This essay explores and deconstructs the inner psyche of Anthony Soprano, the protagonist of the TV show ‘The Sopranos’ (1999-2007). This essay puts an explicit focus on the work of Sigmund Freud and Jacques Lacan and their work on subjectivity and the formation of selfhood. The broader aim of this essay is to better understand how a personality is formed, and the ways in which our experiences – even the ones forgotten over time – have a permanent effect on our self-esteem, our behaviour and our response to certain situations. Tony Soprano was chosen for analysis because of the extreme dichotomy between the side of him that wants to be good and the side of him that is demonstrably bad. This essay also discusses whether or not Tony’s inner conflict can be resolved, coming to the conclusion that this is impossible for him. This essay also seeks to avoid an ethical discussion and look objectively at character-forming from a purely psychoanalytic perspective to avoid a discussion of moral relativism, instead hoping to understand the notion of morality as being formed through experience.