Most of this film was shot only on digital (Mini DV) camcorders, which can be purchased over the counter at any consumer electronics store. While this choice of technology sacrificed quality, it allowed the cinematographers to film with 15 cameras at a time, and it also allowed Spike Lee to get all the footage he needed shot within the film's modest budget. The "Mantan: The New Millennium Minstrel Show" sequences were the only scenes shot using 16mm film.
Alec Baldwin was supposed to appear in the film as himself, but didn't show up on the day of filming. Lee called Matthew Modine to quickly take Baldwin's place.
The names of two characters are based on real performers of the past. "Mantan" came from Mantan Moreland. "Sleep 'n' Eat" was based on Willie Best, who was credited only as "Sleep 'n' Eat" in some early films.
The two award ceremony scenes are parodies of two real award recipients whom Spike Lee has publicly criticized: the first, where DelaCroix is fumbling around and yelling "Show me the money!", is a jab at Cuba Gooding Jr.'s enthusiastic victory speech for winning the Oscar for Best Supporting Actor; the second scene, in which DelaCroix becomes a teary-eyed brown-noser to Matthew Modine, is a shot at Ving Rhames' Golden Globe victory in which he gave teary-eyed kudos to Jack Lemmon.
The "Alabama Porchmonkeys," the house band on "Mantan's New Millennium Minstrel Show," is played by The Roots, a hip-hop band from Philadelphia. The real group would go on to become the house band on The Tonight Show Starring Jimmy Fallon (2014) beginning in 2014.