Nighttime driving cannot be accomplished without vehicle headlighting. A growing body of evidence demonstrates the role of lighting on visual performance and in turn on nightttime driving safety in terms of crashes. Indirect impacts of lighting via comfort or other factors are less well understood, however. A two-part field study using real-world drivers of an instrumented vehicle was conducted to assess the potential role of oncoming headlight glare as a factor in driving behaviors that might be related to increased crash risks. In the first part of the study, drivers' behaviors when navigating through roadway intersections having different levels of crash risk were recorded in order to identify responses that were correlated with the risk level. In the second part, drivers were exposed to different levels of glare from oncoming headlights; several of the same risk-related behaviors identified in the first part of the study were exhibited. The results suggest that discomfort from headlight glare, including effects from vertical misaim, could be correlated with increased nighttime crash risk while driving.