A whimsical and satirical yet deftly rendered original self portrait watercolor painting dated 1948 by the legendary American illustrator and New York City resident James Montgomery Flagg. The artist paints himself tiptoeing along the roofline of a posh Park Avenue neighborhood in the guise of a snarky Psychiatrist with a Central Park night time cityscape under a full moon as the backdrop. In an homage to the classic German Expressionist silent film horror, “The Cabinet of Dr. Caligari,” he takes on the role of the crazed somnambulist Cesare (Conrad Veidt) as he deliriously skips atop wall ledges in the middle of the night. A playful look at the duality of human nature. Hearkening back to the film, Flagg’s joke appears to be that the psychiatrist, though he spends every day getting his clients to face their inner demons, maintains a secret shadow life as a randy tomcat. Hand painted gag line reads “Private Night Life Of A Park Avenue Psychiatrist – Dick Hoffman Sings – I Wonder Why I’m On the Tiles When Pussycat Sleeps In Bed And Smiles.” Dick Hoffman was indeed a prestigious analyst in NYC at the time, and a local celebrity. He appeared as one of the panelists on the first telecast of “What’s My Line,” and at the time this artwork was created, the Hoffman family was in the news for a highly public affair his son was carrying on with an heiress to the Dodge motor empire. The genuine affection between Flagg and his gadfly friend are apparent in this charming watercolor. Even in this quick working the cleverness and technical precision of Flagg is on display. Painting is framed behind glass in the original simple wood frame with original matting.