After leaving college, Whitehead wrote for The Village Voice.
While working at the Voice, he began drafting his first novels.

Whitehead has since produced nine book-length works—seven novels and two non-fiction works, including a meditation on life in Manhattan in the style of E.B. White's famous essay Here Is New York.
The books are 1999's The Intuitionist, 2001's John Henry Days, 2003's The Colossus of New York, 2006's Apex Hides the Hurt, 2009's Sag Harbor, 2011's Zone One, a New York Times Bestseller; 2016's The Underground Railroad, which earned a National Book Award for Fiction, and 2019's The Nickel Boys.
Esquire magazine named The Intuitionist the best first novel of the year, and GQ called it one of the "novels of the millennium."
Novelist John Updike, reviewing The Intuitionist in The New Yorker, called Whitehead "ambitious," "scintillating," and "strikingly original," adding, "The young African-American writer to watch may well be a thirty-one-year-old Harvard graduate with the vivid name of Colson Whitehead."

Whitehead's The Intuitionist was nominated as the Common Novel at Rochester Institute of Technology (RIT).
The Common Novel nomination was part of a long-time tradition at the Institute that included authors like Maya Angelou, Andre Dubus III, William Joseph Kennedy, and Anthony Swofford.

Whitehead's non-fiction, essays and reviews have appeared in numerous publications, including The New York Times, The New Yorker, Granta, and Harper's.

His non-fiction account of the 2011 World Series of Poker The Noble Hustle: Poker, Beef Jerky & Death was published by Doubleday in 2014.

He has taught at Princeton University, New York University, the University of Houston, Columbia University, Brooklyn College, Hunter College, Wesleyan University, and been a Writer-in-Residence at Vassar College, the University of Richmond, and the University of Wyoming.

In the spring of 2015, he joined The New York Times Magazine to write a column on language.

His 2016 novel, The Underground Railroad, was a selection of Oprah's Book Club 2.0, and was also chosen by President Barack Obama as one of five books on his summer vacation reading list.
In January 2017 it was awarded the Carnegie Medal for Excellence in Fiction at the American Library Association Mid-Winter conference in Atlanta, GA.
Colson was also honored with the 2017 Hurston/Wright Award for fiction presented by the Zora Neale Hurston/Richard Wright Foundation.
The Underground Railroad won the 2017 Pulitzer Prize for Fiction.
Judges of the prize called the novel "a smart melding of realism and allegory that combines the violence of slavery and the drama of escape in a myth that speaks to contemporary America."

Whitehead's seventh novel, The Nickel Boys, was published in July 2019.
The novel was inspired by the real-life story of the Dozier School for Boys in Florida, where children convicted of minor offences suffered violent abuse.
In conjunction with the publication of The Nickel Boys, Whitehead was featured on the cover of TIME Magazine for the July 8, 2019 edition, alongside the strap-line "America's Storyteller".
The Nickel Boys won the 2020 Pulitzer Prize for Fiction.
Judges of the prize called the novel "a spare and devastating exploration of abuse at a reform school in Jim Crow-era Florida that is ultimately a powerful tale of human perseverance, dignity and redemption."
It is Whitehead's second win, making him the fourth writer in history to have won the prize twice.

Currently, Whitehead is working on an eighth novel (originally conceived and begun before he wrote The Nickel Boys).
The work-in-progress is an untitled crime novel set in Harlem during the 1960s.

In 2020 Whitehead criticized the Internet Archive's National Emergency Library program, launched in response to the COVID-19 pandemic, writing on Twitter: "They scan books illegally and put them online.
It’s not a library."
After leaving college, Whitehead wrote for The Village Voice. While working at the Voice, he began drafting his first novels.
Whitehead has since produced nine book-length works—seven novels and two non-fiction works, including a meditation on life in Manhattan in the style of E.B. White's famous essay Here Is New York. The books are 1999's The Intuitionist, 2001's John Henry Days, 2003's The Colossus of New York, 2006's Apex Hides the Hurt, 2009's Sag Harbor, 2011's Zone One, a New York Times Bestseller; 2016's The Underground Railroad, which earned a National Book Award for Fiction, and 2019's The Nickel Boys.Esquire magazine named The Intuitionist the best first novel of the year, and GQ called it one of the "novels of the millennium." Novelist John Updike, reviewing The Intuitionist in The New Yorker, called Whitehead "ambitious," "scintillating," and "strikingly original," adding, "The young African-American writer to watch may well be a thirty-one-year-old Harvard graduate with the vivid name of Colson Whitehead."
Whitehead's The Intuitionist was nominated as the Common Novel at Rochester Institute of Technology (RIT). The Common Novel nomination was part of a long-time tradition at the Institute that included authors like Maya Angelou, Andre Dubus III, William Joseph Kennedy, and Anthony Swofford.
Whitehead's non-fiction, essays and reviews have appeared in numerous publications, including The New York Times, The New Yorker, Granta, and Harper's.
His non-fiction account of the 2011 World Series of Poker The Noble Hustle: Poker, Beef Jerky & Death was published by Doubleday in 2014.
He has taught at Princeton University, New York University, the University of Houston, Columbia University, Brooklyn College, Hunter College, Wesleyan University, and been a Writer-in-Residence at Vassar College, the University of Richmond, and the University of Wyoming.
In the spring of 2015, he joined The New York Times Magazine to write a column on language.
His 2016 novel, The Underground Railroad, was a selection of Oprah's Book Club 2.0, and was also chosen by President Barack Obama as one of five books on his summer vacation reading list. In January 2017 it was awarded the Carnegie Medal for Excellence in Fiction at the American Library Association Mid-Winter conference in Atlanta, GA. Colson was also honored with the 2017 Hurston/Wright Award for fiction presented by the Zora Neale Hurston/Richard Wright Foundation. The Underground Railroad won the 2017 Pulitzer Prize for Fiction. Judges of the prize called the novel "a smart melding of realism and allegory that combines the violence of slavery and the drama of escape in a myth that speaks to contemporary America."
Whitehead's seventh novel, The Nickel Boys, was published in July 2019. The novel was inspired by the real-life story of the Dozier School for Boys in Florida, where children convicted of minor offences suffered violent abuse. In conjunction with the publication of The Nickel Boys, Whitehead was featured on the cover of TIME Magazine for the July 8, 2019 edition, alongside the strap-line "America's Storyteller". The Nickel Boys won the 2020 Pulitzer Prize for Fiction. Judges of the prize called the novel "a spare and devastating exploration of abuse at a reform school in Jim Crow-era Florida that is ultimately a powerful tale of human perseverance, dignity and redemption." It is Whitehead's second win, making him the fourth writer in history to have won the prize twice.
Currently, Whitehead is working on an eighth novel (originally conceived and begun before he wrote The Nickel Boys). The work-in-progress is an untitled crime novel set in Harlem during the 1960s.
In 2020 Whitehead criticized the Internet Archive's National Emergency Library program, launched in response to the COVID-19 pandemic, writing on Twitter: "They scan books illegally and put them online. It’s not a library."
Colson Whitehead