Playboy After Dark

"What I have here is really an extended family of friends," says Hefner. "It's a wonderful way to live your life, because for too many adults, once you're out of your childhood and school years, you don't have that little gang of friends that you can really share things with, and it enhances your life immeasurably." His friends testify to Hefner's affability, generosity and fondness for good company. Tuesdays are often family night screenings, with Hefner's ex-wife, Kimberly Conrad, and their two sons, Marston, 14, and Cooper, 13, coming over. (They live in a house adjacent to the estate.)

There's often a celebrity contingent as well--Jim Carrey, Elizabeth Taylor, Kevin Spacey, Mark Wahlberg and Roger Ebert have all been in attendance--and many were there before they became celebs. "Thora Birch practically grew up here," says Hefner, and a pre-stardom Sharon Stone was a Sunday-movie regular. But it's Mondays that can get pretty ribald. Started when some of the men's wives initiated a weekly girls' night out on the town, "manly night," as they call it, "is kind of like Saturday matinee," says Hefner. "That's when we run the more inconsequential films and the B-movies, the things we enjoyed when we were kids, and that's the one [night] where the guys nominate and vote on what they want to watch." (Hefner's personal film archive numbers over 4,000.)

Though Hefner could easily have constructed a separate, palatial private screening room on the property, he kept things cozy by refitting a first-floor living room in the mansion with a motorized 9 × 14-foot screen that descends from the ceiling. A Miró and a Picasso (a large nude, appropriately) adorn the room, which also has a fireplace, a large vanity mirror, a deluxe chess set and a piano; a walk-in vault at the back of the room became the projection booth.

But Hefner's appreciation of film goes far beyond the mansion walls. Over the years he's donated thousands of dollars to the UCLA Archives and the George Eastman House for film restoration; funded documentaries on early filmmakers and actors, including Mary Pickford, Lon Chaney, Marion Davies, Clara Bow and Frances Marion; and underwritten at USC's School of Cinema-Television a course on film censorship (Hefner stops by each semester as a guest speaker). Hefner even spearheaded a campaign to restore the famed Hollywood sign back in the '80s, concerned about a sense of history lacking in the heart of movieland.

Hefner, born in 1926, notes that he came along at the cusp of the sound era; it wasn't until later that he discovered--and became captivated by--silent films. Though Hefner declines most invitations to movie premieres around town ("I'd rather watch them here," he says), he does step out with the gals for an event like a live orchestra-accompanied screening of the silent-era landmark Sunrise at one of the opulent former movie palaces downtown.

Playboy magazine and Hollywood, in fact, have had quite a mutual influence for decades now. Stars like Jayne Mansfield, Kim Basinger and Pamela Anderson jumpstarted their nascent acting careers with Playboy pictorials, and Playboy produced a number of theatrical releases through its Alta Loma production arm in the 1970s, including Peter Bogdanovich's Saint Jack and, most notably, Roman Polanski's film version of Macbeth. In recent years, the company has focused on its adult TV productions, but recently Playboy announced it was reviving Alta Loma to produce theatrical releases. And Hefner's remarkable life story may become a movie itself, produced by Brian Grazer; the project is currently in the script stage. "I understand Johnny Depp has expressed interest," says Hefner. "That would be very interesting. He's a fantastic actor."

But perhaps most emblematic of Hefner's affection for Hollywood is his purchase of the vault next to Marilyn Monroe's in Westwood Memorial Cemetary, minutes away from the Holmby Hills mansion. "Yes," he says, smiling at the thought, "I will sleep through eternity with Marilyn Monroe." She was Playboy's first cover model, but Hefner never met her--though he does feel a deep connection. "We were born the same year, 1926. She would be celebrating her 78th birthday if she was alive. She was very much influenced by movies as I was, [for her] an escape into dreams from a more troubled childhood."

Hefner can talk movies with the most rabid of movie buffs--he eagerly digresses into the history of the Production Code, the largely immigrant foundations of the Dream Factory, the current state of independent film--but he has other interests, too. Post-screening, as guests filter back into the dining room, chatting over dessert and coffee, Hefner jaunts upstairs with his gals to get dressed for a night of clubbing at the town's hottest spots, as they usually do when "movie time" ends. It's time to leave the fantasies of the silver screen behind for the fantasies he's made come true in real life--at least until next evening's screening, to be shared again with great friends. He remarks, in true wonderment, "As good as my life appears to be from the outside, it is even better."

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