Organized as part of the annual Art Days festival in the capital of the Latvian SSR, the First Exhibition of Approximate Art comprised a cacophonous and provocative mashup of music, dance, performance art, and design. At the center of the event was a demonstration of mixing and scratching records by Maximilian Lenz, also known as Westbam, one of the leading DJs in West Berlin. Mining archival sources in Berlin and Riga, this article reconstructs the complicated path by which the DJ came to perform at the event. It reveals a surprising network of relations and alliances operating in tandem behind the scenes, featuring a Riga artist dedicated to enacting a vision of postmodern performance in his city, an ambitiously networking émigré Latvian living in exile in West Germany, and a pair of Soviet offices under direct control of the KGB, charged with managing cultural exchanges with the West in hopes of currying sympathies for Soviet culture and policy. Complementing and extending research on the “gaps” and “holes” in the Soviet system that sometimes allowed for the staging of otherwise unacceptable works of art, the story of the First Exhibition of Approximate Art reveals how personal connections and interpersonal networks within even the most highly monitored parts of the system itself—the state security apparatus—could open doors for artistic projects unanticipated and even undesired by the bureaucratic state.