A docudrama about Playboy founder Hugh Hefner (Randall Batinkoff), as told by longtime assistant Bobbie Arnstein (Natasha Gregson Wagner), who recalls Hef's life, loves and career. Barbi Benton: Rebecca Herbst. Kimberly Conrad-Hefner: Rebecca Romijn-Stamos. Millie: Sarah Trigger. Karen: Angela Little. Vic Lownes: Paul Satterfield.