Oldenburg is a Sweden-born sculptor famous for his large-scale public installations, often made from everyday items. His family moved to the United States when he was young, and he would eventually attend Yale and then the Art Institute of Chicago, where he studied under Paul Wieghardt. He worked in Chicago for several years and opened a studio there before moving to New York City in 1956.

In the 1960s, he became involved with the Pop Art movement made famous by Andy Warhol, and he attended many performance-oriented gatherings which would later influence his own work. His massive sculptures, for which he became best-known were often displayed publically and frequently featured interactive components. His 1974 work Lipstick (Ascending) on Caterpillar Tracks featured a giant tube of lipstick that would deflate unless an viewer pumped air into it, and was displayed at Yale University for years and now resides in the Morse College courtyard. Other famous pieces include Soft bathtub (model) – Ghost Version, a large and loosely hanging sculpture made on a foam-filled canvas out of wood, cord and plaster.

In 1976, he married pop sculptor Coosje van Bruggen with whom he has collaborated with on more than 40 large-scale projects, creating works like the 1999 sculpture Typewriter Eraser, Scale X, an enigmatic piece that roughly resembles a giant radish with blue rope coming out its top. He has also involved himself in a few architectural projects including the construction of an advertising agency in Los Angeles whose entrance is a set of massive binoculars.