The Delicate Delinquent (1957)

Jerry Lewis' first solo effort was also his first headlong plunge into pathos. The Delicate Delinquent stars Jerry as mixed-up teenaged janitor Sidney Pythias, a nice kid on the verge of throwing in with a not-so-nice street gang. Sensing potential in Sidney, police officer Mike Damon (Darren McGavin, in role originally intended for Lewis' ex-partner Dean Martin) takes the boy under his wing. To prove that Sidney can be weaned away from bad influences, Mike arranges for the boy to become a rookie cop, with fitfully hilarious results (the best scene, involving a monolingual Japanese gentleman, is also the most politically incorrect). Martha Hyer costars as an idealistic social worker with whom Mike (and briefly, Sidney) falls in love. The film's tenuous balance between juvenile-delinquent drama and slapstick comedy is never more pronounced than in the opening scene, wherein the clumsy Sidney, carrying a bulky garbage can, stumbles into the middle of a gang rumble. Though not Jerry Lewis' best film, Delicate Delinquent was a hit, proving he could carry a picture himself; as a bonus, Jerry gets to sing the significantly titled ditty "By Myself".