For Menand, there were worlds within worlds within the “Free World,” and each grappled with freedom differently. Even within particular spheres, there were fierce disagreements. George Kennan, for instance, imagined his Cold War foreign policy concept of containment as practical, flexible, realistic. Then he was critiqued by Walter Lippmann and others who thought it became ideologically rigid. Kennan was horrified. He had intended containment to be realpolitik. As Menand ruefully points out at the end of The Free World, containment ultimately led to the quagmire of the American intervention in the Vietnam struggle for national independence, precisely the kind of conflict Kennan wanted the US to avoid.
Many others—George Orwell, James Burnham, Jean-Paul Sartre, Simone de Beauvoir, Albert Camus, Hannah Arendt, Lionel Trilling, Norman Mailer, Susan Sontag, Claude Lévi-Strauss, Ira Berlin, James Baldwin, Franz Fanon, and Tom Hayden—continued these debates about politics, but increasingly the questions of containment and freedom also became dialogues about culture. What was actually existing freedom, not only politically but also personally? What was it not only in terms of policy, but also in terms of ideas, art, and lived experience? In the milieu of the visual arts, for instance, debates about representation, accuracy and their relationship to freedom raged as if they were as crucial as military maneuvers. Jackson Pollack, Lee Krasner, Clement Greenberg, Harold Rosenberg, Robert Rauschenberg, Jasper Johns, and others took turns making art, writing criticism, and framing approaches that addressed the relationship of reality and freedom, seeking not to contain things, as Kennan wanted to do with the Soviet Union and communism, but rather to emancipate the eye and mind from false perceptions. Kerouac and the Beats as well as DT Suzuki and John Cage embraced aleatory chance and improvisational spontaneity as paths to freedom. So too, in his way, did Elvis Presley and the 1950s teenagers who heard his music as liberating. This included the Beatles, who then joined the rock and roll parade, this “mass-market commercial product” exported transatlantically to Europe and back again to the US as a “hip and smart popular art form.”