How To—Writing the Baddies

Do you ever consider what makes up your genre? The tropes, rules, regulations? The bylaws?

No. No, I don’t get out much. But more to the point I study genre to understand what makes the underpinnings of the story. 

Romance novel heroines are a certain age, have a specific “history,” and are pretty—but they never know they are pretty. The romantic interest is older, more “experienced,” with a mysterious—but not too mysterious—past. Obvs, Charlotte Bronté didn’t get that memo. 

If I sound critical, it is analysis more than judgment. I’ve read books in just about every genre. So, as you would suspect, 99% of those books have a genre-specific blueprint. The blueprint serves both the author, (how-to guide) and the reader, (what to expect). 

Crime is my genre and it is a little more difficult to pin down. There are multiple subgenres, each with its own norms and rules. Private investigators are usually wisecracking tough guys with their own code of right/wrong. Police detectives are brilliant but could not get their personal lives together if they had Marie Kondo and three assistants. 

The serial killer is ALWAYS a genius, one step ahead of the police. Or he is an inarticulate monster who gets by on a LOT of luck. They are always (in the dozen or so books I've read) men and the victims are women.

Don’t get me started on spies and assassins. And, yes, that is crime, too.

My neck of the swamp is the baddies, the heisters, the hustlers, the dirty cops, and the smugglers. The rules are really loose. No matter how well-intentioned, the baddies typically come to tragic ends. But really, you can get by with a lot as long as it sorta makes sense and the tone is consistent.

The gospel according to Barbossa

That’s the problem, though. What makes sense? What is a consistent tone?

You ask crime fans what their favorite crime story is and you’ll get a mixed bag. Some will reference Michael Mann’s Heat. Others will call out The Wire by David Simon, et al. Some may even reference print-guys like Elmore Leonard (the Jack Foley books, especially), or Donald Westlake (Parker is the archetype heister for a lot of us). The cool kids love Patricia Highsmith’s highly-imperfect psychopath, Tom Ripley. 

Those characters thread the needle between reality and marketability. Iain Levison’s budding bad-guy, Doug, (bad-man name if I ever read one) laments that he would like to go at his heist like like De Niro and Kilmer in Heat, but the guns those guys used costs more than is netted in the typical bank robbery. Of course the flipside (true crime) can read dry as a mother’s kiss without the throughline of a plot. Levinson’s How to Rob an Armored Car nails character development, terse plot execution, and a well-oiled tone in a TIGHT 300 pages all rooted in absurd plausibility. 

So what does makes a criminal?

Another fun guy at parties

Bernie Madoff, Griselda Blanco, Neil McCauley, (the real-deal who De Niro’s Heat character was based on) all have one thing in common: working poverty. Madoff’s father was a journeyman plumber from Queens. Blanco grew up in abject poverty picking pockets and participating in kidnappings by the age of 13. Little is known about McCauley but no one spends half their life in prison—only to die on a score without some life-long hunger on them. 

“I volunteered for the army on my birthday, they draft the white trash first ‘round here anyway” -Steve Earle, Copperhead Road 

Like John Lee Pettimore, (the protagonist of Steve Earle’s Copperhead Road) many men from deep poverty went to war in Vietnam because they had few or no other options. They were trained in advanced counterinsurgency and survived by adapting and taking the initiative. But when they returned home prospects were just as scarce. 

If they found work it was menial labor for menial wages. It’s no coincidence that bank robberies spiked in the 60s and 70s. Nor is it coincidence that a lot of early drug runners were veterans unwilling to play unemployment-line games. 

“Evil is evil because you can’t understand it,” - Young-Ha Kim, Diary of a Murderer

However you must beware of trying too hard to paint a point-to-point map of your characters development. In E.L. James’ Fifty Shades of Grey, the author attempts to “explain” the protagonists kink by linking it to adolescent sexual abuse. It’s connect-the-dots trite and a little lazy. One-hundred years of clinical study has yielded one fact: we’ve only scratched the surface of human psychology and development. 

What we do know is, correlation does NOT equal causation. 

We also know: abuse is a near constant among violent offenders. Sexual abuse is a prevalent among sexual predators. However, sexual dysfunction manifests in a variety of crimes, from burglary, to arson, to bank robbery.

Not the bad man you expect, but typically the bad man you get

So, what does a bad man look like? Michael Mann’s first film was a television movie about a running prodigy who happens to be in prison for murder. While filming, Mann learned a lot from the men behind bars and his experiences informed his movies for the next 30 years. 

Neal McCauley (De Niro’s character in Heat) has nothing in his life but the next score. He lives Spartan. No momentos, no attachments—hell, he has no furniture. He doesn't even have a monologue explaining himself. Other people define what makes McCauley tick. 

When his associate, Michael Cheritto proclaims, “For me, the score is the juice,” we know that it’s the same for McCauley. The score, the one thing he's good at, is McCauley's only passion. He suffers for his art.

A sex-drive tied to danger motivates Donald Westlake’s heist-man, Parker. While Gerald Petievich’s master counterfeiter, Rick Masters only does his “paper tricks” to support his inner artist. Newton Thornburg's blackmailer, Alexander Cutter, wants revenge against the monied southern-California elite for throwing him out of the club.

Your in to your baddy is their motivation. Understand that and you understand them. Then it's just a matter of up-ending their plans and making them dance.

In that execution—taking measure of the character's world so we can snatch it out from under them—the writer is part analyst and part criminal.

All images are used for educational/instructional purposes as covered under the Fair Use Doctrine.

What Re-Reading Favorite Books can Teach the Writer

 

A few weeks ago my scribble sibling, Mike Cook and I were talking about our writing guides. Not writing manuals, mind you, but the fiction books that influenced us. Especially those books that inspired us to write. 

We all have favorite books but my question is what was your "I can do this" story? Comic book or book-book, TV show or movie, what was the story that moved you to start writing your ideas? Mike made me consider something else...

Have you revisited those inciting stories as a writing “adult”?

See, as important as great books are, reflection illuminates the imperfection and that is as important as the original flash of brilliance. Looking back on cherished books—often seeing warts and all—is key to a writers’ development. Which is what we discussed. 

Yes, we writers are a raucous bunch 

Mike spoke of Denise Lehane’s books, especially works like A Drink Before the War and Shutter Island and how much they meant to him. I’ve known of Lehane for years. I recall an interview in which he stated (and I paraphrase) that his style was strongly inspired by Robert B. Parker and that his first couple of books were written in an imitation of Parker’s voice. Of course I was intrigued and had every intention of reading his work. Then I saw Gone Baby Gone. 

I can’t speak to how closely the movie follows the book, but the resolution was distinctly “bookish.” That ending undermined the dirty honesty underpinning the rest of the story and cooled my interest in reading Lehane considerably. 

Mike spoke of enjoying Lehane’s books on first read-through. His assessment matched reviews I read of books like Mystic River and Shutter Island—rich characterizations, haunting details, cold-and-mean settings. 

And yet…

But in revisiting one of Lehane’s books, Mike stated he was dumbstruck by how much the prose differed from his memory. The first-person narrative grated on him. Especially the narrator’s obsession with his attire and/or appearance. In short, the book that he thought was so near perfect did, indeed, have flaws.

Character development: their characterizations, your development.

Anyone who’s read my little ditties for more than a minute will note multiple references to Robert B. Parker, Thomas Harris, and Donald Westlake. From my critical assessments you might infer that I don’t like Parker, Harris, or Westlake. The truth is they were each immensely influential in my development as a writer and I love each writers' work dearly.

Spenser was the first P.I. that I read after I exhausted Mickey Spillane’s Mike Hammer. Robert B. Parker’s whip-crack dialogue and evocative use of location absolutely captured my teenage imagination. Inspired for the first time to write more than superheroes, I thought Parker invented modern crime fiction. 

Again, with feeling...

And those first eight-ish books are exercises in breakneck brilliance. Hoever, by book 15, Spenser, (more grumpy-old man than biting social critic) began to chafe. By book 19, I felt confident that Parker had lost his touch. On a lark, I re-read The Godwulf Manuscript, only to be disappointed by Parker’s padding. Did we need to know the width of flare in Spenser’s trousers? 

Unsure of my assessment, I continued reading, God Save the Child and Mortal Stakes and on through Looking for Rachel Wallace. Parker hadn’t lost his touch. I had lost patience with his character. By contrast, Parker’s Jesse Stone was a breath of fresh air in narrative style. Unfortunately much of Parker’s trope-chest carried over.

Was that the big bad guy or the big good guy?

Men are either big and bad or big and good. Little men are weasilly and/or over confident. Women are…even more limited in development, either throwing their ~ahem~ feminine wiles at Spenser...or they're ugly. 

Wait, there was a woman there?

When Spenser’s long-time romantic partner, Susan Silverman strikes out to establish her own identity, the story is tremendously truncated. All we see is a frivilous little woman making silly little mistakes with big consequences. Over the course of three books, subplot to secondary plot, to main plot, the story dances close to break-up porn with Spenser proven right in all his assumptions. Then, after the break up which serves only to illustrate what a HUGE mistake Susan has made that causes no end of trouble—their seperation is NEVER mentioned again. 

Not an isolated incident

In The Red Dragon, Thomas Harris’ psychological exploration of serial killers like Francis Dolarhyde as well as FBI manhunter Will Graham, represented a shift from pulp exploitation to genuine character development. If Graham, (the hero) is underdeveloped, then Dolarhyde, (the monster) fully fleshed out. Faint glimpses of his past/damage is subtle but horrifying.

Unsatisfied, Harris stretched to write a previously unseen character—a brilliant, haunted woman, chasing the bad guy—in Silence of the Lambs. In Clarice Starling, we get a character arc that is as informative to the events as it is heart wrenchingly effective. But when Harris gets to Jame [sic] Gumb it is as if he completely lost interest. We learn more about Gumb, who remains Harris’ flattest character, from Lecter. 

A faulty device is excusable. What is Gumb, after all, if not simply a vehicle to bring Starling and Lecter together? What is not excusable is what Harris did to the LGBTQ community with Gumb. Big, scary, and menacingly gay, Gumb has done almost as much harm as Harris’ deification of the FBI, which I’ll leave right there.

"If Richard Stark, (Westlake) writes it, I read it," -Elmore Leonard

Donald Westlake, like Robert B. Parker and Thomas Harris took my limited expectations and blew my mind wide open. Also like Parker, Westlake possessed a tremendous command of brevity. A writer’s writer, Westlake (as Richard Stark, et al)  balanced the bumbling Dortmunder's absurdist humor in one hand and his master-hesiter, Parker's (obviously, no relation to the previously mentioned Parker) brutality in the other. Across his fifty-year career, spanning 100 books, Westlake's crime lingo and under-world systems have been studied by would-be writers and grad students alike. 

Taking it to the streets...just not any streets you've ever heard of

But on re-read I’m struck by how utterly illogical so much of Parker’s world is. His contacts, (motel managers, restaurant owners, etc.) are all either hustlers or retired hoods. No one ever rats Parker out for a lighter sentence or to get off the hook. No one has a kid who gets in trouble necessitating a “coin” to trade. A bunch of mobsters living in one hotel? That isn’t under close surveillance? After the Apalachin Meeting in 1957? Really?

The slang I'll give you, we all like to make up words and lingo. I'll even allow for a overly high level of organization in a world of hustlers. But the idea of just giving some guy some money for his good will is nuts. Especially when the real-life Henry Hill, (Goodfellas) spoke of borrowing and then stiffing loan sharks who were lower down on the food chain than he was.

The gift that keeps on giving.

Does that mean that I love those stories any less? Certainly not. Reading those works showed me new ways, different ways, (than taught in English lit) to tell a story. However, the more I read, the less I want to write like Parker or Harris, Westlake or Leonard. 

Rereading those stories helped me identify weaknesses in their work as well as my own. While I had to imitate those writers in early attempts to find my own voice, I did ultimately have to find my own voice to tell my own stories. That is what reading does for the writer. 

The photo above, Shutter Island movie poster, is the property of Paramount Pictures. Its use here, for educational/instructional purposes is covered by the Fair Use Doctrine.