Hugh Hefner Was ‘Obsessed’ With Getting Britney Spears To Appear On The Cover Of Playboy

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Hugh Hefner died at the age of 91 on Wednesday, and since then there have been tributes rolling in from friends and even the widow of Hunter S. Thompson revealed an interesting story on the Playboy boss. Today we get some insider insight on what it was like to work for the founder of Playboy and his obsession over Britney Spears.

Heidi Parker worker for Hef from 2003-2006 as Playboy’s West Coast Bureau Chief. She remembers Hugh being one of the most “charming people” she had ever worked for and would call her “darling” and ask if she was “doing fine” regularly. Parker also admits that Hefner was a demanding boss. One of his requests that he demanded was for Britney Spears to appear on the cover of Playboy. Parker brought in stars such as Pink, Jaime Pressly, Jennifer Tilly, Eva Herzigova, and Paris Hilton to the Playboy mansion, but in the end, they weren’t good enough because they weren’t Britney Spears, who Hef was allegedly “obsessed” with.

“Hef was dead set on having Spears on the cover in 2004,” Parker wrote in the Daily Mail. “Actually, he always wanted her on the cover, from the day she turned 18-years-old. He had a crush on her. He even faxed me a typed memo about it. The memo basically read, ‘I want Britney Spears for the cover. Signed, Hef.'”

“I want Britney for the cover. I don’t want anyone else. I want Britney or no one! Get her to do it. It would sell like crazy,’ he ordered Parker. She told Hefner it would take time, and Britney’s manager Larry Rudolph said it was a possibility, but Parker knew it was a slim chance of happening. Instead, she offered another young popular singer, “Pink is interested,” Parker told Hefner. “His cold look turned warm and he smiled. ‘Sounds good darling,’ he said as he touched my arm. ‘But don’t forget Britney!’ He winked at me and walked off.”

Hefner never got his wish of having Britney Spears on the cover of Playboy, but he had a pretty decent run regardless.