An organ grinder plays his hand-cranked organ outside a theater advertising a "Season of Grand Opera." On the sidewalk in front of him is his monkey, dressed in a red suit and holding a tin cup. Organ grinders, mainly Italian immigrants, were street entertainers who played songs on hand-cranked organs.

Arthur Weindorf was a listed illustration artist based in New York City. Born and raised in Queens, he drew for many local newspapers and magazines there. Early in his career, he was a political cartoonist for the Long Island Daily Star (see example here). From 1908 to 1944 he worked for the New York City subway system, drawing and developing maps, models, architectural designs and other materials. He was also known for his genre and figure paintings, which he exhibited nationally. His work frequently exhibited a playful sense of humor. Weindorf was a member of the Society of Independent Artists, where he exhibited regularly from 1920-43. After his death in 1979, the borough president of Queens issued a proclamation in his honor for his services to the borough and the city's subway system, and "his efforts to promote a greater understanding and appreciation of the history of Queens."

Reference:

"Proclamation [in honor of Arthur Weindorf]." Borough of Queens, City of New York. 25 May 1979.