The primary goal of the following article is to track the philosophy of the Beat Generation in the science fiction writing of Robert Anson Heinlein. The analysis is driven by the unique and unusual character of Heinlein’s novels, which is their emphasis on issues of rebellion, a critique of middle class culture, and negative commentary on the institutionalized Christian religion. The findings indubitably prove that Heinlein was in some way, directly or indirectly, affiliated with the ideology of the Beat Generation. The major themes that appear in his novels perfectly align with the issues raised by the Beatniks. Heinlein focused heavily on the search for identity, redefinition of the self in relation to the middle class background, and affiliation with the common and lowly. He also devoted much of his attention to the extensive analysis and critique of middle class culture, consumption and conformity. Finally, he rejected the legacy of the Christian religion and made negative comments on its conservative aspects. Respective sections of the paper focus on each of these major themes. The analysis concentrates on extracting those attributes that correlate to the major issues — rebellion against authority, middle class, and Christianity — and juxtaposes them against the ideology of the Beat Movement in search of parallels and similarities.