He moved to New York City after college to make movies, and did find work in documentary films, an occupation he still pursues.

This series and Little, Big were cited when Crowley received the prestigious American Academy of Arts and Letters Award for Literature.

A museum-quality 25th anniversary edition of Little, Big, featuring the art of Peter Milton and a critical introduction by Harold Bloom, is now complete.

[6] In 1989 Crowley and his wife Laurie Block founded Straight Ahead Pictures to produce media (film, video, radio and internet) on American history and culture.

Crowley's short story "Flint and Mirror" (2018) was presented as "recently discovered among uncatalogued papers of the novelist Fellowes Kraft" (one of the Ægypt's protagonists).

Crowley's articles and essay-reviews have appeared in Lapham's Quarterly, the Boston Review, Tin House, and Harper's.