VEGAS – May, 2004

A Date with Hef at the Playboy Mansion

The legendary publishing icon talks about his five girlfriends, life inside his party house, and his latest effort, Hef’s Little Black Book

By Anna David

As I wait for Hugh Hefner, I sit on a sofa below a table that holds both a bust of Barbi Benton (his girlfriend during the late ’60s and early ’70s) and a framed photo of Kimberley Conrad (his wife from 1989 to 1999). It seems quintessential decoration for the icon who has managed to avoid mundane issues such as fidelity with the kind of aplomb that makes most men quiver with jealousy.

The weather can best be described as the kind that makes a rainbow seem inevitable – bright and sunny one minute, cloudy and stormy the next. It is, Hugh Hefner will smile after he hears a crackle of thunder, “a great night for a murder.” Though it’s early afternoon when he says it – and he is, quite clearly, joking – it does make me realize how interchangeable day and night must be when you’re pajama-clad 24-7 and the world, at the age of 78, is still an adolescent male’s fantasy brought to life: beautiful, buxom blondes, games, movies, delicious food and a mansion as iconic as the man himself. Then again, “a great day for a murder” just doesn’t have the same zing to it – and Hefner is a man who knows his zing.

Officially, I’m here to talk to Hefner about Hef’s Little Black Book (which is due out this month from HarperEntertainment) but in actuality I want to discover as much as I can about a man who, rather than playing down his own quirks to fit into the world better, has simply created a world that caters to those quirks. If you don’t believe me, try to explain the fact that certain designated Mansion activities have occurred on the same night every week for decades, the Frankenstein monster bust or Buck Rogers framed rocket gun you might find next to a big old bottle of baby oil in his bedroom or the fact that Hef has always had eggs, bacon, hash browns, toast, applesauce and a glass of milk after sex. The man has made a lifestyle out of nearly ritualistic repetition of pleasurable acts.

As luck would have it, Hef’s book tackles these topics and more – and the man himself seems game to answer just about everything. I start off slow, initially too intimidated to broach the topic of sex – even though I realize that’s like being afraid to ask a priest about God.

In the book, you talk about how you reinvented yourself as a young man. What were you like before?
Well, I was raised in a typically Midwestern Methodist house with a lot of repression and my dreams and fantasies all came from the romantic music and movies of my childhood. Because I was raised in a house where there was not a lot of hugging and kissing and showing of physical emotion, I escaped very early on into fantasies.

How long were you able to live in a fantasy world?
Until the period right before I was going to get married when [my first wife] Millie told me that she was having an affair. Nothing could compare in terms of devastating things. At that time, I was a romantic innocent so I was totally unprepared. It wasn’t real for me.