A slew of steady stage work followed, and Esposito soon found his niche playing mostly black characters in the critically acclaimed films of Spike Lee, including School Daze (1988), Do the Right Thing (1989), Mo' Better Blues (1990) and Malcolm X (1992).
Other notable feature film credits include supporting roles in Bob Roberts (1992), The Usual Suspects (1995), Ali (2001), Derailed (2005), Last Holiday (2006) and Sherrybaby (2006), in which he plays the title character's parole officer.