Many of the characters in Stephen Sondheim's musical theater are burdened with a character pathology which results in their inability to establish intimate relationships. Drawing on Freud's “Psychopathic characters on the stage” and psychoanalytic theory, this article suggests that developmental, biological, and environmental factors from Sondheim's childhood contribute to his characters'social and interpersonal alienation. Sondheim's art is a partially successful attempt to re-assert connections and repair narcissistic injuries, introjecting the absentmother as part of the superego. The resistance to dramatizing character pathology through biography is both an expression of society's postmodern fragmentation and resistance to Oedipal drama.