Hugh Hefner’s After Dark: Speaking Out In America This documentary from Oscar-winning producer/director, Brigitte Berman, explores Hef as a man of his times who also transcended them and features an array of archival footage from his landmark TV shows, Playboy's Penthouse and Playboy After Dark. An Official Selection of the Telluride Film Festival, it also won the Audience Award at the Whistler Film Festival. | Hugh M. Hefner

The late Dick Gregory said he owed a lot to Hugh Hefner, the man who gave the comic his big break. It was also Hef who gave Gregory the funds to help locate the bodies of three slain Civil Rights workers in Mississippi in 1964. Video courtesy of Comedy Central | Hugh M. Hefner