Hugh Hefner Had 'Mixed Emotions' About Lindsay Lohan Doing Playboy

By Dahvi Shira

12/19/2011 at 06:30 PM EST

Hugh Hefner believes Lindsay Lohan's Marilyn Monroe-themed Playboy pictorial will be a keepsake – but the media mogul admits he initially had doubts about featuring the embattled actress on its cover.

"The concept came from my editors," Hefner, 85, told PEOPLE during a recent interview at the Playboy Mansion in L.A.

"I had mixed emotions to begin with," he said. "I could not have anticipated, quite frankly, that it would turn out to be such a sensational newsworthy event, or that the pictorial would turn out so well."

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Oddly enough, the two have never crossed paths – even at the photo shoot. Even so, Hefner, who says Lohan, 25, is "carrying around some serious luggage," hopes the Playboy opportunity is a step in the right direction.

"Historically, Playboy pictorials are connected to celebrities at various times in their career," Hefner says. "Sometimes it's the beginning of their career and sometimes it comes at a particular moment – as with Lindsay – that is intended as a turnaround."

Using Drew Barrymore as an example of someone whose career skyrocketed after landing the magazine's cover during a career low, Hefner says his wish is that "this is a born-again beginning for Lindsay. I think there's a rooting interest for her."

Part of the success of the shoot probably stems Hef's direction that Lohan posed fully naked.

During negotiations, "Some of the people around her said, 'No, no, no, I don't want her nude,' " he says. "And I said, 'No, this is how it's going to be. This is how it is.' "

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