Upside Down City is a prop, a painting, a relic, and a sculpture. It is among the first of Claes Oldenburg's famous "soft sculptures" in which he took everyday objects such as hamburgers or electric plugs and transformed their scale, texture, and mood. Seeking to reimagine the subject of art, Oldenburg embraced the "poetry of everywhere" and infamously announced in a 1961 manifesto, "I am for an art that takes its form from the lines of life itself . . . that does something other than sit on its ass in a museum."

In 1962, Oldenburg organized a series of events in New York City's East Village in a rented store he called the Ray Gun Manufacturing Co. The performances were not narrative but associative, and sometimes deliberately provoked the discomfort of the tightly packed audience standing amid the action. Playfully alluding to the upcoming 1964 New York World's Fair in Flushing Meadows, Oldenburg's final event, World's Fair II, was deliberately lowbrow, ending with the performers hanging Upside Down City from the ceiling, set to the tune of a slowed-down recording of a Scottish bagpipe march.