Born in Stockholm, Sweden, Oldenburg spent his early life in Sweden, Norway, New York, and Chicago, before attending Yale University and the Art Institute of Chicago. Throughout his early career, the artist experimented with various styles of sculpture, beginning with soft sculpture made of fabric, then pieces created out of cardboard, burlap, and newspaper containing simple figures, letters, and signs. He then shifted to creating sculptures out of chicken wire frames covered in plaster-soaked canvas and enamel paint, which depicted large everyday objects.
While living in New York in the 1950s, Oldenburg became fascinated with aspects of street life like store windows, graffiti, advertisements, and trash, leading him to transition from painting to sculpture as his primary art form. He was associated with the Pop Art movement of the 1960s, during which time he created “happenings” or experimental performance art productions using sound, movement, objects, and people.
In the mid-60s, Oldenburg would create his first monument, Lipstick (Ascending) on Caterpillar Tracks, which was placed surreptitiously on the Yale University campus, later finding a permanent home at Morse College, elsewhere on campus. This led to a series of monuments including Clothespin in Philadelphia, Colossal Ashtray with Fagends in Paris, and Batcolumn in Chicago.
After marrying his second wife, Coosje van Bruggen, the couple began collaborating on projects. Together, they created large-scale sculptures like Spoonbridge and Cherry for the Minneapolis Sculpture Garden, Dropped Cone in Cologne, Germany, and Tumbling Tacks at the Kistefos Museum in Jevnaker, Norway.