This paper is about 1960s counterculture, the role of psychedelic drugs, and their representations in film and literature of the decade. Psychedelic substances are relevant for this era because they played an important role in the 1960s countercultural movement and were featured in a variety of musical, literary, and film works. The substances sometimes also influenced the authors and the content of the art which is one of the reasons for taking a close look at their representation in the artefacts. This paper analyses three case studies - Thomas Pynchon’s novel The Crying of Lot 49 (1966) and two films, Roger Corman’s The Trip (1967) and Dennis Hopper’s Easy Rider (1969) - and considers which psychedelic substances are considered and how they are represented as well as how the counterculture and the hippie subculture are portrayed. The case studies were analyzed by utilizing both qualitative and comparative methods. Psychedelic substances, as well as other non-psychedelic ones, are featured in both films and the novel. The references to counter-culture are more explicit in the films, while the novel acknowledges the counterculture in an indi-rect way through the subversive subplot with an alternative postal system and those who use it. The Trip, on the other hand, completely revolves around an LSD trip and its effects and the after-math while set in a typical countercultural environment of young people dressed in hippie fashion and smoking marijuana. Finally, Easy Rider also directly references the counterculture and the hippie movement in various aspects, such as communal lifestyle and values, as shown in this paper. All three selected case studies do not glamorize nor do they promote psychedelic drug use as such, rather, they show that the substance use is deeply connected with the anti-establishment cul-ture it was a part of.