Through a consideration of the exchanges between John Cage and the Abstract Expressionist painters at Black Mountain College and The Club in the early 1950s, this article suggests a new reading of Abstract Expressionism that jettisons stylistic designations and typical postwar divisions to reveal the artists’ deep social concerns and critique of Cold War ideology. A shared interest in vitalism and Zen, evident in weekly discussions at The Club and in Harold Rosenberg’s definition of Action Painting, reveals the artists’ commitment to breaking down the barriers between art and life, a defining condition of postwar radicality more typically signaled by the work of Cage and Robert Rauschenberg.