The mental–emotional sphere forms the highest and most individualising domain in homoeopathic case analysis. Over the last two centuries, the philosophical interpretation and clinical application of mental symptoms have undergone significant evolution, particularly through the works of James Tyler Kent, George Vithoulkas, and Rajan Sankaran. Each of these stalwarts represents a distinct epistemological phase in homoeopathic thought: Kent’s metaphysical and hierarchical approach, Vithoulkas’ clinical–constitutional synthesis, and Sankaran’s sensation-based and kingdom-oriented model. This review critically compares their conceptualisations of mental–emotional themes, analysing points of convergence, divergence, and clinical applicability. Classical texts, repertorial frameworks, and contemporary homoeopathic methodologies were systematically reviewed. The analysis reveals a gradual shift from moral–spiritual interpretation to experiential phenomenology and finally to deep vital sensation. Despite philosophical differences, all three approaches converge on the primacy of mental symptoms in remedy selection. The study underscores the need for integrative clinical reasoning that preserves Kentian structure, Vithoulkasian clarity, and Sankaran’s depth psychology. This comparative review contributes toward a more unified understanding of mental–emotional dimensions in modern homoeopathic practice.