Motion can be perceived in static images, such as photos and figurative paintings, representing realistic subjects in motion, with or without directional information (e.g., motion blur or speed lines). Motion impression can be achieved even in non-realistic static images such as motion illusions and abstract paintings. It has been shown that visual motion processing affects the diameter of the pupil, responding differently to real, illusory, and implied motion in photographs (IM). It has been suggested that these different effects might be due to top-down modulations from different cortical areas underlying their processing. It is worthwhile to investigate pupillary response to figurative paintings, since they require an even higher level of interpretation than photos representing the same kind of subjects, given the complexity of cognitive processes involved in the aesthetic experience. Also, pupil responses to abstract paintings allows to study the effect of IM perception in representations devoid of real-life motion cues. We measured pupil responses to IM in figurative and abstract artworks depicting static and dynamic scenes, as rated by a large group of individuals not participating in the following experiment. Since the pupillary response is modulated by the subjective image interpretation, a motion rating test has been used to correct individual pupil data according to whether participants actually perceived the presence of motion in the paintings. Pupil responses to movies showing figurative and abstract subjects, and to motion illusions were also measured, to compare real and illusory motion with painted IM. Movies, both figurative and abstract, elicit the largest pupillary dilation of all static stimuli, whereas motion illusions cause the smallest pupil size, as previously shown. Interestingly, pupil responses to IM depend on the paintings' style. Figurative paintings depicting moving subjects cause more dilation than those representing static figures, and pupil size increases with the strength of IM, as already found with realistic photos. The opposite effect is obtained with abstract artworks. Abstract paintings depicting motion produce less dilation than those depicting stillness. In any case, these results reflect the individual subjective perception of dynamism, as the very same paintings can induce opposite responses in observer which interpreted it as static or dynamic. Overall, our data show that pupil size depends on high-level interpretation of motion in paintings, even when they do not represent real-world scenes. Our findings further suggest that the pupil is modulated by multiple top-down cortical mechanisms, involving the processing of motion, attention, memory, imagination, and other cognitive functions necessary for enjoying a complete aesthetic experience.