Visual examples of the Tudor and Stuart grotesque (properly called 'antique-work') regularly feature a motif known as the 'naked boy'. Much English Renaissance antique-work remains as yet unsurveyed in scholarship and the naked boy has attracted very little attention. This article maps the Tudor-Stuart interrelationship of antique-work and naked boys, with particular focus upon the relevant work by Hans Holbein, Franz Cleyn, and Inigo Jones. The naked boy plays with imitative civility or Bacchic revelry in a reorganized cosmos of the grotesque. He signifies a wide range of early modern concerns, from humanist wit to artistic invention, philosophical scepticism to political ideology, and Bacchic Neoplatonism to Christian meditation.