Background. A philosophy of life serves as a framework for constructing a worldview and a moral compass for human beings; traces of such a philosophy are often found in literary works. Purpose: This study examines philosophies of life in Javanese and Russian traditions through comparative cultural philosophy and hermeneutics, interpreting and comparing three dimensions: cultural values, spirituality, and existentialism. Method: This descriptive qualitative study analyzed three Javanese piwulang texts (Serat Wulangreh, Serat Wedhatama, Serat Kalatidha) and three Russian novels by Tolstoy and Dostoevsky (Anna Karenina, The Brothers Karamazov, Crime and Punishment). Data were collected through close reading and note-taking, then analyzed in four steps: coding passages on cultural values, spirituality, and existence; interpreting them within their religious and historical horizons; comparing the coded passages across traditions; and drawing conclusions on convergence and divergence. Results: Serat Wulangreh stresses etiquette, careful selection of teachers, and self-restraint to maintain social harmony (rukun); Serat Wedhatama locates evil in the ego (angkara) and offers the curbing of desire toward manunggaling kawula Gusti; Serat Kalatidha answers a morally corrupt age with eling lan waspada (mindfulness and vigilance). In the Russian novels, Anna Karenina shows how unchecked desire leads to emptiness while Levin finds meaning in living “for the soul”; Crime and Punishment presents confession and suffering as the road to Raskolnikov’s renewal; and The Brothers Karamazov defends inner freedom against the rationalized authority of the Grand Inquisitor. Overall, the Javanese texts portray a preventive philosophy of life, whereas the Russian novels portray a reflective one in which suffering and atonement become the path to spiritual transformation, rooted in Orthodox Christianity. Conclusion: Despite developing in vastly different geographical, historical, and religious contexts, both traditions reject pure materialism and rationalism and hold that a meaningful life is achieved through an inner process oriented toward God and communal life. This study helps fill a gap in cross-cultural research on Javanese and Russian philosophy, which have largely been studied in isolation.