A friend or a studio assistant may have posed for this intimate portraitlike study drawn from life, probably in the 1520s, when Pontormo, having emerged as a revolutionary proponent of Mannerism in Florence, was at work on the most significant paintings of his maturity: cycles for the Medici villa in Poggio a Caiano, the Certosa del Galluzzo (near Florence), and the Capponi Chapel at the Church of Santa Felìcita. As in many of the studies prepared for these projects, the artist here captured a fleeting psychological moment in the turn of the man's head, his penetrating sunken gaze, and the dimpled tightening of his lips. Pontormo's mastery as a figural draftsman was largely the product of ceaseless drawing, especially in red chalk, before a live model. This newly identified sheet displays an arresting command of the artist's favorite medium. Passages of broad parallel hatching alternate with areas of seamless stumping in the shadows, while the curls of the man's hair and beard are sketched quickly with curved strokes. Pontormo accented the darkest shadows by wetting the tip of his chalk stick, which was pressed deeply into the paper, and created intense highlights by leaving the paper starkly in reserve in small areas.