Although Gene Wilder and Pryor were never as close as many speculated, the pair starred in four movies together and Pryor helped write the script for Blazing Saddles. Jesse Eisenberg would be an excellent choice to play the comedic actor, as he can bring the same apple-cheeked, melancholy-tinged enthusiasm that made Wilder famous.
Photo by Sebastian Kim. Interview, July 2009.
The problem with casting Richard Pryor is that you have to pick someone as funny as Richard Pryor. This is no mean feat. There is an obvious analogue to Pryor's looping delivery—a comedian that has shown signs that he may soon be ready to step back into the spotlight. Years after famously disappearing from his hit TV show, Dave Chappelle could step into a role that at would allow him to both establish dramatic chops and confront issues close to his own experience. Both comedians went on a life-changing trip to Africa that caused them to abandon previous, more racially risqué material in favor of a less profane but equally socially conscious persona. Chappelle is among the few people who has personally experienced both the high of fame and the levels of introspection that made Pryor such a unique figure. Also, Chappelle is probably the only person on the planet that could be counted on to replicate Pryor's material and maintain its original hilarity.
This is a tough part to cast. Jennifer Pryor (née Lee) first married Pryor in 1981. By 1982, after several alleged incidents of domestic violence, they had divorced. The couple remarried in 2001, and remained together until his death in 2005. Although Jennifer only accounted for two of Pryor's seven marriages, her attachment to the project and marriage at the time of his death suggests that she will play a major role in the film. Winona Ryder both looks like Jennifer Pryor and has extensive experience playing against an insane male lead. Look no further than Heathers or, for a more recent example, her role opposite Michael Shannon in The Iceman. Although the 6' Chappelle would physically dwarf the 5'3" Ryder, she has a mischievous streak that would enable her to stand up to her co-star.
Photo by Michael Haddi. Interview, December 1990.
Jazz legend Miles Davis was also a close friend to Pryor throughout the comedian's life. Davis is most famous for his album Kind of Blue, and for generally being Miles Davis. He was significantly older than Pryor and would have been a mentor to the young performer, although Pryor did not publicly comment on their relationship in the same way that he did about his relationship to Jim Brown. Although Denzel Washington is more traditionally a leading man, he would be an intriguing choice to play the older and wiser Davis. He has extensive biopic experience, and would add a "Hey! That's Denzel Washington!" factor to his scenes. Washington is around the right age and is an undeniable screen presence. He would dominate the scenes with Chappelle in just the right kind of way.
Photo by Herb Ritts. Interview, July 1990.
Jim Brown, the great running back and movie star, played a major role in Pryor's life. According to Pryor, Brown paid a visit to him while he was heavily addicted to drugs (although, to be fair, Pryor claimed in the same standup routine that the accident was caused by the combination of a chocolate chip cookie and skim milk) and the two were close friends. Combining Brown's physicality and presence is a tough challenge. Terry Crews, also a former football player, probably works best as Brown. Pryor claimed that one of Jim Brown's legs was as big as his entire body, and a similar comparison could be made between the massive Crews and the rail-thin Chappelle. Also, IMDb lists "flexing his pectorals" as his trademark, which is always nice to have on-hand.
Jennifer Lee isn't the only woman Pryor married twice. In between his two marriages to Lee, Pryor wed Flynn Belaine, divorced Flynn Belaine, wed Flynn Belaine, and divorced her again. They also had two children together. We think that newcomer Condola Rashad would be excellent as Pryor's fifth and sixth wife.