Kenneth Lonergan's three films- (2000), (2011), and (2016)-are rife with philosophical complexities. They challenge simple philosophical approaches to central issues of human behaviour. In particular, they ask questions about how to cope with suffering that one cannot overcome, the role that self- deception plays in people's lives and how to think about characters who do not embody simplistic moral ideas of virtue and vice. By philosophically engaging with these themes as they unfold in Lonergan's films, we are then able to formulate a more nuanced answer to the questions they pose. will draw from Lonergan's films and plays, along with the philosophical literature on the topics that they explore. The rich history of philosophical reflection surrounding these areas enables the reader to determine how the themes central to Lonergan's work have combined to create a rich cinematic oeuvre.