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Michael Rapaport discussed some intriguing casting what-ifs for the 1995 film "Higher Learning," directed by John Singleton. Rapaport revealed that late rapper Tupac Shakur was originally set to play the role of Malik Williams, a part that ultimately went to Omar Epps. Meanwhile, Leonardo DiCaprio was considered for Remy, a character Rapaport ended up portraying. DiCaprio reportedly declined in favor of a "little film about a boat," jokingly alluding to "Titanic," which catapulted the actor to global fame. Gwyneth Paltrow was also initially slated to join the cast as Taryn, later played by Jennifer Connelly. Discussing the film's development, Rapaport reflected on his respect for director John Singleton and his experience during filming. He also touched on auditioning with Ice Cube, emphasizing his admiration for the rapper and actor. Though casting changed, "Higher Learning" remains a pivotal film exploring racial and social issues, with Rapaport cherishing his collaboration with Singleton and the cast.