But in his stories of the lowlife gangster milieu of the Roaring Twenties and the Great Depression — the snatchers and the shooters, the dimwits and the dolls, the potatoes and the players in Broadway’s “hardened artery” — Damon Runyon invented the main character of the late twentieth century: the good bad guy.

We’re so steeped now in anti-heroes that it hardly seems bold or daring for a writer to dive into the beating heart of a man who kills or kidnaps for money. Badly behaved men — and they are usually men — as the half-sympathetic moral centre of a story have been a staple of serious literature since the Fifties: amoral murderers like Patricia Highsmith’s Tom Ripley; everyman adulterers like John Updike’s “Rabbit” Angstrom; and distilled misanthropists like Joseph Heller’s Bob Slocum (“The world just doesn’t work. It’s an idea whose time is gone”).

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.

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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.

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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.

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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.

In books, failure beats success: we all like a bit of schadenfreude, and it is frankly easier to write about loss and adversity than about life as a frictionless track. “Happiness writes with white ink on white pages,” according to the French playwright and essayist Henry de Montherlant, who at least gave his obituarists something to work with when he shot himself in the throat.

One writer of the 20th century captured both success and failure in a way that characterised not just his writing but his life and death. F. Scott Fitzgerald died 80 years ago today, suddenly, from a heart attack at the age of 44. To understand the man we need to remember the importance of aspiration in his life: it took him to Princeton University, to homes in Manhattan’s Upper West Side and Long Island, to hobnobbing on the Riviera with Picasso and Cole Porter, and into marriage to society beauty Zelda Sayre.

In the late 1930s, Fitzgerald earned $91,000 in 18 months – $1.6m today. Yet he died believing himself a failure (“My God I am a forgotten man,” he wrote to Zelda months before his death), and the newspapers agreed. He was, as the Chicago Daily News put it at the time, “almost as remote from contemporary interest as the authors of the blue-chip stock certificates of 1929”. As a hack in his final years, “he was still writing good copy, but no one was mistaking a story writer for the Herald of an Era”.

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With his success as an early chronicler, therefore effective creator, of the Jazz Age – the Herald of an Era after all – Fitzgerald was able to buy his way into the lifestyle he had always longed for. It was an ambivalent adoration: he wrote that even with “the jingle of money in his pocket”, he “would always cherish an abiding distrust, an animosity, toward the leisure class”. Nonetheless, he worked “for money with which to share their mobility and the grace that some of them had brought into their lives”. The early success of his smash hit debut novel This Side of Paradise (1920) brought him to a world of “ineffable toploftiness and promise” and instilled in him the conviction, never quite eradicated, that “life is a romantic affair”. Yet within a couple of years he was an alcoholic, and his marriage punctuated with bust ups.

The balancing act of success and failure would follow throughout his life, and is given its finest artistic expression in his greatest and best-loved novel The Great Gatsby, published in 1925. Gatsby is a story of failure masquerading as success, about a man who invented his own past to win the love of a woman whose “voice is full of money”. The love is doomed, of course – romantically so – though that hasn’t stopped the modern appropriation of Gatsby as a sexy glamour theme for parties, by people who have forgotten or never knew that the story culminates in a car crash with a woman killed and her breast torn off, “swinging loose like a flap”.

By the 1930s, though, Fitzgerald was no longer a hot name — he had taken nine years to follow up The Great Gatsby with Tender is the Night, and the book had a mixed reception — and he descended into a period of alcoholic depression where he “cracked like an old plate”.

Fitzgerald took himself to Hollywood to earn his way out of debt. And for a time it worked: at his height he was earning $1,250 a week (almost $25,000 today), but by 1939 he was out of contract and fighting for scraps as a freelancer, and the royalties for his books were $13. To the writer Budd Schulberg, who worked on a script with him until they were both fired after two days of drinking, Fitzgerald had a “manuscript white” complexion, “the Ghost of the Great Novelist Past”.

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Yet even here Fitzgerald was able to snatch success from the jaws of failure. At the weekends he wrote stories about a new character called Pat Hobby: a washed-up, alcoholic scriptwriter. And they are wonderful, easily his most purely pleasurable fictions, light and funny and sad despite being written in the last year of his life and under the drive, as ever, of the need for cash. He sold them to Esquire, his cable messages to his editor ever plaintive: “Again, the old ache of money. Again, will you wire me if you like it.” “I wish to God you could pay more money.”

The man who saw his life characterised by “some sort of epic grandeur” struggled to live up to his own vision, repeatedly turning success into failure and failure into success. Knocked by critics for his obsession with writing about aspiration and loss, he responded, “But, my God! It was my material, and it was all I had to deal with.” His greatest and final reversal was the slow turnaround in his posthumous reputation so that now, 80 years after his death and 95 after Gatsby, Fitzgerald finally enjoys the impregnable literary reputation that eluded him in life.

Yet part of Fitzgerald’s appeal lies in the very failures that caused him such suffering: do we view him as all the more heroic for battling through his dips and troughs, or are we really congratulating ourselves for his posthumous resurrection? There is a connection, I think, to the literary world’s scepticism toward success and a corresponding weakness for failure, partly a refraction of what Martin Amis called the “intellectual glamour to gloom” and partly from a constitutional suspicion of materialism and commerce, our most dominant cultural markers of success.

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In the literature of the 20th century, the life of a man of business (it was invariably a man) was worthy of contemplation only if it exposed the hollowness of his capitalist world, as seen in a rich vein of novels from Sinclair Lewis’s Babbitt (1922) through Sloan Wilson’s The Man in the Gray Flannel Suit (1955) and Richard Yates’s Revolutionary Road (1961). This trend reached its apotheosis in Joseph Heller’s misanthropic masterpiece Something Happened (1974) with its refrain “The world just doesn’t work. It’s an idea whose time is gone,” after which there was nothing left to say – though that didn’t stop lesser writers from trying.

This mistrust of success can go further. In literature, as in politics, ideas move from the fringes to the centre, which is why the work of small presses in finding new voices is celebrated. But this is sometimes accompanied by a disdain for the commercial success of mainstream publishing, which acts like a Premier League, snapping up the most popular of the writers discovered out at the edges.

This suspicion is misguided, given that success and failure are dependent on one another. Literature tends to see itself as countercultural, uninterested in bourgeois concepts like ambition. But to believe in its continued prosperity outside any commercial imperatives requires a wilful blindness that is… well, that is pretty common, to be honest, in our contemporary world of groupthink, filter bubbles and echo chambers. Fitzgerald might have foreseen this when he wrote of Gatsby that a key force in the novel is “those illusions that give such colour to the world that you don’t care whether things are true or false as long as they partake of the magical glory”.