying to project.

I believe the second woman was Kimberley because it was on her that Hugh lavished his attention. I watched as he mugged and giggled, appearing old and silly in his giddiness, the last Playboy trying for one final glory.

He drank Diet Pepsi through all this, and it struck me that the man who could have anything wanted the drink that epitomized youth, which too was a kind of testimonial to his fading spirit, blending the nectars of sex and springtime in a sugar-free world. Poor Hugh.

Then satirist Mort Sahl came on. Mort was there because he’s going to be emcee for the jazz festival. I can understand loving jazz and making a few bucks and needing an audience (Don’t we all?), but somehow Mort Sahl performing at the Playboy Mansion is the social equivalent of Alex Haley waiting tables at a white supremacy rally.

You don’t end up serving the enemy even if he is only a symbol. The Mort Sahl I knew 30 years ago in North Beach would have taken Hef apart. But maybe that’s the point of all this, of going to the Playboy Mansion in the first place.

Maybe it simply doesn’t matter anymore because the era has locked arms with the feminists and marched on by, which is all right with me. Hugh Hefner and Miss October were becoming boring anyhow, and the whole thing probably wasn’t worth it after all, poor us.