Expert Reviews & Insights

Heists, Cons, and Clever Criminals: Crime Fiction Where the Bad Guys Win

Explore the morally ambiguous world of crime fiction where charismatic criminals, daring heists, and lovable con artists take center stage in stories that make you root for the underdog.

Reviewed By
Simon Chance

There is a specific, adrenaline-fueled joy found in watching a perfectly constructed plan unfold. In the world of crime fiction, we often find ourselves aligned with the detectives and the do-gooders, but there is an undeniable allure to the other side of the law. Why do we root for the bank robber, the con artist, or the getaway driver? Perhaps it is the David and Goliath theme that resonates so deeply; the idea of a ramshackle group of mismatched outsiders taking a slice of the pie from a corrupt institution.

In these stories, morality is not a spectrum of black and white, but a murky, fascinating gray. We are challenged to confront truths about human nature and the strict definitions of good and evil. Whether motivated by revenge, survival, or a desire to right historical wrongs, the anti-heroes in the following novels compel us to become their accomplices, if only for a few hundred pages. Here are five essential reads where the bad guys steal the show.

Portrait of a Thief by Grace D. Li

The heist genre often revolves around monetary greed, but Grace D. Li's instant New York Times bestseller, Portrait of a Thief, raises the stakes by introducing a profound motivation: the reclamation of culture. The story follows five young Chinese Americans who are hired to steal back looted art from world-class museums. This is not just a caper; it is a commentary on the legacy of colonialism.

Li crafts a narrative that feels like a modern blockbuster—drawing comparisons to Ocean's Eleven—but grounds it in the very real, complex identities of her protagonists. They are motivated by a $50 million reward, certainly, but they are driven by a deeper desire to address historical injustices. Readers are treated to a story that is as intellectually stimulating as it is suspenseful. The characters are indelible, and the anti-colonialist message adds a layer of depth that elevates the genre far beyond a simple grab-and-go thrill ride.

Buy Portrait of a Thief at Amazon

Blacktop Wasteland by S. A. Cosby

If you are looking for a gritty, high-octane thrill ride, S. A. Cosby’s Blacktop Wasteland is a modern masterpiece of Southern noir. The protagonist, Beauregard "Bug" Montage, is a man trying desperately to leave his past behind. A skilled mechanic and a former getaway driver, Bug is pushed to the brink by financial ruin and the need to protect his family. This is a story of desperation, where the "bad guy" is a loving father forced into a corner by poverty, race, and systemic barriers.

Cosby writes with a searing, operatic intensity. The driving scenes are electric, described with such visceral detail that you can practically smell the burning rubber and gasoline. Yet, it is the emotional weight of Bug’s journey that lingers long after the engine cools. We root for him not because he is a criminal, but because he is a man fighting for his dignity and his children's future in a world that offers him few legitimate paths to success. It is a compelling look at the choices people make when their backs are against the wall.

Buy Blacktop Wasteland at Amazon

The Talented Mr. Ripley by Patricia Highsmith

No list of con artists would be complete without the inclusion of Tom Ripley. Patricia Highsmith’s classic novel introduces us to one of the most chillingly charismatic sociopaths in literature. Unlike the sympathetic anti-heroes who rob from the rich to feed the poor, Ripley is driven by envy, entitlement, and obsession. He agrees to travel to Italy to retrieve a wealthy acquaintance, Dickie Greenleaf, but soon decides he would rather be Dickie Greenleaf.

What makes this novel a foundational text in the genre is how Highsmith expertly manipulates the reader. We are privy to Ripley's internal logic, his insecurities, and his terrifying adaptability. As his web of lies tightens and the body count rises, we find ourselves in the uncomfortable position of hoping he doesn't get caught. It is a psychological masterclass in perspective and the fluid nature of identity, proving that sometimes the most dangerous criminals are the ones who can blend perfectly into polite society.

Buy The Talented Mr. Ripley at Amazon

Six of Crows by Leigh Bardugo

Stepping into the realm of fantasy, Leigh Bardugo’s Six of Crows offers one of the most compelling ensemble casts in modern fiction. Set in the bustling, dangerous city of Ketterdam, the story follows teenage gang leader Kaz Brekker. Kaz is a thief with a strict, unconventional moral code who gathers a crew of outcasts for a deadly, impossible heist. The team includes a spy, a sharpshooter, a convict, and a magic-user, each with their own tragic backstory and unique skillset.

This novel exemplifies the "found family" trope that is so prevalent in heist fiction. These characters are broken people who find strength and purpose in one another. The intricate plotting of the heist is satisfyingly complex, filled with twists and clever maneuvers, but the true heart of the book lies in the sharp banter and the fierce loyalty between these "bad" guys. Bardugo proves that you don't need to be a lawful citizen to be a hero to your friends.

Buy Six of Crows at Amazon

The Little Old Lady Who Broke All the Rules by Catharina Ingelman-Sundberg

Crime fiction doesn't always have to be dark, gritty, or blood-soaked. Sometimes, it can be delightfully subversive and humorous. In this Swedish bestseller, the criminals are a group of senior citizens fed up with the poor conditions and new management at their retirement home. Martha and her friends decide that prison might actually offer a better quality of life than the "Diamond Home," so they embark on a crime spree, including a heist at the National Museum.

This novel captures the whimsical side of the genre while still delivering a solid caper. It reminds us that the desire for agency, respect, and excitement doesn't fade with age. Readers will find themselves cheering for this "League of Pensioners" as they outsmart the authorities and demand the respect—and better food—they deserve. It is a spirited adventure that proves it is never too late to break a few rules and raise some hell.

Buy The Little Old Lady Who Broke All the Rules at Amazon

Conclusion

Whether they are stealing art to fight colonialism, driving getaway cars to save their families, or conning their way into high society, these characters remind us that the line between hero and villain is often a matter of perspective. These novels offer a safe harbor to explore our darker impulses, allowing us to revel in the thrill of the heist and the satisfaction of the con, all while safely curled up with a good book.

ChoiceScout participates in the Amazon Associate program. Our links to Amazon may be affiliate links.

Check out more top reviews here.