I have always loved 1920s gangster speak! Actually, aside from the slang that pertains to crime, it really emanated from a mostly urban youth culture in the decade of the 1920s that reminded me of my own youth in the 60s. In both eras if you wanted to belong to hip current trends it was incumbent upon you to communicate properly, and I highly doubt that much has changed in that respect about being "hip."
Over the last four decades as I worked on my book, Deadly Valentines [Chicago Review Press, $24.95], researching the Capone era, the real gems that I found were always what Jack McGurn or his paramour, Louise Rolfe, actually said. Their idiom was almost perfectly pure because until 1927 there were no talking films. After The Jazz Singer, colloquial speech was no longer in the screen titles; you could hear the voice and all the nuances that accompanied it. The first cinematic criminal roles copied the gangsters in New York and especially Chicago. Edward G. Robinson and James Cagney studied the Capone boys and how to sound like them, and so did the scriptwriters. Jack McGurn and Louise Rolfe did most of their talking to newspaper reporters after the Saint Valentine's Day Massacre in 1929. The early talkies scriptwriters eagerly emulated them, picking up their authenticity for the movies. Robinson even attended the tax evasion trial of Al Capone in October, 1931, sitting at the back of the courtroom taking notes.
In the 1920s, gangsters like Jack McGurn - Al Capone's main assassin and general of his troops - would begin many sentences with "Say." For example: "Say, what's the beef?" Or, "Say, I wasn't anywhere near the place. See?" Say and see were like bookends to the street comment. I find it interesting that there is so often a hip way of commonly beginning a sentence and every generation has their own. But the deeper gangster speak requires knowledge of a lexicon that is pure street poetry.
For example, Al Capone might say: "Jack, go uptown with Roscoe and send this punk's mother some flowers. See?" And Jack would reply: "Sure!" Translation: "Jack, drive into the city and kill this guy. Understand?" Jack: "I read you loud and clear!"
The subcultures of the '20s were stuffed with great hipster colloquialisms. Gams were women's legs. Pretty women were Dolls; Pretty women like Jack McGurn's girlfriend, Louise Rolfe, were Molls because they hung out with gangsters. Guns were rods, Roscoes, or gats. Somebody who shot at you was "throwing lead." If you were killed, you were "bumped off," "rubbed out" or "taken for a ride." If you went to prison you were "away at college" or "on vacation." If you were inebriated you were "spifflicated," "boiled as an owl" or "blotto." A gal who was "hot" was "running wild," a "flaming youth" and she had "animal magnetism." If you were ambushed you were "put on the spot."
Quite often ordinary people living outside large cities found it difficult to even understand the hipster-talking urban denizens until films and radio began to illuminate the meaning. Soon everybody was incorporating various terms into their own speech because if you think film is a powerful medium now, it was a cathartic genesis in the late '20s and early '30s.
So the hipster speak went from the young people on the streets to the hinterlands via print, radio, and especially movies. Here's a little paragraph from Chicago in the '20s:
"Say, what's coming off? You had the heebie jeebies last night, see? I thought you were gonna' snap your braces! One minute you were taking a gander at that oater, and before I knew it you were on the lam, your peepers were pie tins! Then you went scorching!"
Want to offer up a translation?