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Held was the premier illustrator and cartoonist of the jazz age. When he was just fifteen, Held sold a work of his art to Life magazine. He continued creating illustrations for magazines including Vanity Fair and The New Yorker. Held developed his characteristic style by 1920, which pictured stiff, stylized figures prior to their symbolic definition of the decade. His magazine covers offered humor for dismayed traditionalists, and style models for the younger flappers with shorter skirts and pencil-like necks. Held was incredibly successful, earning over one million dollars a year at one point and owning a private zoo and golf course. This drawing shows three figures, a couple seated on a couch and an older man reading a book. The couple on the couch are going on a date or to a dance, wearing corsages. They sit far away from each other, perhaps communicating shyness or even dissatisfaction with one another or with the night. The male folds his arms as he peeks over to the left, while the female looks down towards her side, with hands folded.