Who Will Pay $2,000 to Own Hugh Hefner's Silk Pajamas?

Hugh Hefner's Prized Playboy Possessions Up for Auction - 2 Split-H 2018
Dan Tuffs/Getty Images; Courtesy of Julien's Auctions

Fourteen months after the Playboy icon's death, several of his belongings — including a vintage Wurlitzer jukebox ($20,000) and a first edition of 'The Great Gatsby' ($4,000) — will be up for sale, with proceeds set to benefit his civil liberties foundation.

Fourteen months after his death at 91, a load of Hugh Hefner’s possessions is up for sale, with proceeds to benefit his civil liberties foundation. Julien’s will wield the paddle Nov. 30 and Dec.?1., preceded by a Nov. 28 VIP showing at the auction house's headquarters in Beverly Hills, where the icon’s daughter, Christie Hefner, and widow, Crystal, will appear.

Items include Hef’s complete set of bound Playboy editions (estimated to draw up to $40,000), one of his iconic smoking jackets ($5,000), a pair of his silk pajamas ($2,000) and a 1946 coin-operated Wurlitzer jukebox that he programmed with two dozen original 78 rpm albums by the likes of Artie Shaw, Johnny Mercer and Lena Horne ($20,000).

Offerings that showcase Hefner’s collecting impulse (and reveal his inner Rosebud) range from a first edition of The Great Gatsby ($4,000) to a scale model of his childhood home in Chicago ($3,500). “I didn’t even know he had a first edition of The Great Gatsby," says Christie, Playboy Enterprises’ former chair and CEO. "I think you can imagine why he’d be drawn to it, in the sense of the host who threw the most elaborate and fantastic parties, but also just as a great lover of words."

"It’s curious to see gifts you’ve given him yourself become part of the auction," says Christie. "There’s a cool sign I found in an antique store in New Orleans that he’d put up every year at the mansion to kick off the jazz festival, and an old Monopoly board featuring Chicago landmarks, with Playboy being one of them."

One item not up for bidding is Hefner’s holy grail, the 2,600-plus-volume scrapbook collection he personally assembled as a chronicle of his outsize life. "They’ll probably be digitized," says Christie, "and they’ll likely end up with a university."

A version of this story first appeared in the Nov. 28 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.