This paper deals with the Freudian conception of chance and with the way in which this theme is elaborated in the work of writer-director Paul Thomas Anderson. Freud’s interpretation of chance or symptomatic actions, belief in chance and in superstition is illustrated with reference to some small case fragments. P.T. Anderson, in his film Magnolia, also questions the hidden meaning of apparently accidental events in human life. Whereas Freud trips up the illusion of free will by pointing to the determination of our speech and actions by unconscious, powerful mechanisms, Anderson, in contrast, approaches the notion of chance as an astonishing coincidence that should be seized rather than ignored and dismissed as something purely accidental and trivial. It is concluded that both authors make a plea for the not so fortuitous nature of chance and for breaking with repetition by opening our eyes to whatever comes our way by chance.