At 73 Hef is dating college-age twins (Sandy and Mandy) as well as another young woman (Brande) and a fourth (whose name doesn't rhyme). He starts telling us about how the twins had never been to Disneyland, then goes off on a tangent about staying in touch with the passions of youth. And for a minute — even though this is Hugh Hefner sitting here in pajama bottoms and we're surrounded by nude portraits of his estranged wife and even though we were just talking about the great group-sex parties of the '70s and the man had stopped for a second to clarify that he was “not an eccentric” and then had laughed weirdly — he seems to be channeling the spirit of Walt Disney. Quietly he asks, “What kinds of dreams did you have when you were a kid, and what's the grown-up version of that?”
This is a message of a half century of sexual wisdom. And it is oddly comforting and mesmerizing. He nearly whispers, “Hold on to your dreams and don't be confused by what everybody else tells you you ought to be doing.” There is a cuckooing of exotic birds outside, and you can almost hear Jiminy Cricket piping up: If your heart is in your dream, no request is too extreme.
"The Road To Boobville" by Adam Sachs, GQ, December 1999. My thoughts on Hef are here. Ebert, on the other hand, is a little more smitten.