Throughout history, mankind's ideal to pursue what he reveres as freedom has proved unattainable since insurmountable obstacles have always impeded the path to freedom. Individual freedom has constantly been restricted by external forces, in most cases an authority that forces humans into submission and bondage in a way they find themselves not only physically but also spiritually constrained by these shackles. In some instances, the magnitude of the authoritative force is so considerable that the individual surrenders his freedom and abandons any hopes of liberation. One of the theorists who highly values individual freedom is the German social psychologist Erich Seligman Fromm(1900-1980). He asserts in his book Escape from Freedom (1941) that achieving freedom has been a prime goal for mankind throughout time. He maintains that as an individual unshackles himself from the restrictions of an authority, he tries to compensate for the lack of security which stems from his rejection of that authority and thus submits himself to another source of authority or becomes an authoritative figure himself. This paper aims to analyse Fromm's concept of freedom in Anthony Burgess's A Clockwork Orange (1962). Through the application of Fromm's theories, this article attempts to show that freedom is not merely a release from external forces but a release from internal constraints as well, stressing the fact that spiritual freedom is the real path to happiness and internal satisfaction and that positive freedom is from within and not without.