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The 1523 Longford Castle portrait of Erasmus is in some ways Hans Holbein the Younger’s sequel to the Praise of Folly. In the portrait, both men are implicated in the problem of satire, and of cultural production as a critical format in general: can one match one’s models and objects of critique, or does one too easily devolve into mere mockery? The panel is a playground in which both men confront their relation to specific models, but also more generally to antiquity and to their respective traditions of painting and scholarship. In this context, this paper will playfully relate the panel to Erasmus’s later complex engagements with religious schism, Ottoman military encroachment, and Holbein himself. Finally, if the distinction between mockery and imitation emerges as a core topos of representation, how can humor suggest anything but failure?