Here I investigate the historical confluence of therapeutic culture, counterculture, and folk rock in late-1960s and 70s America. The Old Left communists of the 1930s popularized folk music as a political genre protesting systemic inequality. Then in the early-1960s, the New Left revived folksongs to protest racial inequality and the Vietnam War, among other causes. By the late 60s, though, some folk artists made interiority their hip “protest.” As many folksingers transitioned to folk rock, American culture was becoming more therapeutic, and folk rock artists like James Taylor, Joni Mitchell, and Jackson Browne, started writing lyrics preoccupied with interior pain—“inner poverty”—more than economic poverty. Treating the early albums of Taylor, Mitchell, and Browne as ideologically rich texts for cultural and literary studies, I examine the way that folk rock promoted—and sometimes self-reflexively critiqued—therapeutic perspectives that are associated with a political stance, but that also helped consumers evade external social, economic, and political issues. These singer-songwriters use images of the road and nature to evoke—and at times question—therapeutic individualism and ostensible anti-consumerism. In addition they romanticize love and music as therapeutic opportunities to express compensatory “depth,” but they also scrutinize the mass-commercialization of love and music. Their lyrics offer insights into the Woodstock to Watergate forms and operations of “soft capitalism.”