This paper investigates the role of pain dynamics in subsequently affecting dynamics in self-reported work disability and the dynamics of employment patterns of older workers in the US. Not only is pain prevalence quite high, there also are many transitions in and out of pain at these ages. We investigate pain and its relationship to health (work disability) and work in a dynamic panel data model, using six biennial waves from the Health and Retirement Study. We find that the dynamics of the presence of pain are central to understanding the dynamics of self-reported work disability and through this pathway, pain dynamics are also a significant factor in the dynamic patterns of employment.