ARGANTE and GERONTE, two competing Chicago mob bosses, are away on secret business. Their respective sons OTTO and LEO (secret long-time pals) meet at the LAVENDER GYPSY speakeasy, a drag-bar, because "no one would ever figure us for coming to this kind of place." There, despite the vigilance of their respective bodyguards SYLVESTER and PINKY, the two young men are smitten with love, Otto with HYMENA, a lost and penniless girl who speaks no English, and Leo (shockingly to him) with a transvestite singer named ZORA. The youngsters impulsively marry only to then be immediately separated; Hymena by her malaprop-spouting spinster chaperone EPINEPHRINE, and Zora by the LAVENDER GYPSY GANG to whom Zora is deeply in debt. Distraught, the two young men fall out as they search desperately for ways to get back their respective loves.
Word arrives that the fathers have returned with plans that Otto marry Geronte's secret and hitherto unknown daughter, a move that will cement the bonds between the two mobs and present a united front against incursions into their territory by the Capone crime syndicate. Otto is terrified of his father finding out that he has gotten married and fouled up the Argante-Geronte deal.
He crosses paths with ARLO KEENO, a two-bit conman who's being run out of town by Geronte. In return for being saved from Geronte's men, Keeno persuades first Otto, then Leo, that he will assist them in dealing with their fathers. His efforts to help only scramble the situation into a worse mess, with Argante threatening to disinherit Otto for fouling up his plans, and Geronte threatening to disinherit Leo if he discovers Leo's been engaged in "dishonorable behavior", leaving Leo in a panic over his love for a transvestite and in a rage against Keeno for possibly spilling the beans.
Meantime, Keeno sets a devious plot in motion, not only persuading the fathers that they really want what they don't want and don't want what they do want, but also conning them out of money on behalf of the young lovers and himself. As well, he takes out a furiously comic revenge on Geronte for having tried to run him out of town. In a dizzying series of events filled with disguises and imaginary hitmen, fathers find long-lost children, young lovers are reunited, and even Keeno is forgiven his trespasses.
All ends happily with Keeno telling everyone "Life is short, so dance 'til you drop."