The American counterculture of the 1960s and 1970s was a pivotal moment, not only in the American history but in that of the Western world. During the so-called “Woodstock years” the rejection of the cultural, political and social norms of the Age of Ike prevailed alongside with the experimentation of drugs and the sexual liberation. Hollywood provided “audiences with a new set of representations for constructing the world” (Ryan and Kellner 17). The purpose of the present paper is to show how, through two films and a new cinematic genre, Hollywood and the film industry not only illustrated the kaleidoscopic world of the counterculture but also played a major role as a vehicle of the countercultural movement. Stuart Rosenberg’s film Cool Hand Luke (1967) pictures the rejection of authority as well as the alienation felt by many youths at the time. As for Roger Corman’s film The Trip (1967) it portrays the prevalence of drugs and notably LSD which spawned the social and cultural upheaval of the epoch. Finally, I would like to shed light on a rather despised cinematic genre: pornography. Indeed, I want to show how hardcore pornography, with films such as Behind the Green Door (1972) and The Resurrection of Eve (1973), both produced by the Mitchell brothers, along with Joe Sarno’s softcore film Abigail Leslie is Back in Town (1974) not only reflected the sexual liberation but also laid emphasis on the question of women’s sexuality.