The best novels about underdogs on a doomed mission

The Books I Picked & Why

The Spy Who Came in from the Cold

By John Le Carré

Book cover of The Spy Who Came in from the Cold

Why this book?

It’s simply a great and well-crafted story and one that grabbed me well before I knew I wanted to write. British agent Alec Leamas is burned out and believes the Cold War is over for him, but then he’s given a chance at revenge by posing as an East German defector. All the while, Western espionage methods aren’t looking any morally better than the enemy’s, and Leamas feels it. No heroes here, just underdogs and survivors—a revelation at the time. A classic for so many reasons. 

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The Talented Mr. Ripley

By Patricia Highsmith

Book cover of The Talented Mr. Ripley

Why this book?

The now (in)famous confidence man Tom Ripley debuts in this classic. Talk about an underdog and a survivor—the aspiring Ripley so desperately wants to become someone he’s not that he will do anything, murder even, to reinvent himself again and again. He’ll even assume another’s personality and own it when all seems lost. He’s one of the original bad boys whom you want to follow despite their bad deeds, and why is that? It’s because Ripley never gives up, even when he has no clue what’s next. 

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True Grit

By Charles Portis

Book cover of True Grit

Why this book?

Who can’t love the main character Mattie Ross? Young Mattie has one of the best voices in fiction. She’s just fourteen when a coward shoots her dad dead and takes his horse and $150. Mattie’s not going to let that go unpunished. She leaves home to take revenge, teams up with tough US Marshal Rooster Cogburn, and pursues the killer into Indian Territory. Mattie should be way in over her head and is. But Mattie’s always the boss. Charles Portis tells the headstrong Mattie’s quest in an engaging first-person style and fills the story with great historical details. 

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Going After Cacciato

By Tim O'Brien

Book cover of Going After Cacciato

Why this book?

I didn’t love this book at first, but it’s grown on me as a deceptively inventive anti-war novel. One day, frustrated GI Paul Berlin resolves to walk away from the Vietnam War—by walking in a straight line. His journey takes him from the jungles of Southeast Asia to India to the streets of Paris. It’s a sometimes puzzling ride and about so much more than going AWOL that it has to be experienced. Tim O’Brien gets away with tricking the reader, but by the time you realize it, you probably don’t care as it’s the ultimate desperate escape.

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The Honest Spy

By Andreas Kollender, Steve Anderson

Book cover of The Honest Spy

Why this book?

This is the improbable story of a true underdog who will stop at nothing to fight fascist evil, even when he has no idea what he’s doing and no one to help him. It’s also a true story. In WWII, Fritz Kolbe was a nondescript German official in the Berlin Foreign Office who made himself into a crucial spy against the Nazis yet for years remained an unknown and unsung hero. Kolbe’s dark drive and passion are fictionalized brilliantly by Andreas Kollender. I was so taken by this tale that I translated it myself from the original German. 

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