Claes Oldenburg, Lipstick Ascending on Caterpillar Tracks, 1969
From Art History, Volume II by M. Stokstad:
Oldenburg’s humor is much evident in this large-scale public work at his alma mater, Yale University. Oldenburg created this sculpture at the invitation of a group of architecture graduate students - who requested a monument to the “Second American Revolution” of the late 1960s, marked by student demonstrations against the Vietnam War. The lipstick tube, mounted on Caterpillar tractor tracks, suggests a grounded missile and subverts the warlike reference by casting the missile in a cosmetic, feminine form. Oldenburg also addresses sexual and military potency and gives the lipstick a balloon-like vinyl tip which is meant to deflate slowly after it is pumped with air.