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In Baltimore in 1953, "Cry-Baby" Wade Walker is the leader of a gang of "Drapes". His ability to shed a tear, symbolized by the teardrop tattoo on his face, drives all the girls wild. One day after school, he is approached by Allison Vernon-Williams, a pretty girl tired of being a "Square", and the two fall in love.

Despite Allison's grandmother being skeptical, Allison stays and sings with the Drapes. Allison's jealous square boyfriend Baldwin starts a riot at the local Drape hangout, Turkey Point. Cry-Baby is blamed for the fighting and sent to a penitentiary, outraging all his friends and even Allison's grandmother, who is impressed by Cry-Baby's posture, manners and musical talent.

As Lenora, a girl with a crush on Cry-Baby but constantly rejected by him, claims to be pregnant with his child, Allison feels betrayed and returns to Baldwin and the Squares, though her grandmother advises against rushing into a decision. Eventually, she is persuaded by the newly-established alliance between the drapes and her grandmother to stand by Cry-Baby and join the campaign for his release. Cry-Baby is released but immediatedly insulted by Baldwin, who challenges him to a chicken race. Cry-Baby wins ,as Baldwin chickens out, and is reunited with Allison.

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