This paper examines St. Urbain's Horseman and Barney's Version by Mordecai Richler as thematic twins, arguing that despite differences in narrative structure and chronology, both novels explore the interconnected themes of ageing, exile, and inheritance. Richler presents ageing not merely as a biological process but as a journey of self-reflection, memory, guilt, and reconciliation. Exile operates on multiple levels - geographical, cultural, psychological, and emotional - shaping the identities of the protagonists and their relationships with family, community, and history. Inheritance extends beyond material wealth to encompass cultural traditions, family legacies, moral responsibilities, and personal memories that define successive generations. Through irony, humour, and fragmented narration, Richler portrays individuals negotiating the tensions between personal freedom and inherited identity. By reading these novels together, the paper demonstrates how they function as complementary narratives that offer a profound meditation on memory, belonging, identity, and the complexities of the human condition in modern Jewish-Canadian experience