Drooker developed an early interest in graphic arts and cartoons, particularly the woodcut novels of Frans Masereel and Lynd Ward and the underground comics of Robert Crumb.

After studying sculpture at Cooper Union,[2] Drooker turned to poster art, creating flyers on local political issues while working as a tenant organizer.

His images, done in a striking black-and-white style reminiscent of Masereel and other 1930s expressionist illustrators, were widely copied and reused by others—sometimes for unrelated purposes such as advertising concerts—and were popular enough that he could make a small income selling artwork on the street.

During the 1980s, Drooker was further radicalized by his experiences with the police, due to their actions against squatters in the rapidly gentrifying Tompkins Square Park area and their increasing intolerance of unlicensed street artists and musicians.

In the 1990s, Drooker broadened his scope from graphic arts to painting, creating several covers for The New Yorker and a book of illustrations of Allen Ginsberg's poetry, Illuminated Poems.