Kim Kardashian revealed that she later 'regretted' posing for Playboy 2007, despite previously describing it as an 'honour'.
The reality star doesn't look back on the infamous shoot - best remembered for birthing the iconic 'You're doing amazing, sweetie' meme - fondly these days.
Fans of Keeping Up With Kardashians will recall how Kardashian, 44, was seen sitting down with magazine mogul Hugh Hefner, 91, to discuss the requirements in one of the first ever episodes of the show.
Then aged 27, the now mother-of-four was seen visiting the Playboy Mansion with her momager Kris Jenner, 69, to iron out the details of the photoshoot.
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Hefner told Kardashian: "I'm very excited about having you in the December issue. The great face, the hair, the booty. I think it will all look very well."
When Jenner asked how much skin her daughter would have to show, he responded: "It's part of it - but discreetly, in very good taste. That's what sets Playboy apart from other magazines, it's always classy."
Hefner's powers of persuasion ultimately worked, as Kardashian agreed to the shoot and ended up posing for Playboy while wearing nothing but strategically draped pearls and black heels.
"The shots are amazing and I'm so glad I did it," she said on Keeping Up With Kardashians at the time.
However, the socialite ended up living to regret being talked into taking her clothes off for the risqué shoot.
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The accompanying text which came with the 'Crazy for Kim' photoshoot described her as the life of the party 'with grace and aplomb'.
"Kim sets the standard for a new type of sawy star power," Playboy wrote. "She may not have a movie, an album or a line of products to hype, but that doesn't stop her from flaunting everything she's got: bubbly charm, exotic good looks (she's of Armenian descent) and sex appeal that keeps the paparazzi flashing till dawn."
In wake of Hefner's 2017 death, Kardashian shared a post on social media which included behind-the-scenes snaps from the 2007 photoshoot while paying tribute to the controversial editor.
The Skims mogul said in an Instagram story, as per People: "Reminiscing about my Playboy shoots, the amazing parties at the mansion and how much I love Hef! I am honoured to have been part of the Playboy team!
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"Hef, you are legendary and will be greatly missed. I love you!"
But Kardashian has flip-flopped between her feelings towards the shoot in recent years.
At the Keeping Up With Kardashians reunion show to mark the end of the programme after it's 14-year run in 2021, her famous family played a game of 'regret or relive'.
Each person was asked whether they'd like to recreate certain experiences in their life or whether they'd prefer to forget them.
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When the topic of Kardashian's Playboy gig came up, she was seen closing her eyes and scrunching her nose, seemingly grimacing at the memory.
Her relatives chimed in saying, 'Regret, regret,' before she added: "Regret. I’m over it."
Kardashian also explained she felt 'uncomfortable' during the photoshoot in a 2010 interview with Harper's Bazaar.
"I’m sorry I did Playboy," Kardashian said. "I was uncomfortable. [My mum said], 'Go for it, they might never ask you again. Our show isn’t on the air yet, no one knows who you are.
"'Do it and you’ll have these beautiful pictures to look at when you’re my age'."
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I guess sometimes mother's don't know best.
Topics: Kim Kardashian, Hugh Hefner, Playboy, Celebrity
Olivia Burke