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High modernist poetry, particularly Gertrude Stein’s 1923 poem “If I Told Him: A Completed Portrait of Picasso,” is often considered impenetrable and distinct from Stein’s more clearly humorous prose work. However, the poem invites us to laugh at the chaos of our world through the chaos and instability of language. This article explores the poem’s humor and the possibilities for pleasure it offers through the rhythm of repetition. Stein’s playfulness points to an oft-overlooked aspect of high modernism: its appeal to our most visceral selves.