Originally, writer, producer, and director John Singleton wanted Leonardo DiCaprio to play Remy, while Michael Rapaport was originally going to play Scott Moss. DiCaprio was cast, but unable to be in this movie because of a scheduling conflict with The Quick and the Dead (1995). So Singleton had Rappaport play Remy once Cole Hauser was cast.
Tyra Banks and John Singleton were in a relationship at the time this movie was made.
Tupac Shakur was originally set to play the role of Malik Williams, but he was jailed shortly after getting the part.
Dustin Hoffman was originally considered for the role of Professor Maurice Phipps, who becomes a mentor to Malik Williams. Hoffman wanted the plot to revolve around the professor and the student, but writer, producer, and director John Singleton didn't want that, so Hoffman wasn't cast.
Ironically, most of the Neo-Nazi skinheads were played by Jewish actors.