I was watching an old Humphrey Bogart film the other day – HIGH SIERRA, from 1941 – and it got me thinking about the portrayals of good and bad in stories. Not only that, I started thinking about some of my favourite stories, and why I like them.

One of the things they had in common? Morally ambiguous characters.

Roy Earle, Bogart’s character in the film, is a hardened criminal. He’s released from prison and hired to help pull off a high stakes robbery of a resort in California. Should be easy, right? As was standard in films, he even looked the part: dark clothes, a scowl, and his lines delivered with the right amount of toughness. Except… it’s just not that easy. Roy Earle is humanized for the viewer with his desire for Velma, the charming young woman with a club foot. He even dreams of marrying her. He adopts a dog, Pard, while waiting around for the heist to go off. And most tellingly, he hooks up with a street-smart taxi dancer named Marie, telling her time and again that she doesn’t mean anything to him, and that if the going got tough, he’d have to park her. However, his actions belie his words and he takes care of her and tries, albeit awkwardly, to make her happy.

It would be hard for a film-goer to have any sympathy for the gangsters portrayed in the 1930s by Cagney, Robinson, and Paul Muni, but Bogart’s Roy Earle was a game-changer in the world of film. Audiences were rooting for the man that, not even five years earlier, would have been portrayed solely as a heartless killer.

If a villain has been written as soulless and unquestionably evil, my interest in the story will quickly wane. Even Lasher, in Anne Rice’s novel THE WITCHING HOUR, wasn’t all bad. His goal was destructive to others, but his desire for that goal was entirely human and understandable. Rowan, the lauded neurosurgeon with her life-saving powers, is not the knight on the white charger. The decisions she makes are just as flawed, just as human, as anyone else’s would be.

Humanizing the villain, giving them an opportunity to be in conflict with themselves instead of just with your hero, goes a long way towards making a story linger after the last page has been turned.