Like many young Soviet composers during the post-Stalin Thaw, Arvo Pärt and Valentin Silvestrov experimented with a range of musical techniques in the 1960s before turning in radically simplified directions during the next decade. This paper explores for the first time the stylistic intersections and influences between Pärt and Silvestrov. Beginning in the 1960s, it traces the parallel paths of both composers, focusing on their liminal compositions—works sitting astride their avant-garde and simplified styles: chief among them Pärt’s Symphony No. 3 (1971) and Silvestrov’s Symphony No. 4 (1976). The contacts between Pärt and Silvestrov tell a particularly potent story about the dominant musical and sociopolitical trends and transformations from the 1960s through the present.