This essay discusses Klein’s concept of “envious spoiling” with two illustrations from Anand Tucker’s extraordinary film, Hilary and Jackie. Tucker’s portrayal of Jacqueline du Pré serves as an invitation for the psychoanalytic viewer to make sense of the following puzzle: Even with her extraordinary musical talent, her worldly acclaim as a cellist and charmed marriage to the celebrated pianist/conductor Daniel Barenboim, Jackie is the sister who suffers from outbursts of uncontained greed, jealousy and envy towards her sister Hilary who is a less talented, less recognized, flautist. Two forms of unconscious envy are suggested: one conveyed through undisguised contempt toward the object (Hilary), the other through a shocking denial of/indifference toward the object’s value. Both modes of enactment serve as release valves for Jackie’s unmetabolized envy. In addition, the cultural landscape of privilege that Jackie’s musical world lives within is recognized and, hopefully, opens the way for acts of internal reckoning.