As the first musicological study on the 1940 painting Sentimental Ballad by the American artist Grant Wood, this article relates said image and its creation to the American history of song and the popular. The painting’s depiction of a group of male sailors who sing and weep over their alcoholic drinks is traced back not only to its Hollywood background, a scene from the movie The Long Voyage Home (directed by John Ford), but also to the cycle of plays by Eugene O’Neill on which the film is based and to the Tin Pan Alley song “When Irish Eyes Are Smiling” by Chauncey Olcott, George Graff Jr. and Ernest R. Ball. From a Situational Analysis perspective, the article examines Grant’s painting in relation to contemporary concepts of high/low-hierarchies and popularity, to nostalgia for Irishness in popular culture as well as to processes of negotiating the relation of masculinity and sentimentality.