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How To Write A Pulitzer Prize Winning Novel starring… The Underground Railroad by Colson Whitehead

October 18, 2020

The Underground Railroad by Colson Whitehead is a tough book to check out from the public library. The waiting time is long, and even before the lockdowns began, borrowers rarely returned it.

I finally had enough, so I bought a cheap copy at a used book store last week. I haven’t finished reading it, but I can already tell why it received a Pulitzer Prize for Fiction in 2016.

1. Emotional setting.

Setting is huge in a lot of Pulitzers. This one is set in the South before the Civil War, and slavery is a huge emotional topic in the United States. Some people get angry that slavery existed in the United States, and others get angry that they didn’t get to profit from it. Either way, people get emotional.

Write about an emotional/pivotal time period in the United States, and you have an advantage over other writers.

2. Sympathetic main character

The main character in The Underground Railroad is a slave who decides to flee, even though it comes with a price. Everybody sympathizes with a slave. Even descendants of slave owners sympathize with slaves. You have to be a dick of a reader not to sympathize with a slave who escapes.

The Underground Railroad probably wouldn’t have received a Pulitzer if it had been told from the slaveowner’s point-of-view. Not unless he/she was a really sympathetic slaveowner.

3. Traumatic experiences

The Pulitzer judges love traumatic experiences, but don’t overdo it. Don’t get too graphic or extreme. To be fair, I haven’t read much of The Underground Railroad yet, so I don’t know how traumatic the experiences will be, but a book about slavery has to have trauma.

Readers will actually get angry if a book about slavery doesn’t have a little bit of trauma. It would almost be like false advertising.

4. One cool idea.

According to every history book I’ve read, The Underground Railroad wasn’t really a railroad and it wasn’t physically underground. Colson Whitehead’s cool idea for The Underground Railroad was to take that metaphor of an underground railroad and make it literal.

That’s all it takes: one cool idea. I just hope no lazy high school students take a history test after reading the novel.

Using these devices don’t guarantee a writer a Pulitzer, especially if a bunch of other authors do the same thing. Plus, not every Pulitzer uses the same elements. All The Light We Cannot See by Anthony Doerr uses a similar formula, and I’m guessing The Sympathizer by Viet Thanh Nguyen does as well (I could be wrong).

Other Pulitzers, like A Visit from the Goon Squad by Jennifer Egan or Less (Ugh… Less) by some author whose name I don’t want to look up, use different strategies, so there is more than one way to write a Pulitzer Prize winning novel.

But if your goal is to win a Pulitzer Prize for Fiction (that’s not my goal, by the way), these four elements provide a good start.


What do you think? What does it take to win a Pulitzer Prize for Fiction? What did you think of The Underground Railroad?

  1. Hi, I loved The Underground Railroad and I loved The Nickel Boys even more. You’ve mentioned a lot of the qualities of an award-winning book. I haven’t read all the Pulitzers but unlike you, I liked Less very much! All the Light We Cannot See is also one of my favorite Pulitzer Prize winners. Did you ever read The Shipping News? I liked it, but many of my friends did not. It was very different, which also seems to be a feature of the prize winners.

    • No, I haven’t read much of The Shipping News. A guy in my writer’s group in the 1990s loved that book, so I tried it then but couldn’t get into it. My tastes have changed since then, so I might try it again.

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