This dissertation explores the relationship between pictures and the lighting conditions in which they were originally viewed. Using advanced rendering technology, I reconstruct the original architectural context in which a work of art was displayed and simulate the effects of variable daylight and artificial illumination on the picture's appearance. This research methodology enables me to describe the interaction between real lighting and depicted lighting relative to the picture's symbolic content. I provide a typology of these interactions (which I call "pictorialized illumination") using examples from diverse art historical traditions. In the final chapters, I analyze two case studies: Leonardo da Vinci's Last Supper at the refectory of Santa Maria delle Grazie in Milan, and Peter Paul Rubens's altarpiece for the church of Santa Maria in Vallicella in Rome.