This is the second of two portraits George Grosz painted of his friend, writer Max Herrmann-Neisse. After countless hours in Grosz's studio, which yielded more than thirty preparatory drawings for the portraits, Herrmann-Neisse said he felt "completely at home" there. In this portrait, Herrmann-Neisse slumps deeply into a chair, lost in thought. Grosz meticulously yet sympathetically presents Herrmann-Neisse and his distinctive features, such as his hunchback and oversize bald head. The artist details the lines, bumps, veins, gnarls, and ruddiness of his friend's head and hands, placing him almost within arm's reach.

Grosz and Herrmann-Neisse shared the same politics, sense of humor, and cynical outlook. They were, as Herrmann-Neisse later recalled, both "proper and anarchistic." Herrmann-Neisse, Berlin's leading cabaret critic, guided the way in their nocturnal adventures. Together they dove into the seediest nightspots, while also moving in the same intellectual circles and contributing to the same periodicals.