This text is an innovative exploration of philosophy and madness in the context of the critical engagement of Heidegger’s phenomenological ontology with Freudian psychoanalysis. Included is a play in which, after a mental breakdown, Martin Heidegger undergoes psychoanalytic treatment from Dr. Medard Boss. Boss is essentially caught between two intellectual giants: his patient, Heidegger, who challenges him to evolve beyond traditional Freudian psychoanalysis, and his mentor, Freud, who acts as a “ghostly” consultant in facilitating Heidegger’s return to health. The dialogue of the play consists of actual quotes taken from the major thinkers themselves, which enhances the authenticity of this fictitious production. In addition, the theoretical perspectives of Freud, Heidegger, Boss, and Ludwig Binswanger are included to enhance the readers’ background knowledge. In the process of disclosing these brilliant theorists, this book uncovers what each orientation has to offer the others.