Spike Lee Retrospective: Keep ‘Em Laughing - "Bamboozled" at 25

“New millennium, huh? It’s the same bullshit.”

One could be forgiven if they haven’t heard of, much less seen, Bamboozled. Spike Lee’s largely overlooked foray into the 21st century, which turns twenty-five this year, was anything but a sensation upon its release. It was barely peddled by the studio, derided by the critics, and lost on the audience. Nearly fifteen years into his career, Bamboozled marked the single worst box office gross for a narrative Spike Lee joint. It seemed that nobody, in the year 2000, was open to a satire chock full of low-budget visuals, derogatory language, and blackface; and so, with such a small cultural imprint upon its release, Bamboozled should be a film lost to time. Instead, it’s proven to be timeless. In fact, in many ways, Bamboozled is more relevant today than ever before.

Shot on a handful of camcorders – with a dash of beautiful 16mm – Spike Lee’s first box office bomb is visually a product of its time. Cheap, grainy, real; it’s a film in direct lineage with The Blair Witch Project before it and 28 Days Later after. That visual styling, like it does in those bookending horror hits, lends itself to the quasi-fantastical reality the film is building. But, unlike witches in the woods or corpses in the countryside, Bamboozled’s story isn’t as unrealistic as one might think at face value. 

Two down on their luck performers, a pair of young black men, Manray (Savion Glover) and Womack (Tommy Davidson) have a cheap street gig, tap dancing and begging for change outside a New York City highrise. Inside, Pierre Delacroix (Damon Wayans), a Harvard-educated TV producer isn’t as down on his luck, but he does happen to be the only black man at his network, and he’s tired of being overlooked and undervalued by his white-pretending-to-be-black boss, Dunwitty (Michael Rapaport). To protest his lack of respect – and the network’s overall shunning of black programming – Delacroix and his assistant, Sloan (Jada Pinkett-Smith), take the performers off the street and build a show around them, a pitch destined to fail: Mantan: The New Millennium Minstrel Show.

Spike Lee pulls no punches in this brutal satire (and the tragedy that follows). Mantan, a sketch comedy show, comes equipped with wholly racialized caricatures, a house band dubbed the Alabama Porch Monkeys, and a heavy application of red-lipped, blackface. Mantan is, undeniably, racist. It is also unequivocally successful. Manray and Womack are catapulted into stardom. Despite their reservations, Pierre and Sloan amp up the inflammatory imagery, until personal-professional relationships boil over, taking down the characters and the Minstrel Show with them.

But before the plot takes a turn towards melodrama, Bamboozled operates as a mirror to Mantan: The New Millennium Minstrel Show. Lee, like Delacroix, is pushing the limits of laughter. Like Delacroix, Lee was working as a well-educated black creative in a predominantly white-led, white-oriented entertainment industry. It’s notable, though not particularly insightful to point out, that by the 2000s Spike Lee was aiming to do just what Pierre Delacroix was wishing for: buck the pigeonholing of black artists into stories about “gangsters” and the “projects.” While Bamboozled necessarily wanders back to those areas, it’s really the only time in a decade-plus span where Lee does so. Summer of Sam preceded Bamboozled in 1999, and Lee’s output in the decade that followed tackled 9/11, the politically economic elite, bank heists, Hurricane Katrina, and the Italian front of World War Two. Lee was able to do – with mixed results – what Delacroix wasn’t: break out of the box.

But ironically, where that mirror shatters is in the reception to the Minstrel Show itself. In the script, Mantan is a huge success. In reality, Bamboozled was an unmitigated failure. Where the inner-movie American audience largely embraced the blackface comedy show, real life audiences didn’t. The critics within Bamboozled lionized Mantan. Critics in real life lambasted Bamboozled because of Mantan. The Miami Herald called it an “angry, potentially offensive movie.” The Christian Science Monitor called it an “overstuffed, overambitious jumble.” And Roger Ebert’s main contention was that Spike Lee’s satire had missed the mark. 

“Blackface is so blatant, so wounding, so highly charged, that it obscures any point being made by the person wearing it,” Ebert wrote in his two star review. He argued that Lee’s satire failed the moment his characters donned blackface, because audiences and especially “white people don’t” find blackface funny. A satire out-of-touch with contemporary audiences is bound to fail.

However, as is so often the case with those who eventually earn the title of “genius,” Spike Lee was not wrong. He was just early. 

It turned out that the American audience’s appetite for racialized media that Bamboozled was satirizing was actually dead-on. Almost prophetically so. 

One of the most critically acclaimed and commercially successful television programs of the 2000s was Chappelle’s Show, a sketch comedy show that trafficked, unapologetically, in racist caricatures. (Dave Chappelle, to his credit, ended up walking away from – and thus ending – the show because he felt it had grown too “socially irresponsible.”) Michael Rapaport would end up tanking his career by becoming an out-of-touch racist white guy with money, essentially completing his transformation into the role of Dunwitty. The Roots, the revolutionary hip-hop band helmed by Black Thought and Questlove, were just getting their major breakthrough in 1999 with their album Things Fall Apart when they signed on to portray Mantan’s Alabama Porch Monkeys. Ten years later, they’d replicate their inner-movie success and sign onto a lifetime of sidelining by hitching their wagon to white-bread comedian Jimmy Fallon. Then, of course, there’s Tropic Thunder.

Robert Downey Jr. proved, even if inadvertently, that all of Roger Ebert’s reflections on how far American audiences had flown from the blackfaced sun were wrong. As it turned out, audiences, and especially white people, did still find blackface funny. Moreover, they were able to parse out satirical uses of blackface from “genuine” uses, without losing their laughter. Tropic Thunder grossed over $110 million domestically. Audiences ate it up. As did the critics. (Ebert gave it 3.5 stars.) As did the industry. (Downey was nominated for an Academy Award.) It seemed, suddenly, that America was living inside the world of Bamboozled. 

Of course, that isn’t necessarily true. America had always been living inside the world of Bamboozled. It’s simply that in the year 2000, audiences didn’t want to be told that they were. Nothing had really changed by 2008, when Tropic Thunder was released. The key difference between Bamboozled and Tropic Thunder is that when Robert Downey Jr. wears blackface the joke is on Hollywood – to laugh at Tropic Thunder is to laugh at the absurdity of Hollywood believing we’d laugh at blackface – but, when Savion Glover and Tommy Davidson wear it, the joke is on us. To laugh at Bamboozled is to laugh at either (one) blackface as funny or (two) audiences finding blackface funny. Either way, the joke is on the audience. 

But that’s what makes Bamboozled such a cogent and prescient satire. The joke is on us. Bamboozled went from underseen and derided to “culturally significant,” or at least that’s what was said in 2023, when it was selected to be preserved in the Library of Congress. Audiences can look back on it now, twenty-five years later, and see it as, if not an artifact, a time capsule to a bygone era when audiences “were too dumb” to get it. But, even still, that belies Bamboozled’s central thesis. Bamboozled doesn’t work today because its satire was strictly true in 2000. It works because it’s still true today. 

American audiences might be “more woke” in 2025 than they were in 2000, but the idea that blackface, minstrelsy, and crude caricature as entertainment is bygone would be flatly incorrect. They’ve changed in form, but hardly in spirit. (Digital blackface, for example, is probably more, quantitatively, prevalent today than any form of blackface was in prior decades.) Bamboozled almost certainly would not be getting Congressional preservation and critical retrospectives if it weren’t still relevant today. 

As Pierre Delacroix, drowning under the weight of his creation, stares into his television screen at the end of the film, a montage of American minstrelsy beams back. The Birth of a Nation, watermelon derbies, cartoon monkeys, ‘dance for me,’ Judy Garland’s blackface, Mantan, every racist image imaginable from popular American culture – but still only a sliver of America’s racist iconography – flashes before us. This is where Bamboozled situates itself. This is a subject as old as subjugation. An unending pursuit to chain slavery to showtime. The minstrel show, the American art form that always was. We laughed at it before Bamboozled, and we laughed at it after. But we shamed Spike Lee for asking the forbidden question: “What’s so funny?”