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Featuring the image of an athlete tugging at a rooted sapling, Impossible is the most enigmatic of the many small-scale engravings produced by Hans Sebald Beham. Juxtaposed with the adage “Nobody should dare great things that are impossible for him to do,” the image not only challenges the astute viewer to a game of wits: the resulting paradox also unleashes a cascade of ethical questions concerning the boundedness of the will, Christian freedom, human perfectibility, and the paradoxical conditions of self-knowledge. These issues came to the fore in the sixteenth-century debate over free will, which pitted humanists, magisterial, and radical reformers against one another. Beham's documented experience as a religious and political dissident during the 1520s raises the possibility that the print, made later in life, embeds still another allegorical layer: the conflicted situation of the artist in an era of reform and iconoclasm, Renaissance and revolution, hope and disillusionment.