This moving portrait of an older man was made in northern Italy, probably in the 1490s. The man’s pensive gaze suggests an introspective mood. His unshaven chin, wrinkled flesh, sunken cheeks and eyes, and thinning hair are rendered attentively, with uncompromising naturalism—evidence of the artist’s earnest inquiry into the aging process. The skillful application of charcoal—which ranges from bold, velvety lines to very light hatches, blended with a stump and brush—creates a convincing impression of plasticity and volume.