His prodigious and innovative body of work included assemblages, collages, drawing, and painting, as well as designs for book and album covers, theatrical sets and costumes.

[3] Brainard became friends with Ron Padgett, Dick Gallup, and Ted Berrigan during high school while working on the literary journal The White Dove Review, which was printed five times during 1959/1960.

After high school, the artist re-united with the White Dove boys in New York City shortly after leaving the Dayton Art Institute.

[4][5] By 1964, Brainard had already had his first solo exhibition and was ensconced in a circle of friends that included Frank O'Hara, Kenneth Koch, Alex Katz, Edwin Denby, Larry Rivers, Fairfield Porter, James Schuyler, Jane Freilicher, Virgil Thomson, John Ashbery, among many others.

The same qualities shine forth in all that he produced: clarity, bold simplicity, accuracy of execution and feeling, humor, casual elegance, a charm that invites his audience in rather than keeping them at arm's length, and something grander but determinedly low key and offhand, a sense of the ordinary as sacramental.Particularly in the collages, drawings and small works on paper, Brainard transformed the everyday into something revelatory: [Brainard] seems to have been drawn to forms of containment, in which the unruly or rupturing experiences of life are brought into the kind of reductive clarity that we often associate with classical modalities.

... Not surprisingly, along with this gift for distillation, Brainard had an uncanny eye for essential, revelatory detail; these contribute to the vivid immediacy and spontaneity of his work.

His deft juxtapositions of the banal with the revelatory, the very particular with the apparently universal accumulate into a complex depiction of his childhood in the 1940s and '50s in Oklahoma as well as his life in the '60s and '70s in New York City.