The Liberal Imagination: Essays on Literature and Society (1950) is a collection of sixteen essays by American literary critic Lionel Trilling, published by Viking in 1950. The book was edited by Pascal Covici, who had worked with Trilling when he edited and introduced Viking's Portable Matthew Arnold in 1949. With the exception of the preface, which was written specifically for the publication of the book, all the essays included in The Liberal Imagination were individually published in the decade before the book's publication in literary and critical journals, such as The Partisan Review, The Kenyon Review, The Nation, and The American Quarterly. The essays represent Trilling's written work and critical thoughts of the 1940s.

In the essays, Trilling explores the theme of what he calls "liberalism" by looking closely at the relationship between literature, culture, mind, and the imagination. He offers passionate critiques against literary ideas of reality as material and physical, such as those he ascribes to V. L. Parrington, Theodore Dreiser, and the writers of the Kinsey Reports. He supports writers who engage in "moral realism" through an engaged imagination and a "power of love," which he sees expressed in works by Henry James, Mark Twain, Tacitus, F. Scott Fitzgerald, and William Wordsworth—and in the ideas of human nature in the works of Sigmund Freud.

The Liberal Imagination enjoyed a relatively large commercial success, selling 100,000 hardcover and 70,000 paperback copies, and was later to be understood as an essential book for a group of influential literary, political, and cultural thinkers of the era, called “The New York Intellectuals." The initial reviewers, such as Irving Howe, R. P. Blackmore, Norman Podhoretz, and Delmore Schwartz, represent the importance of this book to the "Intellectuals." In later years, scholars turned to The Liberal Imagination as a work representative of the post-war politics and culture of the United States, which was entering the early stages of the Cold War with the Soviet Union.

Trilling introduces the book, writing that though the essays that comprise the volume “are diverse in subject, they have…a certain unity.” The unity, he suggests, is an interest in liberalism. Trilling argues that because his contemporary America is predominantly tending to an intellectually liberal tradition, the lack of a robust conservative intellectual tradition causes the lack of a cultural dialectic, making liberal ideas also weak. He writes that a critical view on literature is the best way to “recall liberalism to its first essential imagination” because it is the “human activity that takes the fullest and most precise account of variousness, possibility, complexity, and difficulty.” In this way, Trilling introduces that his essays on literature will inevitably broach topics of culture, politics, and imagination.

Trilling confronts the influence of literary critic V.L. Parrington’s Main Currents in American Thought (1927), and the response to the novels of American writer Theodore Dreiser, to discuss what he sees as the dangerous consequences of a writer's supposed responsibility to a conception of reality as material and physical. Trilling argues that Parrington believed in a reality that is "immutable; it is wholly external, it is irreducible," and that Parrington believed the job of a literary writer to be the transmission of this reality by loyal reproduction. This conception of reality can turn Americans toward an unwarranted "sympathetic indulgence" of writers, such as Dreiser, who claim to represent material reality ("hard, resistant, unformed, impenetrable, and unpleasant.") when they are really representing an ideology of reality, such as Dreiser's nihilism. It also informs a disavowal of writers, such as Henry James, that engage in the "electrical qualities of the mind," and are not easily conformed to a social mission or politic.

Trilling addresses the literary work and career of novelist Sherwood Anderson, trying to reconcile his admiration for the man with the problems of his work. He assesses Anderson as victim to the fate "of the writer who at one short past moment has had a success with a simple idea which he allowed to remain simple and fixed." Trilling describes Anderson's "standing quarrel with respectable society" as one that once bred a truth related to the "precious secret essence" of individuals, but then led to a negation of the life of his characters through an excess of intellection, feeling, and a "love made wholly abstract." Trilling writes, "the more Anderson says about people, the less alive they become—and the less loveable." Though Trilling's evaluation of Anderson's truth is that it failed in literary expression—and that his lifeless worlds suggest a politic of subservient "marching men"—Trilling still admires the truthfulness of Anderson's "personal struggle with modernity," likening Anderson's work to an adolescence one must experience and eventually move on from.

Trilling sees Sigmund Freud’s psychology as the "only systematic account of the human mind which, in point of subtlety and complexity, of interest and tragic power, deserves to stand beside the psychological insights which literature has accumulated through the centuries." Trilling argues that Freud's relationship of influence with literature is reciprocal; that Freud was positivistic and rationalistic, and not devoted only to the "night side of life"; and that one can make a connection between Freud's conceptions of the dream, neurosis, and art to explain how an artist "is in command of his fantasy, while it is exactly the mark of the neurotic that he is possessed by his fantasy." Trilling rejects psychoanalytic readings of literary works that rely on an author's intention, and proposes that readers look for the "whole conception of the mind" implicit in a work's psychological "effects" and the psychological "temperament of the artist as a man." Trilling ends the essay reflecting on Freud's later work, in which the "death instinct" was introduced to complement the "pleasure principle," forming a state of man as "a kind of hell from within him from which rise everlastingly the impulses which threaten his civilization," where "compromise and the compounding with defeat constitute his best way of getting through the world." Thus, Trilling applauds Freud's tragic sense of the state of humanity.

Trilling places Henry James’s novel, The Princess Casamassima (1886), as among the greatest of novels from the nineteenth century. In his reading of the novel, Trilling points out James's "penetrating imagination" that gives an accurate account and imagining of not only the anarchy of the 1880s, but also the "social actuality" of anarchy's general moral claim on the goodness of humanity and the corruptive character of society. Trilling investigates the autobiographical aspects of the novel to conclude that the novel also acts as James's "demonstrative message," and that the artist possesses social responsibility. James's novel is an achievement of what Trilling calls "moral realism," which rests on James's "knowledge of complication," a penetrating awareness of "modern ironies," and an "imagination of disaster" complemented by an "imagination of love." Trilling concludes that James's moral realism in the novel results in an incomparable work that tells "the truth in a single luminous creation."