Kobi Libiis debut feature The American Society of Magical Negroes starts on a promising note. Aren, a spindly and awkward artist (an endearing Justice Smith) loiters near a yarn sculpture in a gallery. He seems lost in the sea of roving patrons and bustling waiters. It takes a second for us to realize that Aren created the meditative wool work and is struggling to sell it to the mostly white collectors attending this group show. They find the abstract piece illegible; they repeatedly ask about the material (Is it yarn?) while maintaining a distance. These brief encounters are a clever jab by Libii at a visual art world historically enamored of Black figurative artists. Minor drama ensues after Aren is mistaken for a server by a patron and unceremoniously fired by his gallerist. Before he can think straight, the dejected artist finds himself touring the gothic halls of The American Society of Magical Negroes, an organization tasked with maintaining peace by monitoring levels of white discomfort across the country. Their name refers to the trope of Black characters in film and literature who exist only to help white protagonists self-actualize. Roger (David Alan Grier), a no-nonsense wizard, is convinced of Arens talent: With no training at all, the sculptor demonstrates a remarkable ability to capitulate to the needs of white people at the expense of his own. Why not put that to good use?

With this setup, The American Society of Magical Negroes positions itself to skewer magical negroes and lampoon liberal sentimentalism about interracial bonds. But instead of delivering on that potential acidity, the film offers mostly benign observations that might have landed more forcefully a decade ago. Arens first assignment as an official Magical Negro requires him to manage the emotional life of Jason (Drew Tarver), an entitled white male designer at a tech startup. Libii, who also wrote the screenplay, uses their friendship to explore the toll of Arens chronic self-effacement, and weaves in a romance between the reluctant young wizard and his co-worker, Lizzie (An-Li Bogan).

That The American Society of Magical Negroes falls short of expectations is not surprising. The film is part of a recent trend of lukewarm Black satires stuck responding to Obama-era post-racial delusions instead of grappling with the shattered reality were living in. These works follow a boon in the Black satire subgenre robust years that gave us films like Jordan Peeles Get Out and Boots Rileys Sorry to Bother You, as well as television shows like Donald Glovers Atlanta. Those projects excelled in part because they dismantled the self-serving myth of a country redeeming itself from its racist past simply by electing a Black president.

Now that its consensus that the Obama presidency didnt cure Americas race-related ills, what can racial satires tackle? How can they be relevant to the current national moment? Like American Fiction, another well-intentioned project that recently nabbed an Oscar for best adapted screenplay, The American Society of Magical Negroes fails to answer that question, struggling to fulfill the political possibilities of satire. It doesnt implicate audiences for their complicity or, as John Milton once wrote of the genre, strike high, and adventure dangerously.

Long before Get Out brought the racial satire into a more mainstream, Oscar-winning space, there were other films that pointed the way, twisting the subgenre in bold fashion and pushing beyond funny-enough jokes to unleash damning revelations. Spike Lees Bamboozled (2000), Ivan Dixons adaptation of Sam Greenlees 1969 novel The Spook Who Sat by the Door (1973) and Melvin Van Peebles absurdist comedy Watermelon Man (1970) delivered tart but clear-eyed observations about race, the effects of capitalism in the cultural sphere and the influence of white supremacy on interpersonal relationships. They targeted everyone, even the directors themselves.

Bamboozled seethes with Lees frustrations; its humor is so caustic that one ultimately ends up laughing at it in the same way one might laugh at a fatal clown car pileup: very quietly if at all with a fixed rictus born of guilt and gut-level terror, writes Ashley Clark in his book Facing Blackness: Media and Minstrelsy in Spike Lees Bamboozled. The film chronicles the devastating fate of an African American television writer, Pierre Delacroix (Damon Wayans), who creates a minstrel show to save a failing network. Its a more acerbic take on Hollywood than Robert Townsends Hollywood Shuffle which is a kind of precursor to American Fiction and a top-tier example of adventuring dangerously.

Not only do Bamboozleds gritty aesthetic and maniacal spirit bolster its message about Hollywoods racist core, but Lee implicates everyone from the white television executive (Michael Rapaport) to the mixed-race audiences who make Pierres show a success. In the filmmakers vision, the real minstrel show is the American entertainment industry itself. With its scorching commentary about fashion (most notably, a spoof commercial of Tommy Hilfiger), police violence, and classism within the Black community, Bamboozled achieves the discomfort of a successful satire the kind whose message stays with you long after youve stopped laughing.

The Spook Who Sat by the Door is less brash than Bamboozled, but no less brave. Like The American Society of Magical Negroes, the film is concerned with the specter of racist violence. But while Aren joins an organization trying to prevent it, Dan Freeman (Lawrence Cook) infiltrates the CIA to foment conflict. Spook follows Dan as he acts like an Uncle Tom to become the first Black agent in the institution, which has recently come under political pressure to integrate. After Dan resigns from the agency, the film shifts from satire to political thriller. The ex-agent returns to Chicago as a social worker and trains young Black men to become freedom fighters. The sendup of bureaucratic operations at Langley is merely a cover for a galvanizing story of Black power.

That Spook and Bamboozled faced extreme criticism and in the case of Dixons film, near erasure speaks to the militant veracity of these satires. Van Peebles Watermelon Man was a studio affair, but it still managed to shock. In this Kafka-esque story (written by Herman Raucher), a white bigot becomes a Black man overnight. The dramatic change could have been played as a sentimental take on how self-proclaimed liberals can still harbor racist views, but Van Peebles, in casting Godfrey Cambridge to play Jeff Gerber as both a Black man and a white man, uses the story to subvert Hollywoods comfort with blackface. Choices like that elevate Watermelon Man from feel-good satire into edgier territory.

The American Society of Magical Negroes lacks that kind of nerve, losing its satirical teeth the harder Aren falls for Lizzie. The courtship subsumes the narrative, which abandons the kind of sharp humor that might have come from fleshing out the Magical Negro organization and investigating how being biracial impacts Arens relationship to whiteness (theres one throwaway joke thats never revisited).

Unlike Libiis film, recent series like Swarm and Boots Rileys Im a Virgo (both on Amazon) model a present and future for racial satires grounded in a political reality that often seems stranger than fiction. Starring an excellent Jharrel Jerome as Cootie, a 13-foot Black boy living in Oakland, Rileys show is a coming-of-age narrative that plays with the same hyper-absurdity and silliness that Riley introduced in Sorry to Bother You. But the series takes distinctive risks, depicting a reality in which everything and everyone has become a commodity, and pushing strong, complex theses about late-stage capitalism, cultural propaganda, political education and what it means to build a peoples movement.

Im a Virgos satire is steeped in an interest in racial capitalism the notion that racism and capitalism are intertwined forces, and you cant combat one without tackling the other. But the satirical elements come couched in a surprisingly warm story of a sheltered boy who defies his parents to discover the world for himself. Along the way, Cootie meets a group of self-described weirdos who become his chosen family and boost his sense of self. The abrasiveness of Rileys vision of America and the tenderness of the coming-of-age story offset and enhance each other. By comparison, The American Society of Magical Negroes and American Fiction (which struggles to make its 2001 source material feel of-the-moment) are timid, their satirical and emotional currents never coalescing, or sparking each other, in a satisfying way.

One of Im a Virgos most poignant storylines involves a key character who dies after being denied care at a local hospital because he lacked proper insurance. The inherent ridiculousness of the shows premise is indeed effective subterfuge for its most urgent message about capitalism as a slow march toward death. In an America where the headlines climate change, artificial intelligence, genocide, fascism and more inspire, to quote Clark again, gut-level terror, the key to making a good racial satire is embracing the absurdity, and the humanity, while keeping the commentary serrated.