NEW YORK, NY.- When the oversexed basketball player Latrell Spencer (Terry Crews) turns to his date to sing Vanessa Carlton’s “A Thousand Miles,” he does so to prove his total love of all things white. Spencer is the stereotypical embodiment of the lascivious muscular Black man intent on procuring a white woman to prove his own masculinity. “Once you go Black, you’re gonna need a wheelchair,” he says. And yet, despite the broadness of his carnal desires, his performativity is the comedic soul to director Keenen Ivory Wayans’ astute racial-passing satire “White Chicks.”

A gender-bending film (streaming on Hulu) that wields whiteface to interrogate the appropriation of Black culture into affluent, gendered white spaces, the film, upon initial release, was critically reviled. Roger Ebert named it the seventh worst movie of 2004. “Who was it made for? Who will it play to,” he asked. In the two decades since, however, its spiky critique of white privilege has revealed itself to be far more incisive than its lowbrow humor would indicate.

Best summarized as “Some Like It Hot” meets “The Simple Life,” “White Chicks” follows Kevin Copeland (Shawn Wayans) and Marcus Copeland (Marlon Wayans), two bumbling FBI agents nearing termination. Tasked with protecting two wealthy white women — the shallow Brittany Wilson (Maitland Ward) and her sister, the idiotic Tiffany (Anne Dudek) — from kidnappers, the detectives find trouble when a car crash injures the two women, leaving them unwilling to attend a fashion event in the Hamptons. To save their jobs, Kevin and Marcus pose as the sisters by dressing in skirts and heels, wigs, makeup, prosthetics. And the “white” voices they adopt become their tools.

While blackface has minstrel roots, whiteface arises from a different impulse. Often employed in comedies, the practice enables Black people to pass as white, putting them in proximity to the believed benefits and privileges the skin tone provides. In works like the Whoopi Goldberg corporate satire film “The Associate” or the Eddie Murphy “White Like Me” sketch on “Saturday Night Live,” the practice not only gives the infiltrator a financial and social advantage, it allows the racial passer to upset the perceived stability of racial identity.

In “White Chicks,” the identity switch works in similar fashion with the added twist of a gender swap. When Kevin and Marcus become Brittany and Tiffany, they’re given the privileges of white femininity. In an early scene, set in the Hamptons, a concierge asks for a credit card to hold the room. Kevin and Marcus, stuck with their own debit cards, threaten to throw a “bitch fit” if the hotel doesn’t allow them to check in. After a tantrum, they’re allowed in their rooms.

They also pull the curtain, showing how white people might act when Black people aren’t present: When a song by rapper 50 Cent comes on the car radio, for instance, a trio of white women are aghast when Kevin and Marcus under white makeup use a racial slur in the lyrics. “So? Nobody’s around,” says Kevin. Armed with permission, all of the white women freely shout out the slur.

In her essay “Surviving in Living Color With Some White Chicks,” film scholar Beretta E. Smith-Shomade keenly gives the title of informant to the Wayans brothers, who conceived of the film’s story. Their infiltration of white spaces grant a window to how whiteness operates unseen. In “White Chicks” we hear other white observers derisively call Kevin and Marcus the “Wilt Chamberlain sisters.” We hear one white woman wonder aloud if someone is “Martha Stewart broke or MC Hammer broke.”

In the Wayanses’ roles as informants, however, their greatest weapon is Crews as Spencer. Prototypically in racial-passing narratives, white people are duped while Black people see right through the subterfuge. The extreme artifice of the agents’ garish prosthetics, therefore, is a feature not a bug. While you might expect white people to be fooled by the terrible theatrics, it’s telling that Spencer can’t tell the difference. He unreservedly pursues Marcus as Tiffany, to whom he refers as his white bunny, because she is his ideal woman: She has white skin, but through her breakdancing, her curvier rear and tenacious attitude, has Black attributes.

Spencer’s own insecurities, exemplified through Crews’ incredible mix of slapstick body comedy and sight gags, become a catalyst for unmooring stereotypes about Black masculinity and race. Ultimately, he is pursuing a Black man, destabilizing his own assumptions about what defines manhood and whiteness. By Spencer coveting white femininity, to the point of memorizing “A Thousand Miles” so he might prove his suitability, he also mirrors how people of color, through the media’s representation of race, are programmed to covet whiteness too.

“Oh no, brother; you’ve got to get your own,” Spencer says to a Black man walking close to Marcus/Tiffany. Within that zinger lies a brutal self-erasure of Blackness and a shallow, stereotypical idealization of white femininity that “White Chicks” seeks to lampoon. Moments like that help the film remain a culturally, racially and sexually savvy tale.

This article originally appeared in The New York Times.