Grosz's Germany: A Winter's Tale was painted from 1917 to 1919. (The title was taken from the poet Heinrich Heine, "Deutschland. Ein Wintermarchen".) It is widely considered one of the seminal works in 20th-century socio-critical art. In the middle of the picture, surrounded by the familiar turmoil of city chaos, sits a rotund philistine clutching his knife and fork, gaping with bewilderment. Before him is a plateful of gnawed bones and a bottle of beer with the Iron Cross on the label. These, and his cigar and newspaper, satisfy the good citizen's needs. Below we see the triumvirate that underwrite his society: the priest, the general and the teacher, the last puffy-cheeked and bulbous-nosed, double-chinned and thick-necked, cane in hand and a volume of  Goethe held to his breast. Grosz returned to the subject of this lower part of the painting in his 1926 Pillars of Society. At the bottom left, an adumbrated profile of the artist appears in silhouette, jaw out-thrust in fury.

Count Harry Kessler, a diplomat and patron of the arts of whom Grosz wrote in his autobiography that he was perhaps the last true gentleman, left a diary with a vivid account of the period. On 5 February 1919, Kessler recorded his impressions of the painting and of Grosz: "This morning visited the painter George Grosz in Wilmersdorf (Nassauische Strasse 4). Wieland and Hellmuth Herzfelde there. Grosz had a big political painting, Germany: A Winter's Tale, poking fun at the ruling classes, the pillars of the well-fed indolent bourgeoisie (bolster). He said he would like to be the German Hogarth, deliberately concrete and moral; to preach, ameliorate, reform. [...] Then Grosz said that art as a whole was unnatural anyway, an illness; the artist was obsessed, a man possessed of a mania. The world did not need art, he said; people could get by without art." Kessler describes Grosz a Bolshevik of art, nauseated by painting, concluding: "In fact his thinking is in part rudimentary, in terms of its intellectual substance, and easy to contest."