Edward Estlin Cummings (1894-1962) was brought up in a conservative Cambridge, Massachusetts home. His father, with degrees in both philosophy and divinity, taught at Harvard University until 1900 when he received ordination by the Unitarian Church and became a pastor at the South Congregational Church of Boston.

According to family diaries, Cummings wanted to be a poet from an early age. He was supported in this ambition by his mother who made up word games and other activities to encourage his creativity. Cummings also drew prolifically, and his childhood drawings were often inspired by literature; his drawings included storyboards. Cummings attended public schools, including the Cambridge High and Latin School, prior to entering Harvard in 1911. While there, he concentrated in the classics, including Latin, Greek, and literature, and he mastered the various forms of poetry, gaining the foundation he needed in order to begin the experimentation with poetic form and shape that became his trademark.

While at Harvard, Cummings published poetry in the and the Through these organizations he became acquainted with S. Foster Damon, Stewart Mitchell, John Dos Passos, Scofield Thayer, and J. Sibley Watson. These friends would encourage and support Cummings through much of his artistic career; many of them also shared his interest in the visual arts as well as poetry and literature. Damon, a music student, introduced Cummings to the works of El Greco, William Blake, Paul Cézanne, James McNeill Whistler, the French Impressionists, and the Fauves. He took Cummings to the Armory Show of 1913 when it was in Boston, and there Cummings became excited by the Brancusi sculptures. Through Thayer, Cummings became acquainted with the works of Picasso, Toulouse Lautrec, Beardsley, the Post Impressionists, and the Cubists. While still in school, Thayer gave Cummings a copy of Willard Huntington Wright's which Cummings annotated extensively. John Dos Passos also painted and drew. Cummings never had formal art lessons, but he learned new oil painting techniques from his Harvard group of friends.

Cummings earned his BA from Harvard in 1915, magna cum laude, like his father before him, and was invited to speak at the commencement ceremony. He presented a term paper on This paper demonstrated Cummings' affinity with the modern artistic sensibility, especially his interest in the overlap between the visual arts and literature, a keystone in his distinctive typographical style.

After finishing his Master's degree in 1916, also from Harvard, Cummings moved to New York City in January of 1917. He worked at P. F. Collier for a few weeks, but became bored and quit, deciding instead to pursue the freedom of life as a full-time artist and poet. At this time he was painting in a cubist style. In April, he volunteered for the Norton-Hajes Ambulance Service and shipped out for France. On the trip he met William Slater Brown and their friendship was cemented by an unexpected five weeks of free time in Paris awaiting the rest of their ambulance unit.

Several months later, events took a defining turn for Cummings when he and Brown were detained by the French military on suspicion of espionage and undesirable activities. As a result of censor-provoking letters home by Brown and a preference for the company of French soldiers over their fellow American ambulance drivers, the two young men were held for three months in a concentration camp at La Ferté Mace. They were kept, along with their fellow detainees, in a large room which was represented in the title of Cummings' book about this experience, (1922). Cummings' father worked through diplomatic channels and finally wrote a letter to President Wilson to obtain Cummings' release in December 1917. Brown was released two months later. Cummings returned to the United States, first to his parents' home in Massachusetts and then to New York, where he was joined by Brown.

For the next several years, Cummings painted and wrote. His paintings were now inspired by what he had seen in Paris, and a futurist influence started to appear. In 1919 he entered two paintings in the spring show of the New York Society of Independent Artists, and Gaston Lachaise (whom Cummings had met through Lachaise's stepson, Edward Pierce Nagle) reported to Cummings that Albert Gleizes had expressed enthusiasm about Cummings' paintings. In 1920 he again entered two large paintings in the society of Independent Artists exhibition, which were mentioned favorably by S. Jay Kaufman in the . In 1921 he entered his painting in the Independent exhibition, but this painting was attacked in a New York newspaper review of the show.

In 1924, he married Elaine Orr Thayer, the mother of his daughter Nancy. They divorced after two months and in 1929, Cummings married Anne Minnerly Barton. They spent much of the next two years living and traveling in Europe.

In May 1931, Cummings left Barton and traveled to the Soviet Union. Pre-disposed to enjoy the trip, Cummings found his personal sense of individualism disturbed by the lack of intellectual and artistic freedom that he found. He published his diary from the trip under the Greek title (1933), which translates to

In August 1931, Cummings exhibited 162 works at a show arranged by Philip Kaplan at the Kokoon Arts Club in Cleveland, Ohio. His book , a collection of works in charcoal, ink, oil, pastel, and watercolors, was published in 1931.

In 1932, while his divorce from Barton was being settled, Cummings met Marion Morehouse, who was to be his companion and common law wife for the rest of his life. In 1933, Cummings received the Guggenheim Fellowship for the purpose of writing a "book of poems." In 1935, unable to find a publisher for his book, he published (1935) with the help of his mother. It was dedicated to the fourteen publishing houses that had turned him down.

E. E. Cummings continued to produce a steady stream of poems and publications throughout the forties and fifties. In 1952, Harvard offered him the Charles Eliot Norton Professorship for the 1952-53 school year. Also during the fifties, Cummings began to tour, reading his poetry across America. In 1958, he won the Bollingen Prize for Poetry from Yale University and published his final volume of new poems, .

He died at his family farm on September 3, 1962.

Critics have generally divided Cummings' career as a painter into two stylistic phases. The first phase, about 1915-1928, was represented by his experimental large-scale abstracts and his drawings and caricatures published in . During the 1920s Cummings started to drop out of the gallery scene, and he came to view the art establishment as anti-intellectual. The second phase of his art was from about 1928 until his death; this phase was characterized by representational works: still lifes, landscapes, nudes, and portraits.