The aim of the study was to discuss Ukrainian literary dissent as a component of the socio-cultural phenomenon of the Sixties – the national revival of the 1960s and 1970s in Ukraine and the Resistance Movement under the totalitarian regime of the Soviet Union. The objective was to reflect on the phenomenon of Ukrainian literary dissent in the second half of the twentieth century in the light of the modus operandi/concept of Freedom. Historical and literary, comparative and historical, receptive and aesthetic, on top of typological methods are tools for understanding the Ukrainian literary dissent of the 1960s and 1970s in Ukraine in its morphological dimension. Personalities of the Ukrainian literary dissent included Ihor Kalynets, Hryhorii Kochur, Yurii Lytvyn, Valerii Marchenko, Taras Melnychuk, Mykhailo Osadchyi, Vasyl Ovsiienko, Mykola Rudenko, Yevhen Sverstiuk, Ivan Svitlychnyi, Vasyl Stus, Oleksa Tykhyi, Les Taniuk, Mykola Kholodnyi, and others. The basis for the formation and existence of Ukrainian literary dissent (general historical, historical and cultural, mental, ontological) in the context of the Sixties as a “synergistic phenomenon” was discussed by Liudmyla Tarnashynska. Worldview, philosophical, socio-cultural manifestations of Ukrainian literary dissent were literary aspects of the human rights movement (literary and artistic, rhetorical and journalistic, literary and critical). The existence of Ukrainian self-publishing was a special form of the Resistance Movement of the 1960s and early 1970s, as well as an alternative component of the literary process of this period (Ivan Dziuba, Iryna Zhylenko, Sviatoslav Karavanskyi, Roman Korogodskyi, Mykhailyna Kotsiubynska, Leonid Pliushch, Mykola Rudenko, Yevhen Sverstiuk, Ivan Svitlychnyi, Vasyl Stus, and others). Contribution of literary dissidents included the activities of the Ukrainian Helsinki Group (Oles Berdnyk, Yurii Lytvyn, Valerii Marchenko, Mykola Rudenko, Vasyl Stus). The activity of the Ukrainian literary dissent is projected into the plane of Freedom and Rebellion in the socio-historical, mental, genetic, and metaphysical planes were social freedom as a socio-political struggle; personal freedom as an existential confrontation; and creative freedom as a metaphysical rebellion. Presentation of the activities/works of Mykola Rudenko, Ivan Svitlychnyi, and Vasyl Stus as key figures of Ukrainian literary dissent follows.