Eckhard Hess's claim that pupils dilate to pleasant images and constdct to unpleasant images was confounded because of inconsistent contrasts and luminances across his images. Building upon the work of Powell and Schirillo (2011) that explored multiple portraits by Rembrandt, we offer a new and promising methodology that overcomes this limitation. We presented leftward-or dghtward-facing female and male portraits by 12 artists from various epochs to observers in either their odginal or mirror-reversed positions. Simultaneously, we asked observers to report how (dis)pleasing they found each image while measudng their pupil size. We found that pupil diameter was a function of arousal only while viewing male portraits. That is, for male images rated both low and high in pleasantness, larger pupil diameters were obtained. We postulate that our findings may be the result of the perceived dominance of males and how hemisphedc laterality may ddve emotional expression.