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This chapter analyses the traces left by the Beat movement in Estonian literature. It discusses Estonian Beat writers Johnny B. Isotamm, Peeter Sauter and Jürgen Rooste, who followed mainly the idea of bringing literature “back to life.” In addition, it introduces writers whose works were indirectly connected to the Beats and who valued the idea of a search for an inner enlightenment (Mati Unt, Jaan Kaplinski). Around 1965–1975, ideas of the Beats came indirectly into Estonia through the counterculture, the hippie movement, and the new youth culture. In the 1990s, translations of canonical Beat works were published and Jack Kerouac and Allen Ginsberg influenced young Estonian writers. Both periods valued authenticity, freedom, sincerity and honesty, but with a different emphasis. This chapter also provides brief overviews of Estonian culture and literary life in both eras.