Bisexuality occupies a contested and generative position across the depth-psychology corpus, functioning simultaneously as a biological hypothesis, a metapsychological principle, and an archetypal configuration. Freud introduced it as a foundational premise: every human organism carries a constitutional double disposition, masculine and feminine, whose unequal resolution shapes object-choice, neurotic structure, and the fate of the Oedipus complex. His 1905 ‘Three Essays on the Theory of Sexuality’ treats bisexuality both as an explanatory key to inversion and as evidence that the sexual instinct is, in its origins, independent of any fixed object. Hillman’s archetypal revision subjects the Freudian framework to mythic elaboration: in ‘The Myth of Analysis’ he identifies bisexuality with the Dionysian libido itself — a double current that unites not merely male and female but also life and death, activity and passivity. For Hillman, bisexual consciousness becomes the telos of analysis; repudiation of the feminine is the very bedrock of neurosis, and cure coincides with the integration of that which has been held in contempt. Klein approaches the term from the angle of internal object relations, locating bisexual identifications — wishes to be the other sex, to possess the other parent’s attributes — within the interplay of envy, admiration, and the drive toward integration. Winnicott reformulates the question clinically as the problem of the ‘split-off’ contra-sexual element, examining what it means for a man to carry an unacknowledged girl-self. Samuels maps the post-Jungian debate, tracing bisexuality’s conceptual cousins — androgyny, polymorphous perversity, polyvalent germinal disposition — across schools. Together these voices reveal an enduring tension between biological grounding and psychological symbolism.