It is in Cummings' portraiture that he reveals his most meticulous craftsmanship as a painter--it would often take over twenty separate sittings for Cummings to be completely satisfied with a portrait. Included here are a large number of paintings of his third wife, Marion Morehouse Cummings, who in her unmarried days had been a famous New York fashion model, as well as a model for the modernist photographer Edward Steichen. Also included are many various portraits, including renderings of his mother, Rebecca Haswell Cummings; his second wife, Anne Barton Cummings; his daughter, Nancy; and portraits of friends such as Stewart Mitchell, Alice James, Joe Gould, Stephen Barr, Kenneth Burke, and Scofield Thayer.

In his essay, "E. E. Cummings, Painter," Rushworth M. Kidder notes that Cummings "ran counter to the direction one might expect of so experimental a poet: beginning as a creator of abstract canvases, he ended up as a representational painter." Pointing out that Cummings was a meticulous craftsman, an assiduous experimenter, and a rigorous theoretician whose thousands of pages of notes on color and art are now in the Houghton Library at Harvard University, Kidder concludes that he was "nothing if not serious" about his painting, and that "not surprisingly, some of Cummings' most able works are portraits. That he was a methodical craftsman, carefully planning and executing each portrait, is evidenced by the number of preliminary studies he was willing to make." Kidder makes the case strongly that Cummings' visual and literary work should be seen as being of a piece: the early, more dramatic experimentation in both areas yielded in his later life to less overt, more subtle inquiries, which were buttressed by his careful attention to craft.

In a letter written late in his life to his German translator, Cummings wrote that his painting "'pushes abstraction beyond the abstract' and returns to Nature," and he elsewhere stated that "as soon as you cut yourself off from nature, all you get is decoration." Cummings' rejection of the abstract art of the 1920s and '30s was rooted in contempt for the school of thought that argued that artistic value and intellectual rigor were mutually exclusive: the intellectual element of art was what allowed the aesthetic elements to approach that which was of lasting value and not just momentarily pleasing. He viewed representational painting as more challenging than abstract art and derided the "super-submorons" who worshipped Picasso, ignoring the fact that their hero had "once declared that there's no such thing as 'abstract' painting & cried out 'respect the object'."