Inspired by classic satires of the American entertainment industry—such as Mel Brooks’s The Producers, Sidney Lumet’s Network, and Elia Kazan’s A Face in the Crowd (to whose screenwriter, Budd Schulberg, Bamboozled is dedicated)—Lee’s film is set in a recognizable reality ruptured by outrageous events and centered on strange, larger-than-life characters whose shortcomings ultimately serve to illuminate human frailties. Bamboozled hinges on the frustrated Delacroix’s fateful plan to create a show so outrageously offensive that it will get him fired from Manhattan’s (fictional yet plausible) CNS television network, secure him a healthy severance package, and publicly expose his jive-turkey Caucasian boss Dunwitty (Michael Rapaport, hilariously unpleasant) as a racist clown. Alas, in a twist yanked straight from The Producers, Delacroix’s gamble, The New Millennium Minstrel Show, becomes a runaway hit. This foulmouthed modern spin on traditional minstrel revues features two performers hired for cheap by the vulturous Delacroix: Manray (Savion Glover) and Womack (Tommy Davidson), who are swiftly renamed Mantan (a reference to the controversial 1930s and ’40s black comic actor Mantan Moreland) and Sleep’n Eat. The pair perform comedy and dance routines while encased in blackface makeup and fire-truck-red lipstick, a spectacle that proves to be catnip for an American public insensate to, or perhaps comforted by, its retrograde qualities. The show’s popular and financial success, which Delacroix comes to enjoy, precipitates its creator’s psychological decline, and ultimately leads to many deaths by gunfire.

Yet before the film reaches its inevitable conclusion, Lee delivers some of the best comic filmmaking of his career, not least the bleakly hilarious sequence in which Delacroix, alongside his assistant, Sloan (Jada Pinkett Smith), auditions a motley collection of acts for supporting parts on the show. Delacroix is keen on the loquacious orator Honeycutt (the wiry, superbly unsettling Lee stalwart Thomas Jefferson Byrd), who offers a pungent spin on a Shakespeare standard—“To be or not to be: that’s the muh’fuckin’ question!”—and secures himself a gig as The New Millennium Minstrel Show’s emcee. He is less impressed by a shirtless didgeridoo player (Tony Arnaud), an obese soul singer (Tuffy Questell) who hollers a disgustingly sexist number (“I be smackin’ my hos!”), and the Mau Maus, a rambunctious political rap act–cum–violent rabble, spearheaded by Sloan’s brother Julius (Mos Def), who insists on being referred to as Big Blak Afrika, much to his upwardly mobile sibling’s chagrin. For the role of the house band, the Alabama Porch Monkeys, Delacroix hires a tight funk/hip-hop outfit, played, in a spectacular dash of meta-irony, by members of the real-life socially conscious hip-hop act the Roots.

As the film progresses, the laughs run dry, replaced by a chokingly oppressive pileup of racist imagery, personal tensions, and deliberately operatic plotting. Lee brusquely yet touchingly presents the disjunction between Delacroix and his mother, Orchid (Susan Batson), who is ashamed of him, and his hard-drinking father, Junebug (the great black comic Paul Mooney), a comedian who, pointedly, has retained his dignity by performing culturally specific black material for black audiences in small clubs. A short-lived romance between Manray and Sloan sours when the latter is forced to reveal an earlier dalliance with Delacroix. Though occupying only a few scenes, these romantic pyrotechnics pack a punch thanks largely to Pinkett Smith’s measured, steely incarnation of Sloan. Delacroix eventually meets his maker when she, distraught at the sudden dual losses of her lover Manray (killed by the Mau Maus) and her brother Julius (killed by the New York Police Department), shoots him in the gut. “All I could think of was something the great Negro James Baldwin had written,” blares Delacroix in voice-over as he bleeds to death, “‘People pay for what they do, and still more so for what they have allowed themselves to become, and they pay for it very simply by the lives they lead.’” Delacroix’s thunderbolt of self-knowledge at the exact moment of his expiration is both the film’s cruelest joke and the purest articulation of Lee’s astringent perspective on the nature of choice and consequence for black performers. The film’s only hero is Womack, who quietly walked away from the lucrative but degrading minstrel show before the chaos really hit.

Despite Bamboozled’s bracing qualities and stark emotional force, it was not a huge success on its initial release, grossing a paltry $2.5 million against an already slim budget of $10 million. Perhaps one cannot really blame pleasure-seeking audiences for failing to make a Friday-night beeline to a film that insists, at times with the subtlety of a barbell to the temple—see the hysterically on-the-nose “Timmi Hillnigger” spoof fashion commercial—that American racism is alive and thriving, and that while the arc of the moral universe is long, it bends toward spiritual abjection and comprehensive mental collapse. And though the film received moderately positive notices from some reviewers, it also inspired serious rancor from prominent and predominantly white male voices who opined that it was unnecessary in our enlightened age. Despite Lee’s established track record with probing, confrontational, and controversial explorations of race and identity, it seemed like he’d crossed an invisible line here. “Enough has changed for audiences to know that blackface is ugly and unfunny,” harrumphed the New Yorker’s Anthony Lane, while Roger Ebert, arguably the most influential early supporter of Do the Right Thing, fretted, “Many viewers will leave the theater thinking Lee has misused them.” Slate’s David Edelstein observed that “that chip on [Lee’s] shoulder is fast becoming a tumor,” and Andrew Sarris, writing in the New York Observer, lambasted Lee for his decision to “shock Whitey one last time by rubbing his nose in the blackface obscenities of the past.”

Bamboozled’s near film maudit status made it a tantalizing prospect for me to tackle when a small independent publisher began soliciting pitches for single-film monographs in early 2014. After all, I, too, had initially taken the easy way out, dismissing it as messy and unfocused when I first saw it in London in 2001, as a fifteen-year-old burgeoning cinephile, unprepared to process its stygian provocations. But numerous aspects of the film lingered in my mind, from its acrid scenes depicting casual racism in supposedly progressive workplaces, to some of its least palatable imagery. Once seen, it is impossible to forget the giant, caricatured, mechanical, red-lipped mouth from which Manray and Womack emerge in character onstage, or the intimate, desolate backstage sequences in which the two performers painstakingly apply blackface makeup and red lipstick while gazing at themselves in the mirror, eyes pooling with tears, souls adrift in sorrow.

The film’s unusual aesthetic qualities endured for me as well. Lee’s interest in formal experimentation—traceable from the sudden, gorgeous shift from monochrome to color in She’s Gotta Have It through the bizarre aspect-ratio change in Crooklyn (1994)—ramps up here to a whole new level, evidence of a restlessly ambitious filmmaker increasingly allergic to the idea of a comfort zone. His work with his collaborators is inspired: Sam Pollard’s sinister, ghost-in-the-machine editing patterns foster destabilizing antirhythms within scenes, while the film’s woozily immediate digital cinematography, courtesy of Ellen Kuras, adds a memorably oppressive patina of murk. This rough-hewn look is further complemented by Lee and Kuras’s choice to set up multiple cameras within scenes in order to capture the actors off guard, producing a jittery, unpredictable feel.

As the years passed, the film’s prescience, inextricably linked to its stubborn resistance to comforting narratives of progress regarding race and the media, also became increasingly difficult to ignore. On July 17, 2014, a week after I moved to America from my hometown of London, a father of six, Eric Garner, was killed in Staten Island by an illegal choke hold perpetrated by police officer Daniel Pantaleo. Three weeks later, on August 9, eighteen-year-old Michael Brown was shot to death in Ferguson, Missouri, by police officer Darren Wilson. Brown’s prone body was left in the summer sun for four hours. These shocking incidents, in the wake of other outrages like the 2012 Florida murder of the seventeen-year-old Trayvon Martin by racist vigilante George Zimmerman, inspired waves of activism and resistance but also drew sharp attention to the frequently pernicious way that images of blackness are constructed in the media—the subject that is Bamboozled’s lifeblood. In death, Martin, Garner, and Brown, all black and unarmed, were hurriedly recast as thugs, brutes, and layabouts by a powerful right-wing media tapping into a rich seam of antiblack stereotypes forged in the crucible of American popular art.

Much of this shameful history is conveyed with harrowing microcosmic grace in the three-minute montage that closes Bamboozled. Moments after Lee has depicted the NYPD using excessive force in executing all the Mau Maus (save, pointedly, for their sole white member), he delivers a stately compendium of genuine footage of American film entertainment’s most racially offensive imagery, including blacked-up Hollywood stars like Judy Garland and Mickey Rooney; racist cartoons; black performers like Hattie McDaniel, Stepin Fetchit, and the aforementioned Mantan Moreland in demeaning “coon” and “mammy” roles; and disturbing scenes from films such as Gone with the Wind and D. W. Griffith’s racist, pro-Confederacy epic The Birth of a Nation. The montage would be plenty powerful viewed in isolation, but its poignancy is amplified by Terence Blanchard’s simple, melancholic score, and its affectless presentation in the wake of a narrative marked by excess, incoherence, and choleric rage. It is no stretch to draw a direct connection from the black “savages” (white actors in blackface) marauding through the landscape of The Birth of a Nation to the account provided by Wilson of his fateful altercation with Michael Brown. “It looks like a demon, that’s how angry he looked,” Wilson said of Brown.