Bill veterans, including Leon Golub, Cosmo Campoli and H. C. Westermann, who would join Don Baum, Dominick Di Meo, June Leaf, and Nancy Spero to form the influential movement later dubbed the "Monster Roster" by critic Franz Schulze, which was a precursor to the more well-known Chicago Imagists.

[3][4][5][6] Like others in the group, Rosofsky was drawn to the unsettling, macabre side of Surrealism,[7] initially creating gestural, expressionist renderings of grotesque, existentially angst-ridden figures in isolated or uncomfortable situations, that gave way in the 1960s to more fantastical, observational paintings that examined power, politics and domestic relationships in an unflinching way.

[22] Rosofsky wrestled with his experiences through intensely personal, penetrating, often brutal, imagery created in a staunchly figurative, gestural style that critics likened to June Leaf's, and described as a mix of expressionism and "surrealist hysteria.

"[23] The Chicago Tribune's Alan Artner called his sense of composition masterly, his palette subtle, and his way with the figure strong, but noted a tendency to overload his works that sometimes made them difficult to understand.

[11][17][2] A lifelong Chicagoan, Rosofsky is considered the post-war artist for whom Chicago—the lake, people, buildings, and abrasive character—was most integral, his bizarre figures and settings often bearing a specificity to the city's locales and conditions.

"[24] In the 1950s and early 1960s, Rosofsky often focused on nightmarish modern narratives that featured faceless men, often in hospitals, wheelchairs, and other uncomfortable, vulnerable situations or empty spaces, which he depicted in agitated lines that some critics liken to Alberto Giacometti's graphic work and Francis Bacon's tortured interiors (e.g., Patient in a Dentist Chair, 1961).

Time spent in Paris on a fellowship led to a greater surrealist turn in Rosofsky's work, realized in a fantastical, frightening vocabulary of clowns, menacing faces, and bizarre scenarios urgency and a more intense color palette.