- Anvilicious: Spike Lee isn't exactly known for subtlety, Bamboozled may be his biggest assault on discretion yet. In the opening scene the film explains what satire is (because it is a satire, get it??) and doesn't go uphill from there.
- Ending Fatigue: By the final act, the film has descended into bizarre melodrama and rambling repetition of its scattershot messages.
- Harsher in Hindsight:
- The film depicts what happens when blackface is brought into the modern age. Eight years later, Saturday Night Live managed to cast the not-at-all-black (but still mixed-race) Fred Arimsen as Barack Obama (until season 38, when they hired Jay Pharoah [a skinny, black guy] to play Obama, as Armisen was about to leave the show and they needed a replacement).
- In 2012, Billy Crystal appeared in blackface at the Academy Awards.
- The film can also be seen as a precursor to a spat between Spike Lee and Tyler Perry in which the former accused the latter of producing Modern Minstrelsy.
- Hilarious in Hindsight: The Roots appear as Mantan's house band. The producer must have recommended them to Jimmy Fallon.
- He Really Can Act: Savion Glover not only gets to show off his legendary tapping abilities, but gives a thoroughly convincing performance as the angry, self-absorbed Manray.
- Some Anvils Need to Be Dropped: While shows have not gone to the outlandish example shown in the movie, shows like Housewives of Atlanta and even the entire network BET have been accused of everything Lee was making a commentary on. Dave Chappelle even infamously abandoned his show after having a crisis of conscience over this.