Jack Clifford, born Virgil James Montani, was originally from Geneo, Italy. Clifford’s vaudeville fame came from his live performances, both as an actor and dancer. Clifford was noted for his marriage to Evelyn Nesbit in 1916, and after a fifteen year separation ended in divorce in 1933. Clifford died on November 10, 1956, at the age of 76, in New York. In this portrait Clifford is captured in a relaxed atmosphere, seated with an opened newspaper on his lap. Clifford is attired in casual clothing, a white shirt, a black ribbon bow tie, suit vest and pinstripe pants. A few whimsical props accentuate Clifford's overall appearance, a corn cob pipe and two sets of spectacles. The eye glasses are curiously positioned as one pair is properly placed on the bride of his nose while the secondary set rests absentmindedly on his head. Clifford's gaze is directed slightly to the right, as he positions his left hand behind his right ear, in an attempt to amplify his hearing. The wooden chair, in which Clifford sits, appears care worn with slight scuffing on the arm of the furniture. The background is very dark, which accentuates the central figure.