Hollow Men analyzes texts and art objects from the late 14th to the late 16th centuries to show that Renaissance theories of emulating classical heroes generated a deep skepticism about representation, as these theories forced men to construct a public image that seemed fixed but could adapt to changing circumstances. The book shows that writers and their patrons appropriated objects to create a public image that would be both fixed and adaptable: a paradox deriving from ideals of exemplary imitation, which taught that an educated man must emulate the ancients to present a coherent identity and be memorialized as an example for future generations. Yet Italian intellectuals were increasingly cut off from political power; their classical models (both texts and objects) were broken and unreadable; and men had to adapt to changing political circumstances while avoiding the suspicion of “feminine” changeability. There emerged a growing distrust surrounding claims for the equivalence between exemplary external image and inner state, as self-presentation increasingly resembled deception. Chronologically-arranged analyses show that the Renaissance questioning of “interiority” derived from a visual ideal, the monument that was the basis of teachings about imitation; and that this questioning contributed to a new awareness of representation as representation. Hollow Men also demonstrates that the decline of exemplary pedagogy and the emergence of modern masculine subjectivity were well under way in the mid-15th century (much earlier than their typical 16th-century dating); and that these changes were hastened by the rapid development of the printed image, over the following century.