Colson Whitehead

“The moment of recognition between the writer and the reader is most beautiful when I’ve hit upon something for myself—and in doing so have articulated something for other people. What it feels like to walk through Central Park on the first day of spring and feel part of this revitalized city; if I can capture that and find the right words, then other people can be there. If I can evoke my losses with the right combination of words, then I can unlock other people’s moments when they’ve been in the same position.”

-Colson Whitehead, episode 463 of Talk Easy with Sam Fragoso

Novelist Colson Whitehead is one of only a handful of writers to win the Pulitzer Prize for Fiction twice—first for The Underground Railroad in 2017, and again for The Nickel Boys in 2020. He joins us on the heels of his latest novel, Cool Machine, the final installment of his acclaimed Harlem trilogy.

We begin with his decision to close out the world of furniture dealer Ray Carney (3:00), why Whitehead felt compelled to keep returning to 125th and Morningside (7:30), and the artistic influences that shaped him as a teenager (14:15). Then, we walk through the personal scenes chronicled in Sag Harbor (15:15), the horror movies that eventually led to Zone One (17:38), and how his latest protagonist’s story unfolds alongside a New York City perpetually destroying and reinventing itself (21:48).

On the back-half, Whitehead reflects on finding his voice as a young writer (31:30), why he “had no choice” but to write his debut novel, The Intuitionist (38:20), and teaching at Princeton alongside the late Toni Morrison (41:05). To close, we discuss the uncertain future of reading (44:55), the specter of AI (48:35), Zohran Mamdani’s first eight months as mayor (51:50), his love letter and elegy to the city after September 11 (55:00), and why, after more than a dozen books, writing still makes him feel a little more whole (1:03:00).