He was the managing editor of Vanity Fair in 1920 and 1921, and later served as Associate Editor of The New Republic and as a book reviewer for The New Yorker. His works influenced novelists Upton Sinclair, John Dos Passos, Sinclair Lewis, Floyd Dell, and Theodore Dreiser. He wrote plays, poems, and novels, but his greatest strength was literary criticism.
Axel's Castle: A Study in the Imaginative Literature of 1870-1930 (1931) was a sweeping survey of Symbolism. It covered Arthur Rimbaud, Auguste Villiers de l'Isle-Adam (author of Axel), W. B. Yeats, Paul Valéry, T. S. Eliot, Marcel Proust, James Joyce, and Gertrude Stein.
In his landmark book To the Finland Station (1940), Wilson studied the course of European socialism, from the 1824 discovery by Jules Michelet of the ideas of Vico culminating in the 1917 arrival of Lenin at the Finland Station of Saint Petersburg to lead the Bolshevik Revolution.
Wilson was interested in modern culture as a whole, and many of his writings go beyond the realm of pure literary criticism. His early works are heavily influenced by the ideas of Freud and Marx, reflecting his deep interest in their work.
Wilson's critical works helped foster public appreciation for U.S. novelists Ernest Hemingway, John Dos Passos, William Faulkner, F. Scott Fitzgerald, and Vladimir Nabokov. He was instrumental in establishing the modern evaluation of the works of Dickens and Kipling.
Edmund Wilson attended Princeton with Fitzgerald, who referred to Wilson as his "intellectual conscience". After Fitzgerald's early death (at the age of 44) from a heart attack in December 1940, Wilson edited two books by Fitzgerald (The Last Tycoon and The Crack-Up) for posthumous publication, donating his editorial services to help Fitzgerald's family. Wilson was also a friend of Nabokov, with whom Wilson corresponded extensively and whose writing Wilson introduced to Western audiences. However, their friendship was marred by Wilson's cool reaction to Nabokov's Lolita and irretrievably damaged by Wilson's public criticism of Nabokov's eccentric translation of Pushkin's Eugene Onegin.
Wilson was often rather indifferent to the pain that his vigorous criticism might bring to others. This was only a minor problem in his role as a literary critic, but in personal relationships it was more costly. He had many marriages and affairs. His first wife was Mary Blair, who had been in Eugene O'Neill's theatrical company. Second wife Margaret Canby was described as a charming, cultured lady who regarded Wilson as more of a friend. After her death in a freak accident two years after their marriage, Wilson wrote a long eulogy to her and said later that he felt guilt over having neglected her. From 1938 to 1946 he was married to Mary McCarthy, who like Wilson was well-known for her literary criticism. She admired enormously Wilson's breadth and depth of intellect, and they co-operated on numerous works. In an article in The New Yorker, Louis Menand says "The marriage to McCarthy was a mistake that neither side wanted to be first to admit. When they fought, he would retreat into his study and lock the door; she would set piles of paper on fire and try to push them under it." He wrote many letters to Anaïs Nin, criticizing her for her surrealistic style as opposed to the realism that was then deemed correct writing, and ended by asking for her hand, saying he would "teach her to write", which she took as an insult. He later married Elena Mumm Thornton (previously married to James Worth Thornton), but continued to have extramarital relationships.
Wilson was also an outspoken critic of U.S. Cold War policies. He did not pay his USA federal income tax from 1946 to 1955 and was later investigated by the IRS. Opinions vary on his motives, but he also failed to pay his state income taxes during this period, which had little to do with the Cold War.
After a settlement, Wilson received a $25,000 fine rather than the original $69,000 sought by the IRS, perhaps due to his political connections to the Kennedy administration. He received no jail time. In his book The Cold War and the Income Tax: A Protest (1963), Wilson argued that, as a result of competitive militarization against the Soviet Union, the civil liberties of Americans were being paradoxically infringed under the guise of defense from Communism. For these reasons, Wilson also opposed U.S. involvement in the Vietnam War.
Wilson's view of President Lyndon Johnson was decidedly negative. Historian Eric Goldman writes in his memoir The Tragedy of Lyndon Johnson that when Goldman, on behalf of President Johnson, invited Wilson to read from Wilson's writings at a White House Festival Of The Arts in 1965: "Wilson declined with a brusqueness that I never experienced before or after in the case of an invitation in the name of the President and First Lady."