Books So Good They Won Multiple Awards

Winning a major literary award is a tremendous achievement. Winning multiple different awards for the same book? That's extraordinarily rare.

Out of the 255+ award-winning books in our database spanning 40+ prestigious literary prizes from 2005-2025, only two books have accomplished this remarkable feat: winning both the National Book Award and the Pulitzer Prize for Fiction.

Let's explore what makes these books—and their authors—so exceptional.

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The Double Winners

1. "James" by Percival Everett (2024-2025)

Awards Won:

• National Book Award for Fiction (2024)
• Pulitzer Prize for Fiction (2025)

What It's About:

Percival Everett's "James" is a bold reimagining of Mark Twain's "The Adventures of Huckleberry Finn," told from the perspective of Jim, the enslaved man who travels down the Mississippi River with Huck.

Rather than the dialect-heavy character from Twain's novel, Everett presents Jim—who renames himself James—as an intelligent, literate man who strategically performs the role expected of him in the antebellum South. The novel explores themes of identity, freedom, and the masks people wear for survival.

Why It Won:

"James" represents a masterful literary conversation with American classics. By centering a previously marginalized character and giving him full humanity, depth, and agency, Everett creates both a powerful historical novel and a contemporary commentary on race, identity, and storytelling itself.

The novel's dual wins reflect its appeal to different literary values:

• National Book Award judges often favor innovative, contemporary voices addressing American identity
• Pulitzer Prize committees traditionally recognize works of distinguished merit that examine the American experience

"James" satisfied both criteria while offering a fresh perspective on one of America's most famous novels.

Critical Reception:

"A magnificent novel... Everett has taken a much-loved classic and transformed it into something even more profound." — The New York Times

The book dominated the 2024-2025 award season, appearing on virtually every major shortlist and winning both of America's most prestigious fiction prizes.

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2. "The Underground Railroad" by Colson Whitehead (2016-2017)

Awards Won:

• National Book Award for Fiction (2016)
• Pulitzer Prize for Fiction (2017)

What It's About:

Colson Whitehead's sixth novel reimagines the Underground Railroad as a literal underground train network running beneath the antebellum South. The story follows Cora, a young enslaved woman in Georgia, as she escapes through this fantastical railway system, encountering different states that represent various historical approaches to race and freedom.

Each state Cora passes through presents a different historical horror: from forced sterilization programs to violent race massacres to supposed utopias with dark underbellies. The novel blends magical realism with historical fiction to create an allegory about American racial history.

Why It Won:

"The Underground Railroad" achieved the rare feat of being both a critical darling and a popular success. Whitehead's decision to make the metaphorical Underground Railroad literal allowed him to compress different periods of American racial history into a single narrative journey.

The novel appealed to award committees for several reasons:

1. Innovative Form: The magical realism element distinguished it from traditional historical fiction
2. Historical Significance: It addressed America's original sin of slavery with unflinching honesty
3. Literary Craft: Whitehead's prose balances beauty with brutality
4. Contemporary Relevance: The themes resonated deeply in 2016-2017 America

Critical Reception:

"A potent, almost hallucinatory rewrite of American history... Whitehead has created one of the defining novels of this era." — The Wall Street Journal

The book was selected for Oprah's Book Club, adapted into an Amazon Prime series by Barry Jenkins, and became an international bestseller—proving that literary excellence and popular appeal aren't mutually exclusive.

Cultural Impact:

"The Underground Railroad" transcended the literary world:

• Selected by Oprah for her Book Club revival
• Adapted into an Emmy-winning limited series (2021)
• Translated into over 40 languages
• Added to high school and college curricula nationwide

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What These Books Have in Common

1. Historical Reckoning with American Race Relations

Both novels confront America's history of slavery and racial oppression head-on. They don't shy away from brutality, but they also center Black characters' humanity, intelligence, and agency in ways that challenge historical narratives.

2. Innovative Narrative Approaches

Neither book is straightforward historical realism:

• "The Underground Railroad" employs magical realism
• "James" uses metafictional dialogue with a classic text

This innovation shows award committees value fresh approaches to difficult subjects.

3. Literary Craft Meets Accessibility

Both novels are beautifully written but also page-turning narratives. They prove that literary fiction doesn't require obscurity or difficulty to achieve greatness.

4. Timing and Cultural Context

Both books arrived at culturally significant moments:

• "The Underground Railroad" (2016-2017): During intense national conversations about racial justice
• "James" (2024-2025): Amid ongoing debates about how to teach American history

5. Multiple Perspectives Appeal

These books satisfied different award committees' criteria:

• The National Book Award's focus on American voices and innovation
• The Pulitzer's emphasis on distinguished American literature

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The Author Factor: Colson Whitehead's Unprecedented Achievement

Colson Whitehead deserves special recognition as the only author to win the Pulitzer Prize for Fiction twice:

1. "The Underground Railroad" (2017)
2. "The Nickel Boys" (2020)

This places him in an extraordinarily elite club. Only four authors have ever won the Pulitzer Prize for Fiction multiple times:

• Booth Tarkington: "The Magnificent Ambersons" (1919), "Alice Adams" (1922)
• William Faulkner: "A Fable" (1955), "The Reivers" (1963)
• John Updike: "Rabbit Is Rich" (1982), "Rabbit at Rest" (1991)
• Colson Whitehead: "The Underground Railroad" (2017), "The Nickel Boys" (2020)

Whitehead is the first Black author to achieve this distinction and the first to win both Pulitzers in the 21st century.

"The Nickel Boys" (2020)

Whitehead's second Pulitzer winner tells the story of two Black teenagers at a brutal reform school in Jim Crow-era Florida, based on the real Dozier School for Boys where unmarked graves of students were discovered in 2012.

Like "The Underground Railroad," it:

• Confronts American racial violence
• Combines historical research with literary innovation
• Centers Black characters' full humanity
• Achieves both critical acclaim and popular success

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Why Are Double Winners So Rare?

Different Award Criteria

Each major literary prize has distinct values and judging processes:

National Book Award:

• Focuses on American writers
• Values innovation and contemporary voices
• Judged by a rotating panel of writers
• Awards announced in November

Pulitzer Prize:

• Open to any book published in the US
• Emphasizes "distinguished fiction by an American author, preferably dealing with American life"
• Judged by journalists and academics
• Awards announced in April/May of the following year

For a book to win both, it must satisfy multiple sets of criteria and multiple judging panels separated by months.

Timing Challenges

Awards operate on different schedules. A book published in fall might win the National Book Award that same year but compete for the Pulitzer the following spring—meaning it must maintain momentum and relevance for many months.

Competition Strength

Each year brings dozens of exceptional books. For one book to rise above strong competition in multiple award cycles requires extraordinary quality and often fortunate timing.

Genre Preferences

Different awards favor different types of fiction. Historical fiction, domestic realism, experimental fiction, and social realism all have varying appeal to different committees in different years.

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Near Misses: Books That Almost Made the List

Several books won one of these awards and were finalists for the other:

National Book Award Winners, Pulitzer Finalists:

• "Trust" by Hernan Diaz (2022 Pulitzer finalist, won NBA)
• "The Friend" by Sigrid Nunez (2018 finalist for both, won NBA)

Pulitzer Winners, National Book Award Finalists:

• "All the Light We Cannot See" by Anthony Doerr (2015 Pulitzer winner, NBA finalist)
• "The Goldfinch" by Donna Tartt (2014 Pulitzer winner, NBA longlist)

These near-misses show how difficult the double win truly is.

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Other Notable Multi-Award Achievements

While our focus is on different awards for the same book, it's worth noting authors who've won the same award multiple times:

N. K. Jemisin - Hugo Award Triple Crown

The only author ever to win the Hugo Award for Best Novel three consecutive years:

• "The Fifth Season" (2016)
• "The Obelisk Gate" (2017)
• "The Stone Sky" (2018)

Hilary Mantel - Double Booker Winner

Won the Booker Prize twice for her Thomas Cromwell trilogy:

• "Wolf Hall" (2009)
• "Bring Up the Bodies" (2012)

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Conclusion: The Rarity Makes Them Special

With only two books achieving the National Book Award + Pulitzer Prize double in the past 20 years, these winners represent the absolute pinnacle of contemporary American fiction.

"The Underground Railroad" and "James" aren't just excellent books—they're cultural touchstones that redefined how we tell stories about American history. They proved that fiction can be both artful and accessible, timely and timeless, specific in setting yet universal in resonance.

Whether you're a casual reader looking for your next great book or a literature enthusiast tracking award trends, these double winners deserve a place on your reading list.

They're not just award winners. They're modern classics in the making.

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Read These Award-Winning Books

"James" by Percival Everett

• National Book Award for Fiction (2024)
• Pulitzer Prize for Fiction (2025)

"The Underground Railroad" by Colson Whitehead

• National Book Award for Fiction (2016)
• Pulitzer Prize for Fiction (2017)

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Explore more award-winning books in our comprehensive database of 40+ literary prizes spanning 2005-2025. Search by award, year, or author at Literary Laureates.