He was best known for his short stories celebrating the world of Broadway in New York City that grew out of the Prohibition era. He spun humorous tales of gamblers, hustlers, actors, and gangsters; few of whom go by "square" names, preferring instead to be known as "Nathan Detroit," "Big Jule," "Harry the Horse," "Good Time Charley," "Dave the Dude," "The Seldom Seen Kid" and so on. These stories were written in a very distinctive vernacular style: a mixture of formal speech and colorful slang, almost always in present tense, and always devoid of contractions.
Here is an example from the story Tobias the Terrible, collected in More than Somewhat (1937):
If I have all the tears that are shed on Broadway by guys in love, I will have enough salt water to start an opposition ocean to the Atlantic and Pacific, with enough left over to run the Great Salt Lake out of business. But I wish to say I never shed any of these tears personally, because I am never in love, and furthermore, barring a bad break, I never expect to be in love, for the way I look at it love is strictly the old phedinkus, and I tell the little guy as much.
To New Yorkers of his generation, a "Damon Runyon character" evoked a distinctive social type from the Brooklyn or Midtown demi-monde. The adjective "Runyonesque" refers to this type of character as well as to the type of situations and dialog that Runyon depicted.
Runyon was also a newspaperman. He wrote the lead article for United Press on Franklin Delano Roosevelt's inauguration in 1933.
After a notable failure in trying to organize a Colorado minor baseball league, Runyon moved to New York City in 1910. For the next ten years he covered the New York Giants and professional boxing for the New York American. In his first New York byline, the American editor dropped the "Alfred," and the name "Damon Runyon" appeared for the first time.
A heavy drinker as a young man, he seems to have quit the bottle soon after arriving in New York, after his drinking nearly cost him the courtship of the woman who became his first wife, Ellen Egan. He remained a heavy smoker.
His best friend was mobster accountant Otto Berman, and he incorporated Berman into several of his stories under the alias "Regret, the horse player." When Berman was killed in a hit on Berman's boss, Dutch Schultz, Runyon quickly assumed the role of damage control for his deceased friend, correcting erroneous press releases (including one that stated Berman was one of Schultz's gunmen, to which Runyon replied, "Otto would have been as effective a bodyguard as a two-year-old.")
Runyon frequently contributed sports poems to the American on boxing and baseball themes, and also wrote numerous short stories and essays. He was the Hearst newspapers' baseball columnist for many years, beginning in 1911, and his knack for spotting the eccentric and the unusual, on the field or in the stands, is credited with revolutionising the way baseball was covered. Perhaps as confirmation, Runyon was inducted into the writers' wing (the J. G. Taylor Spink Award) of the Baseball Hall of Fame in 1967. He is also a member of the International Boxing Hall Of Fame and is known for dubbing heavyweight champion James J. Braddock, the "Cinderella Man."
Gambling was a common theme of Runyon's works, and he was a notorious gambler himself. A well-known saying of his paraphrases Ecclesiastes: "The race is not always to the swift, nor the battle to the strong, but that's the way to bet."
Runyon's marriage to Ellen Egan produced two children (Mary and Damon, Jr.), and broke up in 1928 over rumors that Runyon had become infatuated with a Mexican girl he had first met while covering the Pancho Villa raids in 1916 and discovered once again in New York, when she called the American seeking him out. Runyon had promised her in Mexico that, if she would complete the education he paid for her, he would find her a dancing job in New York. Her name was Patrice Amati del Grande, and she became his companion after he separated from his wife. After Ellen Runyon died of the effects of her own drinking problems, Runyon and Patrice married. Though Runyon forged a better relationship with his children, the marriage ended when Patrice left him for a younger man in the same year he died (1946).
The Damon Runyon Cancer Research Foundation, established in his honor, was set up to fund promising scientists in the field of cancer research.
Every year, the Denver Press Club hands out the Damon Runyon award to a notable journalist.
The near total avoidance of past tense (it is used only once, in the short story "The Lily of St Pierre") is not the only oddity of Runyon's use of tense; he also avoided the conditional, using instead the future indicative in situations that would normally require conditional. An example: "Now most any doll on Broadway will be very glad indeed to have Handsome Jack Madigan give her a tumble ..." (Guys and dolls, "Social error"). There is an homage to Runyon that makes use of this peculiarity ("Chronic Offender" by Spider Robinson) which involves a time machine.
Some examples of Runyonesque slang terms include the following:
There are many recurring composite phrases such as:
Runyon's stories also employ occasional rhyming slang, similar to the cockney variety but native to New York (e.g.: "Miss Missouri Martin makes the following crack one night to her: ‘Well, I do not see any Simple Simon on your lean and linger.’ This is Miss Missouri Martin’s way of saying she sees no diamond on Miss Billy Perry’s finger.” (from "Romance in the Roaring Forties").
The comic effect of his style results partly from the juxtaposition of broad slang with mock-pomposity. Women, when not "dolls" (or "Judies", "pancakes", "tomatoes", "broads" etc.), may be "characters of a female nature".