The cultural role of Allen Ginsberg does not fit a typical Weberian model of charisma. The avant-garde poet was an outstanding personality and possessed an unusual ability to affect people. He played a vital role in expanding the boundaries of personal freedom in America of the 1950s–1990s, blazing new paths for spiritual, communal and artistic expression. Serving as a father figure for the counterculture—a symbol of an alternative set of cultural norms, lifestyles and literary forms—Ginsberg was a charismatic counter-leader, with no clearly defined followers or movement. As a leader in a more liberated era, he offered energy, ideas, inspiration, and color, but no structure or authority. Instead he was a prophet of freedom, calling on people to express themselves openly, to expand and experiment. This role demanded charisma but of a different kind—one that was more spiritual and less organizational or hierarchical. This article follows Gary Dickson’s essay “Charisma, Medieval and Modern,” in offering a suggestive analysis of and supplement to Weber’s understanding of charisma. The article grapples with the concept of charisma in relation to a generation that resented rigid structures and authorities.