Max Weber is noted for his analysis of the `specific and peculiar rationalism' of western culture. However, his diagnosis of a life disenchanted by reason draws attention to his lesser known formulations of the problem of theodicy - the problem of reconciling pain and misfortune with moral expectations of the world. Weber suggests that cultural responses to this problem change with the increasingly secular rationalization of life. The present paper traces this development from the cultural representation of pain as the embodiment of moral strife in the early modern novel to contemporary images of pain and suffering in medicine, the mass media and film. The comparison suggests that late modernity is confronted by an `inverse' problem of theodicy, in which representations of pain and suffering are disassociated from ethical and political contexts and the quest for meaning within a human frame.