Oldenburg was born in Stockholm, Sweden, but moved to America as a child in 1936. He studied at Yale University and the Art Institute of Chicago. One of his first large works was Lipstick (Ascending) on Caterpillar Tracks, originally installed in Beinecke Plaza at Yale, and now residing in the Morse College courtyard.
He has collaborated since 1976 with Dutch/American pop sculptor Coosje van Bruggen. They were married in 1977.
In addition to freestanding projects, he occasionally contributes to architectural projects, most notably the Chiat\\Day advertising agency headquarters in the Venice district of Los Angeles, California -- the main entrance is a pair of giant black binoculars.