Several papers by Eckhard Hess from the 1960s and 1970s report that the pupils dilate or constrict according to the interest value, arousing content, or mental demands of visual stimuli. However, Hess mostly used small sample sizes and undocumented luminance control. In a first experiment (N = 182) and a second preregistered experiment (N = 147), we replicated five studies of Hess using modern equipment. Our experiments (1) did not support the hypothesis of gender differences in pupil diameter change with respect to baseline (PC) when viewing stimuli of different interest value, (2) showed that solving more difficult multiplications yields a larger PC in the seconds before providing an answer and a larger maximum PC, but a smaller PC at a fixed time after the onset of the multiplication, (3) did not support the hypothesis that participants’ PC mimics the pupil diameter in a pair of schematic eyes but not in single-eyed or three-eyed stimuli, (4) did not support the hypothesis of gender differences in PC when watching a video of a male trying to escape a mob, and (5) supported the hypothesis that arousing words yield a higher PC than non-arousing words. Although we did not observe consistent gender differences in PC, supplementary analyses showed gender differences in eye movements towards erogenous zones. Furthermore, PC strongly correlated with the luminance of the locations where participants looked. Overall, our replications confirm Hess’s findings that pupils dilate in response to mental demands and stimuli of an arousing nature. Hess’s hypotheses regarding pupil mimicry and gender differences in pupil dilation did not replicate.