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Theo Angelopoulos's The Travelling Players (1975) and The Hunters (1977) have been widely characterized as Brechtian mainly because of the filmmaker's use of defamiliarization effects (V-effects) and the disrupted chronology in these films, but without close attention to the cinematic ways in which these films inflect, expand, and critique Brechtian aesthetics. Angelopoulos makes use of Brechtian techniques that invite spectatorial contemplation. In contrast to Brechtian epic theater, however, these two Angelopoulos films aesthetically and ideologically are characterized by melancholy and pessimism as opposed to Brecht's optimism and progressive view. After exploring the concept of left-wing melancholy, on the one hand, and Brechtian aesthetics, on the other, specifically Brecht's recommendations for a critically engaging theater that makes the audience think and respond, this article studies The Travelling Players and The Hunters in relation to Brechtian aesthetics to argue that they offer a cyclical view of history representative of left-wing melancholy as opposed to a teleological, progressive Brechtian view.