The hippie relationship to politics in the Sixties was complicated and ambiguous. Self-styled dropouts despised politics, but dropping out made a statement: no politics was a form of politics. “It was,” noted John Hopkins of London's IT underground newspaper, “alternative politics.” While hippies believed that the current “system” was rotten, they agreed on little else. Many were simple hedonists, most had no coherent ideology, others rejected politics as hopeless, and some had burned out after participating in protests. Both hippies and radicals disliked the status quo, but the counterculture's relationship with the New Left was strained. Hard to classify as left or right, freaks often disliked both the left's ideological rigidity and its agenda. Radicals advocated increased state power, but hippies were skeptical about all government. Thus, the two groups lacked much common ground. From 1966 to 1968, however, the Diggers and the Yippies challenged this conclusion, and a radical-hippie political alliance did emerge over People's Park in Berkeley in 1969.

In the Sixties some young people who opposed the existing order called themselves the New Left, radicals, or even revolutionaries. Some of these “politicos,” as they styled themselves, were Marxists, although they were seldom orthodox communists. They ranged from left-liberal advocates of an expanded welfare state to democratic socialists or Trotskyist, Maoist, and Castro-loving revolutionaries. Like hippies, leftists believed that American politics was corrupt and outdated. They especially criticized their elders for racism and for the Cold War, including the American war in Vietnam, which they saw as imperialist. At the same time, radicals believed in reason, science, and technology, whereas few freaks did. Leftists found hippies to be an embarrassment. Todd Gitlin, one of the founders of the New Left, disliked the counterculture's “frivolity.” Loathing young people who dropped out and ignored politics, radicals were often disgusted by self-indulgent drugs and sex. Young Communist Party members, in particular, wore short hair, avoided drugs, and were prudish about sex. No wonder communism was in decline.