The complicated relationship between American and European cultural production, particularly in the nineteenth century, is the subject of this chapter. American essayists of this period were, on the one hand, greatly influenced by the literature and culture of Europe and sought to absorb its lessons into their own writing. On the other, these same essayists pushed back against the idea that European writing should be their primary influence. Instead, they frequently critiqued Europe from afar and sought to develop a new idiom and fresh form of expression unique to the United States. Writers like Washington Irving, Walt Whitman, Ralph Waldo Emerson, Margaret Fuller, Edgar Allan Poe, Frederick Douglass, Henry James, and Henry David Thoreau explored the many tensions between the United States and Europe in their essays and used them to debate the extent to which America should remain in Europe’s cultural shadow.