Hugh Hefner’s beloved copy of Marilyn Monroe's Playbοy issue expected to fetch $5K at auction

Raechal Shewfelt
·Editor, Yahoo Entertainment

Hugh Hefner was not the only person to fall in love with Marilyn Monroe, but he was the only one who put her on the cover of Playbοy’s first issue.

For $500, he famously purchased nude photos Monroe had posed for when she was desperate for a $50 paycheck back in 1949. She was so uncomfortable about shooting the images, set to appear in a calendar, that she made the photographer promise she wouldn’t be identifiable. (So much for that!) But by the time Hefner launched his magazine in 1953, and selected Monroe for its pages, she had appeared in movies such as Gentlemen Prefer Blondes and Niagara and was well on her way to becoming a superstar. Readers snapped up copies of the magazine, and Playbοy was a hit.

Hefner held on to a copy of that debut issue of Playbοy until he died in September 2017, and it’s one of the dozens of items from Hefner’s personal collection that Julien’s Auctions will offer in an event live in Los Angeles and online at juliensauctions.com on Nov. 30 and Dec. 1. Its estimated value is $3,000 to $5,000 — quite a markup from the 50-cent price tag.

Hugh Hefner at the Playboy Mansion in Los Angeles on Feb. 26, 2009. (Photo: Ann Johansson/Corbis via Getty Images)
Hugh Hefner at the Playboy Mansion in Los Angeles on Feb. 26, 2009. (Photo: Ann Johansson/Corbis via Getty Images)
Marilyn Monroe stars in the first issue of <em>Playboy</em> magazine. (Photo: Julien’s Auctions)
Marilyn Monroe stars in the first issue of Playboy magazine. (Photo: Julien’s Auctions)

Alongside the magazine, Hef’s first-edition copy of The Great Gatsby, along with his silk pajamas, pipe and copy of the script from the Saturday Night Live episode that he hosted on Oct. 15, 1977, will hit the auction block as well.

While the Monroe issue was important to Hefner because of all that it meant to his career, he was also personally a fan of the actress. He’s noted that the two were born in the same year — 1926 — and had connections in common. “She was actually in my brother’s acting class in New York,” Hefner told CNN in February 2011. “But the reality is that I never met her. I talked to her once on the phone, but I never met her. She was gone, sadly, before I came out here [to California].”

Hefner was so fascinated with Monroe that, 30 years after she died at age 36, he bought the plot of land beside her grave at Westwood Village Memorial Park & Mortuary in Los Angeles. “Spending eternity next to Marilyn is too sweet to pass up,” he told the Los Angeles Times in August 2009.

Monroe’s feelings about Hefner were more complicated.

Marilyn Monroe in a photo from “Let’s Make Love,” circa 1960 (Photo: Hulton Archive/Getty Images)
Marilyn Monroe in a photo from “Let’s Make Love,” circa 1960 (Photo: Hulton Archive/Getty Images)

“I never even received a thank-you from all those who made millions off a nude Marilyn photograph. I even had to buy a copy of the magazine to see myself in it,” Monroe told a photographer friend, George Barris, as he reported in his 1995 book Marilyn: Her Life In Her Own Words.

Monroe eventually obtained a copy of the issue autographed by Hefner, which sold for a record-breaking $32,000 at another Julien’s Auctions event earlier this month.

The media attention from Monroe’s Playbοy appearance ended up boosting her profile, despite studio executives’ warnings that it would mean the end of her moviemaking days.

“Of course they were wrong,” Monroe told Barris. “The fans, my public cheered when I admitted it was me, and that calendar and that Playbοy first-issue publicity helped my career.”

While Monroe herself earned zilch for her appearance in Playbοy , the sale of Hefner’s prized issue will go to a good cause. All auction proceeds will benefit the Hugh M. Hefner Foundation, which Hefner founded in 1964 to support organizations advocating for civil rights and liberties.

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