The best novels about underdogs on a doomed mission

Who am I?

I’m drawn to characters who are stuck between two worlds and in over their heads and doomed to fail, but they stick with it anyway. My novels also tend to include overlooked historical themes from the WWII and Cold War eras, often involving espionage or crime. I have an MA in history, so I like researching and using historical detail to dramatize the story. I’ve also been a Fulbright Fellow, a fiction editor, and a translator of German fiction. The books on this list all include the type of underdogs that I love—and inspired my work. 


I wrote...

The Losing Role

By Steve Anderson,

Book cover of The Losing Role

What is my book about?

When the SS orders struggling German actor Max Kaspar to impersonate a US officer during the bloody Battle of the Bulge, Max devises his own secret mission to escape the war and flee to America. 

It’s both his one big break and a deadly last chance on a journey that’s taken him from a once-promising career to brutal front-line combat. But his mission is doomed from the start. Trapped between the brutal front lines, he must summon all his acting talents and newfound courage to evade perilous traps laid by both sides. The desperate special operation in my story is inspired by a real-life WWII operation. 

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The books I picked & why

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. 

The Spy Who Came in From the Cold

By John le Carré,

Why should I read it?

10 authors picked The Spy Who Came in From the Cold as one of their favorite books, and they share why you should read it.

What is this book about?

From the New York Times bestselling author of Tinker, Tailor, Soldier, Spy; Our Kind of Traitor; and The Night Manager, now a television series starring Tom Hiddleston.

The 50th-anniversary edition of the bestselling novel that launched John le Carre's career worldwide

In the shadow of the newly erected Berlin Wall, Alec Leamas watches as his last agent is shot dead by East German sentries. For Leamas, the head of Berlin Station, the Cold War is over. As he faces the prospect of retirement or worse-a desk job-Control offers him a unique opportunity for revenge. Assuming the guise of an embittered…


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. 

The Talented Mr. Ripley

By Patricia Highsmith,

Why should I read it?

12 authors picked The Talented Mr. Ripley as one of their favorite books, and they share why you should read it.

What is this book about?

It's here, in the first volume of Patricia Highsmith's five-book Ripley series, that we are introduced to the suave Tom Ripley, a young striver seeking to leave behind his past as an orphan bullied for being a "sissy." Newly arrived in the heady world of Manhattan, Ripley meets a wealthy industrialist who hires him to bring his playboy son, Dickie Greenleaf, back from gallivanting in Italy. Soon Ripley's fascination with Dickie's debonair lifestyle turns obsessive as he finds himself enraged by Dickie's ambivalent affections for Marge, a charming American dilettante, and Ripley begins a deadly game. "Sinister and strangely alluring"…


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. 

True Grit

By Charles Portis,

Why should I read it?

14 authors picked True Grit as one of their favorite books, and they share why you should read it.

What is this book about?

There is no knowing what lies in a man's heart. On a trip to buy ponies, Frank Ross is killed by one of his own workers. Tom Chaney shoots him down in the street for a horse, $150 cash, and two Californian gold pieces. Ross's unusually mature and single-minded fourteen-year-old daughter Mattie travels to claim his body, and finds that the authorities are doing nothing to find Chaney. Then she hears of Rooster - a man, she's told, who has grit - and convinces him to join her in a quest into dark, dangerous Indian territory to hunt Chaney down…


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.

Going After Cacciato

By Tim O'Brien,

Why should I read it?

3 authors picked Going After Cacciato as one of their favorite books, and they share why you should read it.

What is this book about?

Winner of the National Book Award, 'Going After Cacciato' captures the peculiar mixture of horror and hallucination that marked the Vietnam War, this strangest of wars.

In a blend of reality and fantasy, this novel tells the story of a young soldier who one day lays down his rifle and sets off on a quixotic journey from the jungles of Indochina to the streets of Paris.

In its memorable evocation of men both fleeing from and meeting the demands of battle, 'Going After Cacciato' stands as much more than just a great war novel. Ultimately it's about the forces of…


The Honest Spy

By Andreas Kollender, Steve Anderson (translator),

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. 

The Honest Spy

By Andreas Kollender, Steve Anderson (translator),

Why should I read it?

1 author picked The Honest Spy as one of their favorite books, and they share why you should read it.

What is this book about?

During one of history's darkest chapters, one man is determined to make a difference.

In the tradition of Schindler's List comes a thrilling novel based on the heroic true story of Fritz Kolbe, a widowed civil servant in Adolf Hitler's foreign ministry. Recognizing that millions of lives are at stake, Kolbe uses his position to pass information to the Americans-risking himself and the people he holds most dear-and embarks on a dangerous double life as the Allies' most important spy.

Summoned from his South African post to return to Nazi Germany, Kolbe leaves behind his beloved fourteen-year-old daughter, a decision…


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