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A heavyweight champion of the world for three and a half years (November 1986-February 1990), boxer Mike Tyson also earned a historical footnote as the youngest individual ever to win, and lose, the said title in his chosen sport. Both during and after his heavyweight tenure in the ring, Tyson also courted an overwhelming amount of controversy for his reported anti-social behavior, which included raping a beauty pageant contestant in an Indianapolis hotel room (an act for which he received six years in prison, later commuted to three) and biting off a piece of fighter Evander Holyfield's ear, mid-fight (an act that DQ'd him from that particular match and sent the media into a tailspin). For the most part, Tyson spent his early years on-camera in projects exclusively related to boxing, but following his release from prison, he became acquainted with director James Toback (Fingers), and that marked the beginning of a long friendship that witnessed the men frequently working together. Their collaborations commenced with the improvisational, racially themed 1998 drama Black on White (in which Tyson makes an extended cameo and receives a very blatant pass from a gay character played by Robert Downey, Jr.), the erotic drama When Will I Be Loved? (2004), and, ultimately, the documentary portrait Tyson (2008), which Toback put together from over 30 hours of interviews with the then-retired boxer. Aside from the Toback projects, Tyson's résumé also includes small roles in the 2000 boxing comedy Play It to the Bone and the 2006 boxing drama Rocky Balboa.