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When one looks back through history, it would seem that ideals of American manhood have changed since America was founded. Competing ideas of what a man should be abound in literature, causing an obvious question to arise: what does American literature say the ideal man should be? I’ve found that the codes of conduct for men in the earliest works of American literature, such as John Winthrop’s sermon “A Model of Christian Charity” and John Smith’s A Letter to New England are not represented in the conduct of men in later works of American literature. The writings of Washington Irving provide us with a picture of a transitional state in the American ideals of manhood. Analysis of Irving’s “The Legend of Sleepy Hollow” and “Rip Van Winkle” shows that America’s independence from Britain also precipitated a shift in literary ideals of manhood.