You’re killing me, Smalls originates in the 1993 baseball movie The Sandlot. The movie revolves around a boy named Scotty Smalls who moves into new neighborhood and is taken under the wing of the local boys and taught to play baseball.
On two separate occasions in the film, Scotty Smalls displays ignorance about some part of childhood the other boys regard as essential. In the first case, the character Ham Porter asks him if he wants a s’more. Misunderstanding the question, Smalls asks, “S’more what?” After a bit of back-and-forth, Ham exclaims in exasperation, “You’re killing me, Smalls” and explains what a s’more is. Ham uses the phrase again when Smalls, after he’s offered chewing tobacco, asks, “What do you do with it?” much to the irritation of his friends. The popularity of both the character Ham and the feel-good, coming-of-age film itself helped cement the line in pop culture.
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