Trilling published two complex studies of authors Matthew Arnold (1939) and E. M. Forster (1943), both written in response to a concern with "the tradition of humanistic thought and the intellectual middle class which believes it continues this tradition." His first collection of essays, "The Liberal Imagination", was published in 1950, followed by the collections "The Opposing Self" (1955), focusing on the conflict between self-definition and the influence of culture, "Freud and the Crisis of Our Culture" (1955), "A Gathering of Fugitives" (1956), and "Beyond Culture" (1965), a collection of essays concerning modern literary and cultural attitudes toward selfhood. In "Sincerity and Authenticity" (1972), he explores the ideas of the moral self in post-Enlightenment Western civilization. He wrote the introduction to "The Selected Letters of John Keats" (1951), in which he defended Keats’s notion of negative capability, as well as the introduction, “George Orwell and the Politics of Truth," to the 1952 reissue of George Orwell’s "Homage to Catalonia".