Following a path established in Robert Warshow’s chapter on “The Gangster as Tragic Hero,” this article attempts to look at connections between the ancient genre of tragedy and contemporary mob movies. On the one hand, there are structural parallels when it comes to plot, which adheres to the formula of decline, brought about by erroneous judgments. On the other hand, mobsters are often portrayed as powerful, ruthless tyrants who retain a kind of Shakespearean grandeur. Using examples from films by Michael Mann, Martin Scorsese, and Ridley Scott, my argument links contemporary American crime drama to the origins of tragedy (as laid out by Aristotle in Poetics) and some canonical examples of the genre, like The Merchant of Venice. Having established this theoretical framework, I shall offer a detailed discussion of Martin Scorsese’s The Departed, one of the most successful mob movies in recent years. In this film, Scorsese toys with the tragic genre both on the level of plot and with regard to his flawed characters, who struggle to overcome guilt and tragic hubris, yet cannot escape their inevitable tragic downfall.