San Francisco artist Bruce Conner established himself as a major figure in postwar underground cinema with his first film, A MOVIE (1958), a masterpiece of found-footage montage. Yet Conner also shot several films with his own camera, many of which feature a nude or partially clothed female performer and, in some cases, a pop music sound track; these films include COSMIC RAY (1961), VIVIAN (1964), EASTER MORNING RAGA (1966), and THE WHITE ROSE (1967). This essay examines a work by Conner that combines all of these elements, 1966's BREAKAWAY, an experimental dance film he made in collaboration with Los Angeles choreographer and actress Toni Basil. Shot over a period of two years in Santa Monica, BREAKAWAY draws from Conner and Basil's mutual involvement in both the Hollywood entertainment industry and the West Coast artistic underground through its curious fusion of pop and avant-garde sensibilities. This essay argues that BREAKAWAY is an inherently collaborative and cross-disciplinary work that self-reflexively invokes the utopian aspirations of the American underground and popular culture during the mid-1960s, especially through its utilization of rock and roll, a genre rooted in vernacular African American music. To unpack these connections, BREAKAWAY is analyzed in the context of two contemporary films in which Basil played significant roles: The T.A.M.I. Show (dir. Steve Binder, US, 1964), a groundbreaking concert film that signaled a new era of on-screen racial integration, and the classic psychedelic road movie Easy Rider (dir. Dennis Hopper, US, 1969).