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Matthew Sharpe transports the Jamestown settlement into a bleak future.

APOCALYPSE NOW AND THEN Sharpe imagines how America’s bloody past will live on.

APOCALYPSE NOW AND THEN Sharpe imagines how America’s bloody past will live on.

With its war-seared landscapes, survivalist overtones and visions of eco-unfriendly end-times, Matthew Sharpe’s Jamestown reads like an idiosyncratic companion to Children of Men and Cormac McCarthy’s The Road. The novel opens as a vehicle called the Autobus Godspeed cruises out of Manhattan on an expedition to Virginia, the Chrysler Building imploding in the background. This barbed portrait of apocalyptic times comes with a twist. As the Godspeed’s hapless crew—which includes “communications expert” Johnny Rolfe and fisticuffs-prone Jack Smith—heads south, their actions begin to mirror events from America’s distant past. Sharpe’s book may take place in the future, but it’s also, as the title suggests, a retelling of the 17th-century Jamestown settlement. Soon, we’ll meet Pocahontas, a sassy teen living with her father Powhatan’s tribe among long-abandoned office parks.

Asked why he decided to spin events from 400 years ago into a futuristic fantasia, Sharpe, 44, says he wanted to explore how deeply ingrained Jamestown has become in U.S. mythology. “Jamestown is a kind of historical DNA for America,” the author says from his home in Middletown, Connecticut, where he teaches writing and English at Wesleyan (a longtime New Yorker, Sharpe also has an apartment in Manhattan). “I wanted to emphasize that the ways the British settlers acted out upon the natives continue to shape who we are today.”

Sharpe, who cites McCarthy’s ultraviolent Blood Meridian as one of Jamestown’s influences, is particularly interested in the settlement’s rampant brutality. A comic at heart, he lends some of the cruelty a slapstick quality, as if P.G. Wodehouse had been hired to rewrite a Sam Peckinpah script. But the humor never quite dulls the book’s visceral bloodlust. An arrow through the head might conjure up Steve Martin’s “wild and crazy guy” routine, but it’s still an arrow through the head.

“There were times when I would look over what I’d written and think, This is so terrible. Should I go on?” the author says about his book’s unrelenting violence. “And the answer was, Yes, I have to look at it in the face. I want readers to come away with an intimate sense of how bloody our history is.”

As Smith, Rolfe and their bumbling cohorts build a camp on a swampy plot of Powhatan’s territory, Jamestown becomes a vehicle for Sharpe’s live-wire meditations on cross-cultural communication. The author, who says he has “a sort of sweet, Mary Poppins--like hopefulness about the possibilities of American diversity,” peppers the dialogue with allusions to English-language highlights that his destructive characters are on the verge of losing forever; he riffs on King Lear, Martin Luther King Jr. speeches, Emily Dickinson poems and even Velvet Underground lyrics.

In lesser hands, all of this could have congealed into a hard-to-chew postmodern confection, but Sharpe blends morality and the madcap in ways that would make George Saunders’s mouth water. This will be no surprise to fans of the author’s eccentric yet accessible previous work, which includes The Sleeping Father, about a teen whose dad suffers a speech-debilitating stroke, and Nothing Is Terrible, an ode to Jane Eyre narrated by a hermaphrodite orphan.

Jamestown abandons the middle-class milieu of those books, but it still excels at creating extreme characters and imagining how they’ll collide. Sharpe’s portrayal of Pocahontas and Rolfe’s courtship is both sweet and complex. Throughout, the story is bolstered by prose that alternates between droll dialogue and loose-limbed insight. This is how Pocahontas sums up Rolfe’s captain, John Ratcliffe: “He seems to be a walking advertisement for noble ambition encased in an impenetrable shell of bullshit.”

Anyone familiar with the Pocahontas story knows that it ends tragically. In Jamestown, pot-addled reinforcements arrive at the settlement, and Pocahontas returns with Rolfe to Manhattan for her doomed final act. But a subtle optimism brews beneath this tale of inept domination. “When I was 17 I read Joseph Heller’s Catch-22, and it made a profound impression on me about the possibility of understanding politics and war through the prism of comedy,” the author says. With Jamestown, Sharpe nods to that novel in his own inimitable way. He not only continues his mastery of modulating between the melancholic and the absurd, he also transports that potent mix to new, thought-provoking realms.

Jamestown (Soft Skull, $25) is out now.