The 'Mean Girls' actress appears on The Front cover of this month's edition of the raunchy men's magazine but its founder admits he wasn't convinced with the idea at first.
Hugh said: "It really came as a surprise to me. I kind of had mixed emotions about it initially, and then it turned into something bigger than life.
"I wasn't quite sure where she was at in her life, obviously. It depends on whether it's Tuesday or Thursday."
Hugh also revealed how Lindsay, 24, and her family were initially reluctant for her to appear in the spread naked and had to assure them the pictures would be shot in a classy way.
The 85-year-old lothario told E! News: "I think it was essentially mama and the folks around her that kept pushing for less nudity. And I said, 'We're doing a nude pictorial here. We're going to do it in a very classy way and we're going to do it in a way in which it will not be forgotten.'
"I think it was accomplished beyond anything I could have possibly imagined. People will not forget this pictorial."