In this chapter we investigate various representations of masculinity in the HBO TV series The Sopranos (1999-2007) through a discussion and analysis of the portraits of fathers and sons. Our analysis is based on theories grounded in gender and class, but also psychoanalytical theory, a framework that the series draws on to considerable extent. The award winning series depicts the difficulties and limitations of adapting to and combining different gender regimes. One of the major sources of conflict and psychological distress is Mafioso Tony Soprano's attempts to negotiate traditional working-class conceptions of masculinity and post-modern, middle class notions of father- and manhood. In this chapter we will use a multifold theoretical methodology where masculinity studies, psychoanalysis , class, sexuality and vaious forms of Bourdieu's capital are important means to approach and comprehend the never-ending, on-going conflicts and negotiation in father-son relationships, and to see the reasons why the fathers and sons cannot truly meet and understand each other. The analysis of the series comes to the conclusion that due to the fact that their different social, cultural, and economic capitals differ so much, the father and son is doomed to fail; they cannot "get alony"