Though Runyon is still in print, and still read, he has in recent years slipped into the netherland of ancient boozy anecdote and old photographs where newspapermen of his vintage end up. He died when Jackson Pollock was already painting, but he feels as remote as Thomas Nast. The best book about Runyon is Jimmy Breslin’s slightly dispiriting biography, published in 1991, one of those “matches” that make a publisher feel wonderful until the manuscript comes in. Writers train for one length or another, and Breslin’s is essentially a series of eight-hundred-word columns strung together, all told in that good Breslin style, where this guy said that to this other guy—quick glimpses of Prohibition, the Hearst press, stealing coats in the Depression—so that the total effect is like watching the world’s longest subway train go by at night. Still, there is something more in Runyon, one feels on rereading him, than just old jokes and columns and nostalgia for “Runyonland.” Pete Hamill, another newspaperman turned novelist, has written a lovely introduction to the best current collection of Runyon, “Guys and Dolls and Other Writings,” emphasizing the artistry that it took to make funny stories from the resistant material at hand. And there is something genuinely artful, not just artisanal, in his writing. Musical comedies work by creating circumstances in which people can sing their loves and dreams. A kind of love and a kind of dream, deeper than might be apparent, must run through Runyon’s writing to make it sing so well.

By a cosmic coincidence, Damon Runyon was born in Manhattan, but it was Manhattan, Kansas—as though God were giving him the right birthplace for the obit but keeping him away from his true home until he was ready. The young Runyon actually grew up in Colorado, and stayed there until he was thirty. The Colorado-Manhattan connection in that period is so singular as to look almost significant: the newspaperman Gene Fowler, who was the prime historian of John Barrymore and the other hard-drinking upper-Broadway thespians (as they called themselves), came from there; and so did this magazine’s Harold Ross, the epitome of a country boy landing a biplane on Broadway. If there’s any meaning to the pattern, it may be that Colorado wasn’t Iowa. In the tales about the early years of all three guys, there is always an emphasis on con games seen, card games played, a quarrel with Bat Masterson just missed. These guys are not farming. A newspaper-trained poker player coming from Colorado in those years probably thought of himself as cannier and tougher than the city slickers, who were there to be taken. Runyon had met Harry the Horse, or another version of him, before he ever got to town.

And then, just as it takes a naïf to find Paris cafés adorable—the natives find them about as interesting as diners—it took another kind of naïf to think that the lowlifes of Broadway were charming. (Old-timers tell me that the cheesecake at Lindy’s was actually very gummy.) When Runyon at last arrived in New York, in 1910, it took him a while to find his way. He went to work for the Hearst press—not at the Evening Journal but at the American. It’s one of those distinctions that seem slight now but mattered then: the Evening Journal was the popular screaming tabloid, while the American was Hearst’s attempt at a quality paper. So Runyon started out on the higher side of the ledger already, and at the top, covering the New York Giants.

He began his life in New York cautiously; he planted his wife, who followed him from Colorado, in the outer boroughs, and fathered a couple of children in that absent and absent-minded way of newspapermen of the time. Baseball, already the sacrament of the tabloids, was where he made his first mark, and where he seems to have made his first distinct turn: he had come to New York idolizing the great and virtuous Giants pitcher Christy Mathewson, whom he had been writing about back in Colorado for years, sight unseen. Discovering that the real Mathewson was a bit of a prig and a bore—he could play and beat six of his teammates at checkers all at once, but then, Runyon noted, the teammates could barely tell a jump from a julep—Runyon decided to look elsewhere for his stories. He wrote about Bugs Raymond, the drunken, carousing hurler who was Billy Martin to Matty’s Tom Seaver. Runyon pitched his tent on the shady side of the street, where the stories were.

It was only slowly, and over time, that he insinuated himself into the night world that he made his own best subject. His method was a simple form of Broadway Zen: he went to Lindy’s, then an all-night Jewish deli on Broadway, and sat. “I am the sedentary champion of the city,” he explained. “In order to learn anything of importance, I must remain seated. Why I am the best is that I can last an entire day without causing a chair to squeak.” It seems to have been true; the interesting bad guys of that era—the Frank Costellos and Arnold Rothsteins—apparently didn’t mind having newspapermen around who were listening, perhaps because they assumed from first principles that newspapermen were harmless and too intimidated even to need to be bribed.

Basically, Runyon spent the twenties absorbing the material he would use in the thirties. He had published some bad poetry in a Vachel Lindsay manner, and only much later began trying to turn the gangster-talk he heard into stories. But his ambitions were in place all along. This pattern—sportswriter into writer—was so familiar that it is easy to forget its peculiarities. The great American humorists of the first half of the twentieth century divide pretty neatly into newspaper guys and magazine writers, drudges for the penny press and hacks for the slicks, as they thought of themselves. Runyon, Lardner, and Don Marquis were all newspaper writers; Perelman, Thurber, and Benchley all magazine guys. What divided them was education and the felt experience of the Great War. Runyon’s style, like that of Lardner and Fowler and Ben Hecht, is still rooted in prewar expectations. The literary manners of the O. Henry age—particularly the marriage of the louche and the lugubrious—lingers in his work till the end and gives it, along with its energy, a certain stagy quality. So Runyon, though dreaming of “real” writing, dreamed of it in a very late-eighteen-nineties way. [#unhandled_cartoon]

The key moment for Runyon occurred in 1929, after Arnold Rothstein was murdered in a strange, never quite explained hotel shooting. Runyon, as the writer who knew him best, or, at least, was his best listener, felt obliged to produce something, but couldn’t find a way to get it out—until he began to write about the gangsters he had come to know as fictional characters, and, weird stroke of genius, as comic fictional characters. He saw that he could dramatize his accumulated experience of violence on Broadway if he made it funny. He sat down and, in longhand, wrote, “Only a rank sucker will think of taking two peeks at Dave the Dude’s doll, because while Dave may stand for the first peek, figuring it is a mistake, it is a sure thing he will get sored up at the second peek, and Dave the Dude is certainly not a man to have sored up at you.” The story sold to a Hearst magazine for the nice sum of eight hundred dollars. Others followed. Fiction was a way of putting funny hats on hit men.

Stories of this kind, the Runyon story, began to pour out of him for the next decade. Sales figures are hard to find, but it seems fair to say that Runyon became a more genuinely popular writer in the thirties than almost any other American humorist. His stories got sold to Hollywood for twenty films, including “Lady for a Day” (which was later remade, with Bette Davis, as “Pocketful of Miracles”) and “Little Miss Marker,” which made Shirley Temple into a star. Like Anita Loos, he got his first real dose of highbrow appreciation when his stories were published in England, in the mid-thirties.

Reading the thirties stories straight through, one is startled by the lack of characterization. Runyon doesn’t really study gangsters; he just makes up a cookie-shape called Gangster and bakes extras as needed. The lack of sentiment and the love of language are what’s new in his work. Where the other newspaper-made writers tended to be, as newspaper columnists still are, moralistic—Lardner, although a master of common speech, is intent on unmasking the cruelty beneath the cheerfulness of American life—Runyon’s stuff is strictly amoral, with a tearjerking moment set down here and there like last night’s carnation floating by in the gutter. No one grows or changes or learns, everyone’s motive is mercenary, everyone is flat as a pancake, no moral drama takes place—all the life is in the language. Like Wodehouse, whom he in some ways resembles, Runyon inherited a comedy of morals and turned it into a comedy of sounds, language playing for its own sake.

That language still dazzles and delights. The usual thing is to insist that Runyon had an amazing “ear” for natural idiom, but, as Cy Feuer points out, Runyon’s dialogue is essentially unplayable, too far removed from any human idiom to be credible in drama. What Runyon wasn’t doing while he was sitting in Lindy’s was just listening and taking dialogue down. Writers with a good ear (Salinger, John O’Hara) certainly listen more acutely than the rest of us, but what they really have is a better filter for telling signal from noise, and then turning it into song.

There are two layers of idiom-making laid one on top of the other in Runyon’s writing, a technique that accounts both for its complexity and for its comic, slightly out-of-focus nature—for its mixture of authenticity and unreality. As far as one can tell, Jewish crooks of the period really did speak a surprisingly elaborate and cautious diction. They didn’t speak like Runyon characters, but they tried to speak high for the same reason that they polished their shoes and tipped their hats and dressed in suits: fancy was classy. This tendency still shows in Sinatra’s recorded speech, which, when made for public consumption, is extremely “high,” a Hoboken boy’s idea of a class act.

But with Runyon the crucial added thing, as Hamill points out, is that the Narrator is not just telling his stories but writing them. He’s reporting a slang of the streets and writing a yarn at the same time. A whole second story of over-elaboration is placed on top of the already stilted-up vernacular, like one of those buildings on Forty-sixth Street where the ground floor is a restaurant with waiters coming in and out while girls in leotards work out in a dance studio on the floor above. The ever-blossoming additional clauses are most often the Narrator’s idea of written language stapled awkwardly onto his knowledge of spoken language: