There are days (or entire decades) when Hefner greets the midday sun in silk pajamas and a robe, but on this particular afternoon, well, the playboy just wasn't in the mood.
Hefner had arrived back at his 29-room mansion after attending the funeral of Bettie Page, the pin-up queen, and he was still wearing his mourner's jacket as he sat and sipped from a bottle of Diet Pepsi in the hush of a downstairs library.
Hefner considered Page a friend and fellow pioneer of sorts on the old frontier of American sex culture.
Now, like so many others in Hefner's long journey, she is gone.
"We knew it was coming, and there comes a point in the illness . . ."
His voice trailed off and then, adjusting his gold bunny cuff links, he smiled.
"We're not really talking about Bettie Page here today."
No, but the legacy of desire - as well as the desire for legacy - are core concerns for Hefner these days.
He has arguably never been more famous, but the glossy centrefold citadel of his empire, Playboy magazine, has struggled, and Hefner (82) seems most at ease talking about the past and his consuming passion - no, not that one.
According to Hef, Hollywood was his first true obsession.
"Everything I learned about love, I learned from the movies," Hefner said.
"The reality is because I was not shown affection, I escaped into an alternate universe, and it came right out of the movies. Love for me is defined almost exclusively in terms of romantic love as defined by the films of my childhood."
There's a strong chance that Hefner finally will see a version of himself as a child up on the screen; a biographical film is planned and, according to Hefner, production could be under way in the next few months.
Brian Grazer is the producer and Robert Downey jun is keenly interested in the starring role.
"The one thing I would want the film to be is something other than a light comedy, to have something to say and express something about the change in social sexual values.
"You know, Brian made a comment that I was the only man who had made love to over a thousand women and they all still liked him. And I do take some pride, in fact, that I remain friends with the majority of former wives and girlfriends. I am a romantic."
Perhaps, but this is the graceless age of internet porn, and Hefner's magazine, which celebrated its 55th anniversary last year, has been receding, and Hefner's lifelong fascination for film is moving up among his priorities.
The biopic will be co-produced by Playboy's Alta Loma Entertainment, his production company, which is redoubling its efforts in Hollywood.
After years of making soft-core porn, the company was a limited partner in August's The House Bunny, a racy but PG rated farce.
Alta Loma is following that with the R-rated Miss March, a comedy about a guy who wakes up from a coma to find his girlfriend as one of Hefner's playmates.
There's also talk of a live-action version of Little Annie Fanny, the air-headed and bubble-breasted Playboy comic-strip character created in 1962 by Mad magazine alums Harvey Kurtzman and Will Elder.
If it all sounds sophomoric, well . . .
Hef, like his magazine, has a penchant for flipping between cartoon lewdness and lofty parlour-room pursuits.
For decades, movie screenings have been a tradition at the Playboy mansion.
Hefner used to screen two new films every week but, in the 1990s, he surrendered to the fact that the contemporary cinema output just doesn't yield 104 good movies a year.
Now, Friday nights are for new films,while Sunday nights are for the classics.
The Playboy mansion and its master have become symbols of refined debauchery, and Hefner has carefully cultivated that imagery.
The Girls of the Playboy Mansion, an E! channel show that brought cameras into the mansion to record Hefner's relationship with a trio of curvy blond girlfriends, began its fifth season last October.
A sixth season is on the way.
There's also Mr. Playboy: Hugh Hefner and the American Dream, the biography by Steven Watts, who was given unrestricted access to the tycoon's vast archive of self, which includes journals and scrapbooks dating to his youth.
The library shelves are dominated by books on Hollywood history, and it's surprising, perhaps, that Hefner hasn't put himself in their pages in a bigger way since moving west in 1971.
Like Howard Hughes, he could have bought a spot in the dream factory, but Hefner has mostly been content with just watching.
The great exception to that was his unlikely role as a key producer for Roman Polanski's grim and gory 1971 The Tragedy of Macbeth, the director's first film after the 1969 murder of his pregnant wife, Sharon Tate, during the Manson family attacks.
"It was a fascinating film, flawed but fascinating. It was directly related to the murders. It was such a dark and cathartic project. I only wish I had produced his next film, Chinatown."
