The best character-driven gangster novels

This book was my first foray into the world of gangsters.

Set just after World War Two in the dangerous alleys of the nascent American Mafia, The Godfather tells the story of the first family of American gangster fiction, their fight for survival, and bid for power.

The complex, indelibly drawn characters, including Vito Corleone, his three sons and their families, and “business associates” travel a bloody road of passion and power, conspiracy and crime.

This fictional family, the novel, films, and franchise have been part of my consciousness for as long as I can remember.

It’s not the best written novel on this list, but it may be the best-known, most influential crime novel ever, and that’s reason enough to read it. Capisce?

Retired hitman Frankie Machianno thinks he’s left the past behind and can focus on the things that matter—wife, mistress, daughter, surfing, perfect kitchen, roasting coffee, cooking.

But someone is coming for him and wants him dead. The problem is: Frankie doesn’t know who. As he tries to figure it out, we learn about Frank, his family, his lover, and his past, from San Diego beach bum to mafia “button man.”

He’s my favorite kind of gangster—the good guy bad guy—and I couldn’t help but like Frank and fear for his life, as the novel hurtles toward its bittersweet conclusion.



A history of the early 1960s in America, leading up to the assassination of JFK, seen through the eyes of the mobsters and criminals, crooked cops, spies, and sleazos who power the machines of history.

A comprehensive romp through the underbelly of American crime and politics (and you might, after reading this book, wonder what’s the difference), it’s a novel about characters you don’t like—but they’re vivid and fascinating.

Much more than a gritty gangster novel, it’s a tale about the people in history’s shadows, and, ultimately, history and the “never innocent” America itself. 


Few writers inhabit history, distill it, and convey the feeling of an era with the verve or immediacy of E.L. Doctorow.

In Billy Bathgate, he trains his lens on the 1930s and introduces us to Billy Behan, a fatherless Irish-Jewish kid from the Bronx, who has a chance encounter with New York gangster Dutch Schultz and decides “whatever my life was going to be in this world it would have something to do with Mr. Schultz.”

Add a love triangle, a colorful cast of mobsters, murder, blackmail, a special prosecutor, and you have the propulsive plot and rich characters that power this unforgettable novel.   

The gangsters in Kevin Barry’s vibrant, poetic novel are past their prime.

Their glory days behind them, Maurice Hearne and Charlie Redmond are now in the ferry terminal of the Spanish port of Algeciras waiting for a boat and looking for Hearne’s missing, estranged daughter. They talk, they reminisce, they question locals, they drink.

Sound boring? It’s not. Imagine two aging, Irish, very loquacious Tony Sopranos in Waiting for Godot, told in beautiful, luminous prose—and you’ll have an idea of the magic that is Kevin Barry’s unforgettable novel.