Man of the Year (1995)
Man of the Year (1995) is a mockumentary written and directed by and starring Dirk Shafer. The film is a fictionalized account of Shafer's reign as Playgirl magazine's 1992 "Man of the Year" and his struggle with reconciling his public persona as a sex symbol to women with his identity as a gay man. Shafer combines mock interviews (both with some of the actual people involved and with actors standing in for the actual people) with archive footage from Shafer's appearances on talk shows like Donahue, The Maury Povich Show and The Jerry Springer Show (along with an early appearance on Dance Fever) and recreations of events like his Playgirl photoshoots, his "fantasy date" with a Playgirl reader and the death of his friend Pledge Cartwright (played by actor Bill Brochtrup) of an AIDS-related illness to relate the story.
More at Wikipedia.