We investigate the effects of light cone caustics on the propagation of linear scalar fields in generic four-dimensional spacetimes. In particular, we analyze the singular structure of relevant Green functions. As expected from general theorems, Green functions associated with wave equations are globally singular along a large class of null geodesics. Despite this, the "nature" of the singularity on a given geodesic does not necessarily remain fixed. It can change character on encountering caustics of the light cone. These changes are studied by first deriving global Green functions for scalar fields propagating on smooth plane wave spacetimes. We then use Penrose limits to argue that there is a sense in which the "leading order singular be...