3. LINDSAY LOHAN

Given that Lohan's father is a meddling, crazy fame whore who just got hit by a bus (nothing serious, it only scrapped the side of his car), she's in desperate need of a good father figure, and Hefner is known to be a great paternal role for his girls. In fact, when Philadelphia Eagles' Hank Basset planned to marry Hef's ex, Kendra Wilkinson, he asked for her hand both from her mother and Hef. Also, dressing as one of Hefner's bunny-clad girlfriends would certainly be a better career choice than her pole-dancing was in I Know Who Killed Me. And her constant arrests are, in general.