While convalescing in Frankfurt after a mental breakdown during World War I, Max Beckmann befriended Lili von Braunbehrens, the twenty-year-old daughter of an army official who helped smooth his release from the military. Braunbehrens, who was nearly blind, recorded her impressions of her nightly wanderings through Frankfurt in twenty poems that Munich-based Reinhard Piper, at Beckmann's urging, published as Stadtnacht (City night). Beckmann illustrated six poems and the title page.

The collection opens with a glimpse of a gruesome murder, witnessed through the window of a cheap apartment building. In the modern metropolis there is no refuge, not even at home. One print shows the revelries of a group of nouveaux riche seemingly oblivious to the surrounding economic and social collapse, while a brothel scene commodifies human interaction. The rest depict the hopelessness of working-class life. In most of the prints, figures spill out of the cramped and distorted spaces, heightening the feelings of alienation and loneliness.

In his illustration of the poem "Verbitterung" (Bitterness), Beckmann showed himself looking through an apartment window to the streets below, isolated from human contact. In the final print, Die Kranke (The sick one), he depicted an emaciated figure in a sparsely furnished room facing the end alone. Throughout Stadtnacht, Beckmann used Expressionist techniques of distortion and exaggeration to underscore the failures of postwar society.