This chapter presents an account of the composer and conductor Leonard Bernstein, who, although constrained significantly by the ideological climate of the 1950s, refused to silence himself politically. Beginning in the last years of the decade, he became increasingly vocal in his support for New Left causes, including the antiwar, antinuclear, and civil rights movements. On State Department–funded conducting tours with the New York Philharmonic, he tried to use music, particularly the Americanist tradition, to challenge US foreign policy. In his compositions, he remained true to musical Americanism, striving earnestly in his art music to continue Copland’s prewar approach. He found a fruitful outlet for his political commitments in his works for musical theater, but his art music compositions present a much more complex and fraught picture. Bernstein was attempting to resist and undermine political nationalism, while simultaneously advancing cultural nationalism. But in the binarized climate of Cold War America, this would not prove easy.