While Woody Allen is generally considered to be a master of the comic genre he created, his serious films are very important in understanding his role as one of this generation's more influential filmmakers. In this work such Allen films as Annie Hall (1977), Broadway Danny Rose (1984), Crimes and Misdemeanors (1989) and Mighty Aphrodite (1995) are analyzed for the common philosophical themes they share. Gender issues, Allen's love-hate relationship with God, narcissism and moral relativism, and the use of the so-called existential dilemma are among the topics discussed. The extensive research is augmented with a rare interview with Allen.