In this essay I study the movie, Skyfall, from the point of view of the need for the hero to appropriate shadow qualities, notably, psychopathic qualities, to consciousness. I particularly examine James Bond with respect to these attributes in relationship to his nemesis, Raoul Silve, aka Tiego Roderick. I argue that the former is a genuine hero, although he has a trickster-puer shadow that remains until the end, whereas the latter is a trickster psychopathic destroyer. I also point out that with his new boss, Gareth Mallory, who replaces M, after she dies at the end of the movie, there may be an opportunity for James Bond to leave the trickster cycle altogether and to fully embrace the hero dynamic. In the Epilogue, I specifically show how individuals today can be touched by the message of the movie and to take it further for the sake of individuation and bringing in a new world. There is a need to appropriate psychopathic shadow traits to gain the strength to overcome obstacles and resistances for this eventuality.