This fall, photographer Bruce Weber’s new show, “My Education,” at the Prague City Gallery, will reveal 300 images taken over five decades.

One image in particular stands out—a portrait of the Spanish film director Pedro Almodóvar staring straight at the camera with an almost cartoonish cat sitting on his great thatch of hair. The broad-faced duo wear similar expressions of round-eyed curiosity. At once intimate and playful, it is vintage Weber.