Painted portraits on wood and cloth were common in the ancient world and prized as authentic and lifelike images. Affordable, portable, and desirable, they were an important form of representation, but rarely survive in the archaeological record outside Egypt. This article approaches the study of painted portraiture in a way that does not necessitate the survival of the images themselves. It analyzes evidence for the use, reuse, and imitation of painted portraits in the catacombs of 4th-c. Rome by examining the remains of settings and attachments for portraits, the shadows left by them on walls, and portraits in other media which imitate panel paintings. The article considers why painted portraits were so effective in funerary contexts and what connection they may have had to domestic portraiture. It also explores the development of panel portrait imitation through the phenomenon of the “square nimbus.”