Why do we love gangsters? Damon Runyon invented the good bad guy

The good bad guy moved from literature to film in the Seventies, and two decades later came into our homes on TV. You don’t have to look far to see the flowering of this quality in our culture. Indeed, it’s not going too far to say that without Runyon, there would be no Godfather, no Tony Soprano. Martin Scorsese would still be trying to think of something to make films about.

But when Runyon wrote his stories in the Thirties and Forties, he was bringing us news, softening us up for the century to come. He made us fall for the guy who is dubious in business and negligent in his home life and his love life.

The stand-out quality of both Runyon and his characters is that they’re funny. Runyon’s anonymous narrator is a lower-rent, warier version of P. G. Wodehouse’s tireless storyteller Mr Mulliner, and indeed Wodehouse is the writer Runyon most resembles stylistically. His rhythmic patter fits Wodehouse’s description of his own work as a “musical comedy without music”.

Runyon’s narrator trades in nicknames, neologisms, mock-formality, a language devoid of contractions and a perpetual present tense. When he tells us that “when Dave the Dude takes a guy out for an airing, the guy very often does not come back”, the threat is softened by the stilted idiom — but not too much. The same goes for the cracking line, “I always take a gander at a doll’s feet and ankles before I start handicapping her”.

Comedy lowers the reader’s guard and enables the writer to slip in other things. We get unexpected moral complexity, in the story The Lily of St Pierre, in which a tragic woman suffers a death “that happens to a million dolls before and will happen to a million dolls again”. And there is a truly psychopathic viciousness in Sense of Humour, which begins with the aptly-named Frankie the Ferocious killing the family members of an associate who played a practical joke on him, and gets worse from there.

Runyon used comedy as a balance to danger, then; his inheritors developed this, using it as a source of danger, too. In the famous scene in Scorsese’s Goodfellas, Joe Pesci’s Tommy turns laughter — “Do I amuse you?” — into blood-chilling fear. Like Runyon’s stories, like any good portrayal of the good bad guy — like any good art — it operates in multiple registers.

Connected to this is another strength of Runyon’s good bad guy: he is real. Runyon certainly knew the world he wrote about, both from his work as a newspaper reporter covering sports, politics and murder (which he called “the main event”) and from personal connections: he knew, among others, Al Capone. His portrayal of gangster culture in his stories was an exaggeration, usually for comic purposes, but it’s the authenticity that provides the frisson: Runyon’s biographer said any decent New York detective would recognise most of the crooks in his fiction, from Harry the Horse to Nicely-Nicely Johnson.

And so reading about, or watching, a good bad guy is like a rollercoaster ride: a brush with danger within a safe environment, all the more so when we are strapped to his viewpoint. We can’t help but come round to his way of thinking when we watch the serial killer’s serial killer Dexter Morgan in Dexter, or read Alex’s own words in A Clockwork Orange. After all, to paraphrase one Runyon character, many legitimate guys like you are interested in the doings of tough guys.

The guys and dolls come and go in Runyon’s stories, but his world is held together by that constant narrator, a bystander to the action (“I am known to one and all as a guy who is just around”) who rubs comfortably alongside the criminal underworld, even if he is not strictly part of it, and gently expresses theoretical disapproval of, say, kidnapping. “Snatching is by no means a high-class business, and is even considered somewhat illegal.” (Then again, we get the sense that he would help out if they were busy, and occasionally he provides a turning point in one of Runyon’s clockwork plots.) But the intimacy of the first person narrative makes us want Jo-jo and Spanish John and Dave the Dude to succeed — because reading is an act of empathy, but also because we see them within their own community, where they don’t seem so bad at all. They are, like Puzo’s mafiosi in The Godfather, bound by their own code of honour, however twisted.

The novelist Howard Spring summed up this appeal by describing Runyon’s people as “jungle-dwellers, hateful and horrible men and women, who yet please us because they are alive and completely integrated.” Fictional violence, in other words, is thrilling, and all the more so when we’re made to care about the characters dishing it out. In The Sopranos, the most simultaneously beloved and bloodthirsty of Tony’s henchmen was Paulie Walnuts, who murdered more people than anyone else, but was also a comic figure, cladding his furniture in plastic and forever repeating his jokes to impress Tony. In Scorsese’s Gangs of New York, when Daniel Day Lewis’s Bill the Butcher delivers a theatrical “Whoopsy-daisy!” as he “misses” while chucking his knives at Cameron Diaz’s Jenny, we feel the same sense of uneasily disrupted danger that Runyon detonates in his darker stories.

In capturing the Broadway gangster era, Runyon created it, just as Fitzgerald did the Jazz Age — which operated at the same time but in a different world. But Runyon’s influence goes even further: he prefigures the wisecracking Noo Yawk idiom of countless sitcoms. And by offering a gangster environment that was fundamentally comic in nature, he opened a gap between his creations and the traditional villain for others to fill, and fill it they did, forming characters who flatter our appetite for complexity by being good only in parts.

After Runyon’s death in 1946 — from a lifelong smoker’s throat cancer — a plane was flown above Manhattan and his ashes were scattered over Broadway, the avenue he dusted with his own peculiar genius. It was a tribute befitting either a city grandee or a legendary crime boss — and therefore perfect for the man who in straddling both worlds created his own, and laid the path for ours.

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John Self is a literary critic. He lives in Belfast.

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