The best literary novels that taught me valuable lessons to use as a crime writer

Lolita isn’t usually thought of as a crime novel but it is.

Thirty-seven-year-old Humbert Humbert stalks 12-year-old Lolita, then breaks all kinds of laws, moral, ethical, and legal, as he transports her across state lines.

The first time I read Lolita, I was dazzled by Nabokov’s stunning use of language—and remember, English was not his native tongue—word-play, and his ability to create full-blooded characters that leap off the page.

Nabokov pulls off this morally compromised tale with wit and humor, while dealing with the serious topic of pedophilia.

Reading Lolita gave me license to create morally challenged characters like Francis Hoyt, one of the protagonists in my novels.

Nabokov proved you don’t have to like, admire, or even feel a kinship with a character, so long as that character is interesting and compelling enough that readers are fascinated about him or her without being turned off.

I grew up on Manhattan’s Upper East Side. We lived above an all-purpose drugstore that included two aisles of paperback books.

Almost every day after school, that store became my own personal library. If were attracted by a particular title or cover, it would wind up in my to-buy list.

Seize the Day was one of those books. The protagonist is the hapless Tommy Wilhelm, a small-time loser who spends his life trying to impress his big-shot father (think Willie Loman only less successful).

Desperately trying to make something of himself that his father can be proud of, Wilhelm gets involved with conman father figure Tamkin.

What impressed me most was Bellow’s ability to create a living, breathing, deeply flawed character that you’re actually rooting for.

What makes characters like Wilhelm compelling is not only the constant struggle to survive in a world that seems to be stacked against them. Bellow recreates the world of the Upper West Side so painstakingly that it becomes another character in the book.

From Bellow I not only learned how to build a character from the inside-out, but how important geography is in a novel.

Portnoy’s Complaint is really just a long, drawn-out, hilarious, often shocking monologue which would seem an unlikely model for a crime writer.

After all, masturbation is hardly a criminal offense—at least not yet. But Roth brings so much to the table in terms of creating character through voice.

I tend to write in the first-person and reading Roth is a master class in the use of the first person.

In my book, for instance, the story is told through the eyes of three different characters. The challenge was to create three, distinct voices, all of whom have to move the action forward.

For me, Roth’s Alexander Portnoy is a perfect example of how important it is to have a compelling voice tell your story.

I first read The Naked and the Dead in a college course covering modern American fiction after World War II.

It was Mailer’s first novel and is recognized as one of the best novels to come out of a writer’s own war experiences (amazingly, Red Badge of Courage, was written by Stephen Crane, without benefit of ever experiencing war first-hand).

You’d think it would have little influence for a crime writer but it does. If you haven’t read the book and intend to, it’s time for a spoiler alert.

One of the main characters is Lt. Hearn, but halfway through the novel, Mailer does the unthinkable. He kills off one of his main characters.

Why in the world would Mailer do something like this? The answer, of course, is that he was mimicking the war experience.

War is unpredictable, especially in terms of who lives and who dies. The lesson I took from this was shocking death, was to examine the life and death powers a writer can wield. 

We can manipulate the reader (in a good way, I think) and doing the unexpected, like killing off a major character, keeps the reader off-balance.

Life is messy, as is good art, in my opinion. Mailer taught me a valuable lesson. When things are going too well, or the plot becomes predictable, it’s a good idea to throw a hand grenade into the scene, to keep the reader on his or her toes.  

Like many of us, I’m fascinated by the Old West (maybe it’s all those cowboy shows and movies I watched as a kid).

The novel follows legendary Dalton Brothers gang (related to the Younger brothers who ran with Jesse and Frank James). I stumbled across Desperadoes, which artfully co-mingles truth and fiction.

Hansen uses the conceit of having a novel told in the form of a fictional memoir, written in 1937 by 65-year-old Emmett Dalton, the last surviving member of the infamous gang.

Hansen centers his action around the gang’s plot to rob two banks in Coffeyville, Kansas, and it’s a master class in the art of blending fact and fiction.

It’s something I’ve tried to do in my book, which incorporates into the plot an actual plot to knock over a “mob bank,” backed by a real-life New England mob boss.