In 1989, the writer and filmmaker Trey Ellis published a concise, manifesto-like essay titled “The New Black Aesthetic.” His argument was fairly straightforward and, in retrospect, perhaps its significance was the fact that he had to write it at all. Ellis believed that the coming decade demanded a new, eclectic approach to African-American cultural expression, one that would reckon with the full continuum of the black experience, from the city to the suburbs. The signs were all around us: the knotty, urbane films of Spike Lee; the punkish bravado of Fishbone; all the artsy, middle-class kids exploring identities that weren’t beholden to readymade signifiers like “Africa and jazz.” This would be a generation of “cultural mulattos,” postmodern children of the multicultural age who were comfortable in a variety of settings, a kind of hopeful, flexible, and self-empowered embodiment of W. E. B. DuBois’s “double consciousness.”

If only it were so simple. That Ellis felt compelled to issue such a hopeful yet fundamentally basic call speaks to the sad entanglements of American racial politics at the time, and the ways in which representational spaces for African-Americans continued to winnow. So it was a landmark event when, in 1996, Paul Beatty published “The White Boy Shuffle,” a satirical exploration of racial identity’s seeming elasticity. It tracked the life and times of young Gunnar Kaufman, a “funny, cool, black guy” hailing from a long line of “spineless,” far-from-righteous African-Americans: deserters, cowards, a freedman who wandered back into slavery, a great-great-uncle who painted the “COLORED ONLY” signs ubiquitous during Jim Crow. As a literary archetype, everything about Gunnar feels off, from his beach-bum persona to the way his family runs counter to traditional uplifting narratives of the American Dream: his father works as a sketch artist for the racist L.A.P.D.; his mother moves the family from their affluent, white suburb back to “the ghetto.” In the course of the novel, Gunnar, a sensitive young poet and reluctant basketball player, eventually becomes his generation’s messiah. It does not end well: he inspires a movement of disaffected black youth to martyr themselves.

Phil Jackson, back when he was coaching the Los Angeles Lakers, gave Kobe Bryant a copy of Beatty’s book, ostensibly because Kaufman’s fish-out-of-water upbringing reminded Jackson of Bryant’s childhood in Italy. Bryant would later say that he enjoyed reading it, though he didn’t appreciate Jackson’s assumptions about his life. Maybe he felt like his coach was calling his blackness into question as well. “The White Boy Shuffle” was published at the high point of nineteen-nineties multiculturalism—Gunnar, the ultimate “cultural mulatto,” attends a P.C.-obsessed school called Mestizo Mulatto Mongrel Elementary—and the novel was knowingly inauthentic. Yet despite the whimsical deconstruction of blackness and identity and the self-aware iconoclasm of Beatty’s anti-heroes, the same revelation awaits: America will never allow you to be as free as you dream of being, even if those dreams are personal, small, and involve something as simple as not picking up a basketball.

Earlier this month, Beatty published his superb fourth novel, “The Sellout.” It arrives at, and responds to, a very different political moment. If Beatty’s previous novels skewered the early days of institutional multiculturalism and the weird frictions of integration, then “The Sellout” captures a time when diversity has gone completely mainstream. It’s animated by a desire to understand the paradoxes of that time—of a multitudinous America that contains both Barack Obama’s election and Trayvon Martin’s murder. A time when the conversation on race seems both terminal and never-ending, when the promise of ever more conversation is offered as an end in itself. When Starbucks encourages its customers to talk about race with their local barista. As Beatty forewarned in 1996, “Everything was multicultural, but nothing was multicultural.”

“The Sellout” is set in a fictitious “agrarian ghetto” just outside of Los Angeles called Dickens, a melting pot so troubling to California’s cheerful branding that the powers that be have erased it from the map, stealing away the last stable source of the community’s collective identity. The plot is fairly straightforward. It’s about a protagonist—known around Dickens as BonBon or the Sellout, though his family name is Me—whose father raised him according to the rigid dictates of academic theory. For example, his father lined the seven-month-old BonBon’s bassinet with “toy police cars, cold cans of Pabst Blue Ribbon, Richard Nixon campaign buttons and a copy of The Economist,” firing a gun and shouting racial slurs whenever the boy so much as breathed in the direction of these totems of the white mainstream. Learning the words to “Sweet Home Alabama,” his father forewarned, would not help you fit into the world out there.

When BonBon’s father dies, BonBon temporarily inherits his job as the neighborhood “nigger whisperer,” the ad-hoc mentor who talks young black men off bridges and highway overpasses, and out of their moments of beaten-down desperation. But BonBon soon begins to question the point of selling those around him a bit of hope to get through their otherwise despondent days. He earns the name Sellout when he refuses to abide by the safe political orthodoxies of the Dum Dum Donut Intellectuals, his father’s onetime rivals, a group of myopic local thinkers who gather periodically to figure out schemes for black uplift (sample: “EmpowerPoint, a slide presentation ‘African American software’ package”). The Sellout’s ideas are too “problematic”—“the code word black thinkers use to characterize anything or anybody that makes them feel uncomfortable, impotent and painfully aware that they don’t have the answers to questions and assholes like me.” Those ideas involve restoring Dickens’s place on the map by agitating for a return to slavery and segregation.

Like “The White Boy Shuffle,” “The Sellout” follows the dwindling sunset of American possibility. It’s dark, nihilistic, pessimistic, and impolite, and it makes a mockery of the dream that things will get better—that a new era of racial harmony is right around the corner. “That’s the problem with history,” BonBon thinks, regarding his friend Hominy Jenkins, an old-timer who’s disturbingly comfortable with how Jim Crow warped his outlook. Freedom vexes Hominy; instead, he lives in the past, carrying with him a masochistic desire to constantly be put back in “his place.” “We like to think it’s a book—that we can turn the page and move the fuck on,” BonBon continues. “But history isn’t the paper it’s printed on. It’s memory, and memory is time, emotions and song. History is the things that stay with you.” Eventually, BonBon becomes a part of that history, when he lands in front of the Supreme Court, “the latest in the long line of landmark race-related cases,” from Plessy v. Ferguson to the time they tried to bury 2 Live Crew. Then again, BonBon wonders, what story of uplift do those cases narrate?

No doubt all of this sounds crass and absurd: I’ve just described a book that features an elderly African-American man who begs to be taken as a slave and a younger one who aspires to re-segregate buses and schools. But what leavens “The Sellout” is its humor—the way Beatty lampoons self-important leaders and those naïve enough to believe in them, his ear for how much funnier things get when they’re just a bit off. And then there’s the weight and scandal of the realization, the decaying heart of the matter, when you remember that this is slavery and segregation that Beatty’s joking about. The point, for Beatty, is never to give up and give thanks for being part of America. It’s to cast a sideways glance at the very notion of progress—to embrace what Beatty calls an “unmitigated blackness” that realizes that, “as fucked up and meaningless as it all is, sometimes it’s the nihilism that makes life worth living.”