In his story​ ‘The Student’, Chekhov writes of a young seminarian who comes across two widows warming themselves at a fire:

And now, shrinking from the cold, he thought that just such a wind had blown … in the time of Ivan the Terrible and Peter, and in their time there had been just the same desperate poverty and hunger, the same thatched roofs with holes in them, ignorance, misery, the same desolation around, the same darkness, the same feeling of oppression – all these had existed, did exist, and would exist, and the lapse of a thousand years would make life no better.

At first this insight dismays him, but he comes to accept that the past ‘is linked with the present by an unbroken chain of events’ and that ‘he had just seen both ends of that chain; that when he touched one end the other quivered.’ He is suddenly relieved. It seems there is a permanence to things that both guarantees one’s own tribulations and makes them merely an insignificant part of a larger unalterable order. The story was written in 1894, in the aftermath of serfdom, but it expresses – however ironically – a sentiment prevailing in many of the most influential parts of black America today.

Over the past few years, roughly the entire second term of the Obama administration, a consensus has taken shape online and also in more traditional arenas of American political activism and cultural production. Inspired by the disproportionate impact of the economic collapse of 2008 and by growing awareness of the failure of the policy of mass incarceration as well as scores of high-profile travesties of justice – notably the death of Trayvon Martin and the acquittal of his murderer, George Zimmerman, which gave birth to the #BlackLivesMatter movement – alongside many more ambiguous affronts (such as the lack of nominees of colour at the 2015 Academy Awards, which gave birth to the #OscarsSoWhite campaign), the rapturous, impossibly short-lived post-raciality of the first black presidency has been usurped by a backward-looking social consciousness best expressed by the internet neologism ‘wokeness’. (Chekhov’s student ‘got woke’ that cold night in the Russian countryside.)

In times of strife, there is something seductive, even romantic, about the kind of transhistorical thinking the new social consciousness invokes, articulated most notably in Ta-Nehisi Coates’s bestseller, Between the World and Me. ‘I can’t secure the safety of my son,’ Coates said in his acceptance speech for the National Book Award. ‘I can’t go home and tell him that it’s going to be OK … I just don’t have that right, I just don’t have that power.’ The power he does have, the power anyone who is black can have, he decides, is a negative one: it lies in the refusal to buy into the possibility of progress (‘You won’t enrol me in this lie’). This sentiment, virtually unspeakable eight years ago, now permeates black cultural output, taking in everything from popular music like Kendrick Lamar’s To Pimp a Butterfly and Beyoncé’s Lemonade, as well as her sister Solange’s A Seat at the Table, to films like Steve McQueen’s 12 Years a Slave, Ava Duvernay’s 13th and Nate Parker’s much hyped The Birth of a Nation, to books like Michelle Alexander’s The New Jim Crow, Jesmyn Ward’s anthology The Fire This Time, James McBride’s The Good Lord Bird and the poet Claudia Rankine’s award-winning Citizen. In a recent interview with the Los Angeles Times, on receiving the MacArthur ‘Genius’ grant, Rankine acknowledged as much: ‘To me, the getting of this honour is … the culture saying: “We have an investment in dismantling white dominance in our culture. If you’re trying to do that, we’re going to help you” … The MacArthur is given to my subject through me.’ The moral of the story is clear: if you are a serious black artist working today, whether you like it or not, you’re going to have to wake up.

Before the publication of The Underground Railroad, his sixth novel – a mostly straightforward and historically realistic tale of a slave’s escape from southern bondage into tenuous northern freedom – it would have been difficult to imagine a less obvious candidate for the title of Woke Black Artist of the Year than the 47-year-old Colson Whitehead. He distinguished himself in his late twenties with his first novel, The Intuitionist (1999), an explosively original story set in a fantastical world of elevator inspectors, and quickly won critical acclaim on the strength of a rollicking, hyper-idiosyncratic body of work that refused to adhere to the mandates of identity politics or the constrictions of literary genre. Writing with David Foster Wallace-level verbal firepower, he was prepared to subvert the simplistic clichés attached to blackness – and the impulse towards sentimentality that goes along with them. At the height of black rapture over Obama’s election, Whitehead published an irreverent, almost flippant op-ed in the New York Times entitled ‘Finally, a Thin President’, which made a mockery of the notion that an earth-shattering symbolic power was attached to the historic achievement. The next year, he published another satirical op-ed in the New York Times, this one a guide for blocked novelists in search of fresh material. One of his more eyebrow-raising suggestions was what he called the Southern Novel of Black Misery. ‘Africans in America,’ he wrote,

cut your teeth on this literary staple. Slip on your sepia-tinted goggles and investigate the legacy of slavery that still reverberates to this day, the legacy of Reconstruction that still reverberates to this day, and crackers. Invent nutty transliterations of what you think slaves talked like. But hurry up – the hounds are a-gittin’ closer! Sample titles: ‘I’ll Love You Till the Gravy Runs Out and Then I’m Gonna Lick Out the Skillet’; ‘Sore Bunions on a Dusty Road’.

This op-ed appeared on the heels of his 2009 novel, Sag Harbor, a thoroughly uneventful but frequently brilliant autobiographical account of an upper-middle-class black holiday enclave in the Hamptons. That book, set in the summer of 1985, accomplished what very few people attempt to do with the contemporary black American experience: remove it entirely from the realm of extremes. Sag Harbor isn’t a lament about nightmarish, historically predetermined agony or a celebration of fairytale-worthy, impossible to replicate individual talent and success. It doesn’t deny the persistence of racism or fetishise it: anti-blackness, in Sag Harbor as in real life, is just one facet of black experience, no longer the entirety or perhaps even the majority of it – if it ever was. Told from the perspective of a 15-year-old Whitehead stand-in called Benji, Sag Harbor provides many clues about the author’s own Manhattan-bred, Harvard-educated relationship to the inheritance of racial trauma. Noting the reverence with which his parents’ generation spoke of the pioneering black sociologist W.E.B. Du Bois, who had, according to legend, once attended a fish fry in Sag Harbor, Benji confesses: ‘There were Famous Black People I had never heard of, but it was too late to ask who they were because I was old enough, by some secret measure, that it was a disgrace that I didn’t know who they were, these people who had struggled and suffered for every last comfort I enjoyed.’ The riff continues:

Years later in college I’d read his most famous essay and be blown away. And I quote: ‘It is a peculiar sensation, this double-consciousness, this sense of always looking at one’s self through the eyes of others, of measuring one’s soul by the tape of a world that looks on in amused contempt and pity. One ever feels his two-ness – an American, a Negro; two souls, two thoughts, two unreconciled strivings; two warring ideals in one dark body, whose dogged strength alone keeps it from being torn asunder. The history of the American Negro is the history of this strife – this longing to attain self-conscious manhood, to merge his double self into a better and truer self.’ I thought to myself: ‘The guy who wrote that was chowing fried fish behind my house!’

There are very few black American authors working today who would publish a sentence like that last one, regardless of whether or not they had a privileged background. That Whitehead came, this year, to publish the Southern Novel of Black Misery he had lampooned in the New York Times and transcended in Sag Harbor is rather incredible. That he was immediately received as a prodigal son who had at long last come home – Oprah selected The Underground Railroad for her extremely lucrative book club, and it has been shortlisted for the National Book Award – is less surprising. That the most important and acclaimed American novel of the past year, by one of the most talented, protean and iconoclastic American writers of any ethnic group or socioeconomic background is, in effect, an accomplished concession to the mandates of wokeness is notable in the extreme.

This isn’t to imply that The Underground Railroad is a failure. Quite the opposite – once it hits its stride, it is an enchanting tale. We follow a teenage runaway slave called Cora as she flees her sadistic white owner by means of a literal underground railroad operated by a society of freed/escaped slaves and compassionate whites, which no one suspects of penetrating so far into the South (nor does anyone, for that matter, understand how it could possibly work). Whenever it seems Cora is finally in the clear, a single-minded slavehunter called Ridgeway – accompanied by the personification of black complicity in white supremacy, a chilling free black boy called Homer – sends her scrambling back on the lam. However formulaic it may be, the plot is propulsive, and the book is full of vivid images, learned allusions and astute observations, like this one about a white medical student-cum-bodysnatcher in New England:

The other students uttered the most horrible things about the coloured population of Boston, about their smell, their intellectual deficiencies, their primitive drives. Yet when his classmates put their blades to a coloured cadaver, they did more for the cause of coloured advancement than the most high-minded abolitionist. In death the negro became a human being. Only then was he the white man’s equal.

One of the most destabilising aspects of The Underground Railroad is Whitehead’s decision to use his customary, unperturbed tone. He is unflappable, even when recounting matters of absolute racial terror. The mode is highly effective – much more so than any sentimental register – as a means of emphasising the monstrosity involved in the transformation of men, women and children into ‘breathing capital, profit made flesh’. Here he is describing the intergenerational transfer of power on the cotton-producing Georgia estate Cora has escaped from: ‘That summer young Terrance Randall assumed duties to prepare for the day he and his brother took over the plantation. He bought a bunch of niggers out of the Carolinas. Six of them, Fanti and Mandingo if the broker was to be believed, their bodies and temperament honed for labour by nature.’ The master’s favourite, Blake, ‘was a big oak, a double-ration man who quickly proved a testament to Terrance Randall’s investment acumen. The price they’d get for the offspring of such a stud alone.’ And here he is on Terrance’s father’s funeral: ‘The house niggers acted as pallbearers, which everyone thought scandalous at first but on further consideration took as an indicator of genuine affection, one they had indeed enjoyed with their own slaves, with the mammy whose titties they suckled in more innocent times and the attendant who slipped a hand under soapy water at bath time.’

The mundane nature of the evil in such tossed-off remarks demands attention, whereas there is always the danger that the reader has become inured to yet another elaboration of a back-splitting lashing in front of a drooping willow tree. The matter-of-factness of Whitehead’s prose allows him to have his Southern Novel of Black Misery and stand ironically apart from it too. One can’t avoid the impression that, for Whitehead, the subject matter is always in service of the intellectual and narrative dexterity on the page. It’s all so theoretical and cerebral, the book could come with a disclaimer: no author was harmed in the making of this novel.

However compelling​ The Underground Railroad is, it’s hard not to feel that the black art being made right now that will prove to be most enduring will be a lot more like Sag Harbor – forward-facing, electrifyingly alert to the contradictions and complexities of the present, absorbing and refashioning old truths but declining to give in to them. (This is one reason Barry Jenkins’s new film, Moonlight, is vastly more necessary and successful than yet another exploration of slavery along the lines of The Birth of a Nation.) Whitehead would seem to understand this better than anyone. Between Sag Harbor and The Underground Railroad, he published Zone One, a very funny and even moving zombie novel, which bears more than a passing similarity to the new book (the repeated establishment and subsequent violation of presumed ‘safe spaces’; the hapless protagonist distinguished only by an inexplicable knack for survival) while dealing subtly with issues of race and class – a difficult feat to pull off that he makes seem easy. So why a slave novel now? I can only think of something the Jewish American writer Michael Chabon once said about his own writing:

I felt I could bring it all together, that it would be OK. I could do whatever I wanted to do … and it would be OK even if it verged on crime fiction, even if it verged on magic realism, even if it verged on martial arts fiction, whatever it might be, that I was open to all of that and yet I didn’t have to repudiate or steer away from the naturalistic story about two families living their everyday lives and coping with pregnancy and birth and adultery and business failure and all the issues that might go into making a novel written in the genre of mainstream quote-unquote realistic fiction, that that was another genre for me now and I felt free to mix them all in a sense.

It feels as though Whitehead came to a similar conclusion: he could write about fixing elevators, black prep school kids with summer homes, or the rabid undead haunting a post-apocalyptic landscape, and it would be OK; he could skewer the very idea of a slave novel in the US paper of record and then turn around and compose an enormously successful pastiche of one – and that, too, would be OK. It’s all just material at the end of the day.

It’s difficult to accept that Whitehead really did squeeze himself into the artistic confines of wokeness. I would prefer to believe that the story he has given us operates on at least two levels, the second of which many of his new admirers may not immediately notice. I would like to think that he recognises the patterns we are in thrall to, the ways we have come to rely on concepts such as the legacy of American slavery not as historical fact or even societal debt but as parable, as a teachable moment that can’t be – and never should be – conclusively apprehended. It’s a lesson that gains meaning not in the teaching but in the reteaching. It is here, in the realm of the parable, that most black art right now is being made. This is another reason James Baldwin – now so frequently dulled from his shimmering magnitude into a monochrome sentiment: ‘God gave Noah the rainbow sign; No more water, the fire next time!’ – has emerged as the era’s patron saint. The atheist Coates, Baldwin’s designated heir, updates the formula with climate change, but that is a detail: for him and the others, the only legitimate way out of all-polluting original sin and everlasting wickedness is death on an eschatological scale. And so there can be no talk of progress, only the lesson, the struggle, handed down from one generation to the next as a form of timeless wisdom, an unceasing reminder of an inexorable threat.

Yet Whitehead’s own life and family history – three generations with the beach house in that affluent black enclave in Sag Harbor – would seem to complicate such a dismal picture. This brings us back to Rankine’s assessment: the culture really is invested in interrogating (if not dismantling) centuries of white dominance. This is a good thing. But the question remains whether parables of wokeness are the most effective tools for the task. Can you really extinguish a fire with more flames? Can you ever hope to disrupt a cycle of inequality by insisting ever more adamantly that it has and will always exist? At their best, artists like Whitehead show us another possibility.