For Guys and Dolls who follow Such Matters, A Vocabulary of the ‘20’s and ‘30’s Slang Used in this Story

(Many of these meanings are specific to the U.S. underworld during this period, or to prison, or even to particular New York state prisons.)

Ace-deuce—one’s best friend. Still in use, although sometimes spelled and pronounced ace-duce.
Ashes hauled—to obtain sex.
Attitude Case—a difficult, violent, or insolent prisoner, as judged by the prison guards and administration.
Back Room parole—died in prison.
Boss—a supposedly respectful term for guard. It actually originates from an abbreviated reversal of sorry-S.O.B..
Box—a prison cell. Also, a coffin.
Broadway—the bottom floor of the block. Wider, because there is a lot of traffic through it.
Bullpen—prison.
Can—the toilet
Chew the rag—to gossip, to chatter.
Chow hound—a glutton.
Court—a small section of a prison yard, the territory of a group of men. Also, the men of a particular court.
Cut Loose—to release.
Cutter—a revolver.
Dating—appointments for social or sexual purposes.
Dock rats—vagrants and minor criminals who loiter around the docks.
Epicurean—a type of philosophy that insists that the good life involves sitting around in your own house, eating intelligently, drinking a little, reading, and chatting with your friends. This was held to be horribly immoral by the Stoics and Neoplatonists.
Fade—to depart, to escape.
Family man—to have children, but also to be a criminal or associated with organized crime.
Fat chance—no chance.
Fish—a new prisoner.
Fist—a five year sentence.
Fixer—one who arranges deals, usually under the table. A go-between.
Fried—executed in the electric chair.
Gear—a homosexual, usually passive.
Gull—a fool, a victim of a con.
Hard-Timer—a prisoner serving a long prison sentence, usually in maximum security.
Heavyweight—a criminal prone to using violence.
Heeled—to be armed
Hole—a punishment cell.
Hooch—cheap, bootleg alcohol.
Hoosier—a new, naïve prisoner.
Hot nuts—strong (male) sexual desires.
Iron House—a prison.
Jack off—to masturbate.
Jawing—to converse.
Kitten—a young, inexperienced woman.
Lags—prisoners.
Laughing Boy—someone taunted for a fast, possibly excessive, slide into misery. From a G&S operetta.
Leaky—to be tearful or weepy.
Lifer—a prisoner serving a life sentence.
Line up on—to gang-sodomize.
Mill—a prison, sometimes one dedicated to transient prisoners.
Mouthpiece—an attorney
Mug—a thug, especially a stupid one.
Outside—out of prison.
Over the Wall—to escape from prison.
Pearl Diver—a dishwasher.
Pen—a prison.
Piece—a gun. Also, a penis.
Pretty—a young, inexperienced homosexual.
Protection block—cells set aside for prisoners who must be protected from the general prison population.
Prune-juice—moonshine distilled from prunes and/or raisins.
Punk—a young inmate used for sex by older prisoners.
Screws—the prison guards.
Seneca—a Roman stoic philosopher. IMO, those who kiss up to members of the Roman imperial family shouldn’t be surprised when they are first exiled and then forced to commit suicide, and shouldn’t write long screeds blaming it on fate, either.
Sharp—to be fashionable, good, admirable.
Shiv—a knife, in prison often home-made from metal.
Short—to be close to the end of a prison term.
Sidewinder—a bodyguard, a sidekick.
Smart-ass—Archie Goodwin.
Spill—a small piece of paper that holds something, usually a powder, often a drug. Also, a small drink.
Spring a leak—to urinate.
Spunk—semen.
Stash—money, supplies, a hiding place.
Stick—a truncheon. Also, a penis. Also, to stab.
Strong-arm man—a thug, a gangster.
Tie to—to trust.
Tier—a floor of a cell block.
Tip—a prison gang.
Tongue bath—to have one’s entire body, including the genital and posterior regions, systematically licked and sucked. My secondary sources date this term to the 1960’s, but I, myself, have seen it in a primary source from the twenties.
Torch job—to commit arson.
Walk tall—to behave boldly and aggressively.
Wise—to be shrewd, stupid, or in the know, depending upon context.
Wolf—in prison, any violently predatory man seeking homosexual sex. Out of prison, an older, paternal homosexual, or the penetrating partner in anal sex.
Wore long pants—traditionally, a boy was taken out of shorts and put into long pants to mark the onset of pre-adolescence.
Yard—a large, open prison exercise area.