The African American art star Kehinde Wiley is probably most famous for his official portrait of Barack Obama, tieless and relaxed yet deeply pensive in his chair. Emerald foliage floats around him, entwining his ankles and bursting into jewel-bright blossoms that symbolise his Kenyan and Hawaiian heritage. The 44th president is himself – photoreal to the last nuance – and yet inserted into this wildly decorative thicket. This is the classic Wiley fantasia.

He generally paints less powerful black people than Obama, however: men (and occasionally women) he meets on the streets of the US or Senegal, where he has studios, or in London, where he found models for this latest show. Wiley elevates these people, mainly slotting them into renowned masterpieces – Holbein’s The Ambassadors, say, or Ingres’s equestrian portrait of Napoleon, the horse now ridden by a New Yorker in Timberland boots. He plays beauty against politics, via art history – the overt objective both visual and political dissonance.

At the National Gallery, Wiley has introduced a Senegalese youth in a long overcoat into a pastiche of a Caspar David Friedrich painting – a solitary figure looking out across stupendous mist-furled peaks in a scene of Romantic yearning. But the contemporary wanderer is monumental compared to Friedrich’s modest figure, so the impact of his race is greater – though so is the painting itself, almost four metres high. Past art is enlarged, here, to make you think harder about who has the ownership of landscape, history and art.

There is a blue glow in the folds of the overcoat that speaks of the studio lighting when the original photograph was taken. That Wiley’s paintings are worked up from digital shots is never in doubt. Two men in Nike trainers play pat-a-cake in the centre of another Friedrich reprise – his famous Chalk Cliffs on Rügen – one of them turning to look us straight in the eye, bringing the old image directly into the present. Two more are perilously adrift on icy green seas, one rowing hard, the other on the lookout for land or rescue: desperate refugees, their foreheads nonetheless glinting in the arc lights.

This painting is based on Winslow Homer’s cherished American classic The Herring Net. Indeed, not a single work here relates directly to works in the National Gallery. Wiley’s Ship of Fools II riffs off the eponymous Bosch painting, via Géricault’s Raft of the Medusa (both in the Louvre). It presents four black figures marooned on a boat (its mast the tree from Bosch), waving and shouting and screaming for help. Two more, supposedly in the sea, are clearly standing on some studio floor. Yet the sheer artificiality of the scene is the visual equivalent of Brechtian alienation. You cannot think of these desperate people as sealed off in the hermetic spectacle of a European masterpiece. The old illusions are breached.

Nike ticks, Evian bottles, Timberlands – brands matter to Wiley, along with fashion, makeup, complicated cornrows and dreads. These are global signs of the times, a lingua franca that links the terrible news of black kids dying on the crossing between Haiti and Florida to the drowning of migrants in the Channel. Each T-shirt, knock-off watch and logo is meticulously reproduced to a purpose, though by whose hands is not exactly clear. Wiley employs artists in Beijing, as well as Africa and America, to paint these enormous messages.

The facture is impressive, but the compositions are sometimes awry. Just as Obama doesn’t quite sit within his seat, so these boats don’t sail on actual seas and their occupants never get wet. Photorealism has its risks, as a style, when it meets the rhetoric of 19th-century art, from Friedrich to Homer to the painters of the American sublime, whose ecstatic colours creep into this show. There are fallouts and gaps, here and there, that expose the inadequacies of Photoshop.

Which may be one reason why Wiley’s six-screen film installation, Prelude, is by some way the masterwork of this show. It misses out the middlemen – literally, the old (and new) painters. Wiley flew a group of black Londoners to the frozen wastes of Norway in winter. His camera shows them standing, awed, before glacial fjords and mountains disappearing inside icy fogs. An older man picks his way through deep snow, dapper in his vintage coat. Two youths catch snowflakes on their eyelashes, faces framed in white hoods against the ambient white-out. Two women play pat-a-cake, bravely laughing against the freezing snow.

The sonorous exhortations of Ralph Waldo Emerson to learn to live alone in nature are recited on the soundtrack, which also features a rousing orchestral score by the cellist and composer Niles Luther. Some of the scenes are as succinct as haiku – just a footstep or a smiling face; others follow the protagonists on their perilous journeys; still others are sweepingly panoramic. But all centre on black figures in a white wilderness, which Wiley sees as a kind of cage, and the poignant revelation of people who have never seen, or been seen in, such an inhospitable landscape before, eyes streaming in the biting cold.