In 1992, he began teaching in the Visual and Cultural Studies Program at the University of Rochester, where he was the Fanny Knapp Allen Professor of Art History.

In 1977, he curated the influential exhibition Pictures at Artists Space, presenting the early work of Sherrie Levine, Jack Goldstein, Philip Smith, Troy Brauntuch, and Robert Longo.

Two years later, he elaborated the discussion of postmodern artistic strategies in an essay with the same title in October, including Cindy Sherman in what came to be known as the "Pictures Generation."

In 1985, Crimp was one of numerous art critics, curators, and artists who spoke at a General Services Administration hearing in defense of Richard Serra's controversial public sculpture Tilted Arc, which had been commissioned as a site-specific piece for Federal Plaza in New York City and was ultimately removed in 1989.

Feminist scholar Diana Fuss and cultural critic Phillip Brian Harper urged Crimp to publish his notes "over dinner one summer evening."

[10] The book begins in his hometown in Idaho, where he escapes to New York to write criticism for ARTnews while working at the Solomon R. Guggenheim Museum.

Crimp details his days working at the Chelsea Hotel for designer Charles James, spending his evenings watching film and ballet, and co-founding the art journal October.