Reading Your Way Through Colson Whitehead

Arguably the novel that catapulted Whitehead from a respected emerging author into a mainstream lit star, and the basis for the Amazon Prime Video series directed by Barry Jenkins, The Underground Railroad won Whitehead his first Pulitzer. The book follows the harrowing journey of Cora, a young slave on a Georgia plantation, as she escapes via the literal underground railroad, encountering different manifestations of racism and oppression in each state she passes through. Through vivid prose and surreal twists, Whitehead explores the brutal realities of American slavery and the resilience of those who fought against it.

Whitehead’s second Pulitzer-winning book follows Elwood Curtis, a Black boy growing up in the 1960s Jim Crow South who is unfairly sentenced to a juvenile reformatory called the Nickel Academy—a school that is, in fact, a chamber of horrors. Based on Dozier Academy, a real reform school that operated for 111 years and was racially segregated until the 1960s—only closing in 2011—this powerful novel is called “a necessary read” by former President Barack Obama.

Whitehead’s first novel, which was nominated for the PEN/Hemingway award for fiction, explores warring factions of the Department of Elevator Inspectors: the Empiricists, who work by the book, and the Intuitionists, who check elevator safety by question and meditation. At the center is Lila Mae, the first Black female elevator inspector and an intuitionist, who just so happens to have the highest accuracy rate in the entire department. As she navigates through layers of corruption and intrigue, the novel delves into themes of race, technology, and societal power structures.

A finalist for the National Book Critics Circle Award in 2021, Harlem Shuffle is a novel about race, history, power, and Harlem, mixed with the genre of a period-set thriller. Ray Carney is a straight-laced salesman of furniture with a loving wife and second kid on the way. But he’s worked to be straight-laced, and when his cousin Fredie falls in with a crew who plans to rob a high-end hotel, he volunteers Ray to help out.

Nominated for the top prize of mystery writing, the Edgar Award, Crook Manifesto continues a historical exploration of Harlem in the 1970s full of power and glory. The story follows Ray Carney, a man navigating the thin line between his newfound straight-laced ways and a return to his rebel days. Whitehead's nuanced portrayal of this turbulent era, sparked by Carney's pursuit of Jackson 5 tickets, explores themes of power, survival, and the complexities of moral choices. While we suggest reading Harlem Shuffle first, this book can be read as a standalone.

In his second novel, Whitehead intertwines the legend of John Henry, a steel-driving folk hero, with the modern-day story of a journalist named J. Sutter assigned to cover a festival celebrating Henry's legacy. The multi-layered and funny novel, which blends history, adventure, and wry anthropological wit and wisdom, caught the eye of author John Updike and set Whitehead up to receive the Macarthur “Genius” fellowship.

A comedic tour de force, Apex Hides the Hurt takes readers to Winthrop, a town that decides it needs a new name. The resident tech millionaire wants to call it Prospera; the mayor wants to name it in homage to the founding Black settlers; and the upper class don’t want it to change at all. So, they decide to hire a consultant. But a new name may be just the beginning. . .Through sharp wit and keen observation, Whitehead explores the complexities of language, branding, and the ways in which communities grapple with their pasts.

Whitehead grew up spending summers in Sag Harbor, New York, where this autobiographical, adolescent coming-of-age story is set. In fact, like the protagonist, Benji, Whitehead was once involved in a BB gun shooting contest (and he has the scar to prove it!). The episodic novel traces Benji’s summer with friends, almost-summer-loves, and a job slinging ice cream that will fill you with nostalgia and summer longing. Watch out for its potential upcoming series adaptation!

A mix of zombie horror and literary suspense, "Zone One" takes place in the lower half of Manhattan, the part of the island that’d been successfully reclaimed by armed forces after a pandemic has left only the uninfected and the infected—the living, and the living dead. The worst seems to be thankfully over, and Mark is clearing the lower part of the city of feral zombies. With his characteristic wit and incisive social commentary, Whitehead transforms the familiar zombie narrative into an inventive take on human resilience and rebuilding society post-disaster.

In "Colossus of New York," Colson Whitehead offers a kaleidoscopic view of America's most iconic city. Blending third and first-person narratives, this nonfiction work presents a series of vignettes and meditations that capture the essence of New York's diverse landscapes and inhabitants. It’s a great read for on-the-go travel, a pre- or post-NYC trip, or when you just want a getaway within a book.