This paper attempts to solve the problem of postmodern tragedy by examining two films by British director Michael Winterbottom, Tristram Shandy: a Cock and Bull Story, and 24 Hour Party People. Actually, I am not certain that the notion of postmodern tragedy is problematic as much as it is non-traditional in terms of classical critical definitions of tragedy. The films suggest that the postmodern protagonist faces the same trials as the protagonist from any other era, but responds to them differently, if at all. My thesis states that the protagonist‘s failure to respond adequately to the consequences of his choices, indeed, his failure to learn from his own repeated failures, is the basis for the tragedy presented in the films, as well as the basis for tragedy in the postmodern era. Certainly choice has always been key regarding the tragic fall of characters, from Oedipus to Willy Loman, and beyond. The particular circumstances of the films in question, however, suggest that the fall is not here the ultimate tragedy. Rather, these films clearly portray their respective protagonists as incapable of falling, in the tragic sense, because, whether consciously or unconsciously, they tend to reach not for greatness, but for failure, and as each failure mounts, they descend a little lower, as though the true glory of endeavor is to dig as deep a hole as possible by mounting failure on top of failure. In a sense, as the paper makes clear, the protagonists of these films attempt to define success by failure, or, to use a mathematical metaphor, they attempt to define themselves by their proximity to zero.