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.