Hugh Hefner Lindsay Lohan

December 17, 2011 by staff 

Hugh Hefner Lindsay Lohan, Hugh Hefner almost didn’t let Lindsay Lohan pose for the most recent issue of Play boy.

Hef’s Chicago editors originally pitched the idea, but Hugh says he wasn’t convinced it would be a good fit. Sure, Lohan, 25, has all the right star power, but she has been in a tough spot in her life for a little while now, so Hefner was a bit taken aback by the idea.

“It really came as a surprise to me,” Hefner, 85, tells E! News. “I kind of had mixed emotions about it initially, and then it turned into something bigger than life.”

The magazine’s founder admits that it’s because of the Lohan’s difficult few years that he initially doubted whether she should do a spread in Play boy.

“I wasn’t quite sure where she was at in her life, obviously,” he says. “It depends on whether it’s Tuesday or Thursday.”

So what about those reshoots that occurred just before Lohan’s recent five-hour stint in jail? Apparently Hefner wasn’t satisfied with the look of the photos, finding the style unflattering and not as polished as he wanted — so he demanded a second go. Judging by the leaked cover and photos of Lohan, it sounds like he did a pretty good job remedying the situation.

“The pictorial and the concept for the pictorial came from me,” Hef reveals. “She had done semi-n*des before. I wanted to do something that would be memorable. So what is more natural, since she is a huge fan of Marilyn Monroe, than do something that is a tribute to the red-velvet, Tom Kelley photo shot of Marilyn Monroe that was our very first Playmate?”

As for those rumors that Lohan had reservations about just how much skin she was showing in the shoot, Hef says there was a bit of back-and-forth on that subject.

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