In the fall of 1968, a group of Yale students and faculty calling itself the Colossal Keepsake Corporation approached Swedish-born American Pop artist Claes Oldenburg about creating a monumental public sculpture on Yale's campus.
Oldenburg, a Yale alumnus known for his whimsical sculptures of everyday objects, embraced the idea. Waving any fee for his services, he produced a characteristically fanciful design: a gigantic tube of orange-colored lipstick set on caterpillar tracks.
The corporation, composed of graduate students in art and architecture and supported by architectural historian Vincent Scully, another faculty member, a Yale alumnus, and Oldenburg himself, raised $5,000 in donations to pay for the materials needed to build the sculpture. The sculpture's components were fabricated at cost at Lippincott, Inc., a North Haven-based company that has helped artists build large-scale public sculptures since 1966.
On May 15, 1969, Oldenburg and the students installed the piece, "Lipstick (Ascending) on Caterpillar Tracks," on Beinecke Plaza as a surprise "gift" to the university. It stood on the plaza for about a year before the artist had it removed. A refurbished version of the sculpture returned to campus in 1974 as a gift to the Yale University Art Gallery and was installed in the courtyard of Morse College, one of Yale's 14 residential colleges, where it remained as a long-term loan for most of the next half century.