The Irony and the Ecstasy of Colson Whitehead

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Colson Whitehead’s ascent in the literary world has seemed, like much of what he does, impressively effortless. Though he’s best known for “The Underground Railroad” and “The Nickel Boys”—both of which were awarded Pulitzer Prizes—his œuvre also includes a mystery set amid rival schools of elevator inspectors, a zombie novel, and an autobiographical coming-of-age story. On this episode of Critics at Large, Vinson Cunningham, Naomi Fry, and Alexandra Schwartz survey Whitehead’s wide-ranging body of work. The hosts are joined by their fellow staff writer Julian Lucas, who recently profiled Whitehead for The New Yorker. Together, they discuss three central works: “The Underground Railroad,” which catapulted its author from literary darling to mainstream celebrity; “Sag Harbor,” which fictionalizes, barely, Whitehead’s summers in the Hamptons and the family dramas that played out there; and “Harlem Shuffle,” the first installment of the crime trilogy that concluded this month, with the publication of “Cool Machine.” On the page, Whitehead is a true Gen X ironist, transmitting heavy histories and themes with levity. Despite the occasional darkness of his subject matter, he’s also one of our funniest novelists. “He has this way of, almost like a standup comedian, drawing you into this playful patter,” Lucas says. “Then your defenses go down, and that’s when he hits you with something that grabs you emotionally, or that pulls you into a story.” Read, watch, and listen with the critics: “The Elusive Promise of the First Person” (The New Yorker) “The Nickel Boys,” by Colson Whitehead “Colson Whitehead’s Big Score,” by Julian Lucas (The New Yorker) “The Colossus of New York,” by Colson Whitehead “The Underground Railroad,” by Colson Whitehead “Sag Harbor,” by Colson Whitehead “Harlem Shuffle,” by Colson Whitehead “Cool Machine,” by Colson Whitehead “Why Bother?” by Jonathan Franzen (Harper’s) “The Odyssey” (2026) “Who Owns the Odyssey?” (The New Yorker) “Don’t Use A.I. to Do This,” by Colson Whitehead (The New York Times)