To better understand the health status of men in the United States, this study aimed to assess the association of hardship on the presence of and pain severity among men 50 years of age and older. Cross-sectional multivariate logistic regression analyses were conducted using the 2010 wave of the Health and Retirement Study (N = 3,174) to assess the association between four hardship indicators and the presence of pain and pain severity among this sample of older men. Results suggest that the association between the presence of pain and hardship was statistically significant across all four indicators: ongoing financial hardship (CI [1.05, 1.63], p <.05), difficulty paying bills (CI [1.42, 3.02], p <.001), food insecurity (CI [1.46, 3.15], p <.001), and not taking medication due to cost (CI [1.06, 1.66], p <.05), even after adjusting for all demographic factors. The associations between pain severity and ongoing financial strain (CI [1.23, 2.83], p <.01) and difficulty paying bills (CI [1.02, 3.18], p <.05) were statistically significant. Results also indicate that education was a buffer at all levels. In addition, the interactive effect of hardship and Medicare insurance coverage on pain severity was significant only for ongoing financial strain (CI [1.74, 14.33], p >.001) and difficulty paying bills (CI [1.26, 7.05], p <.05). The evidence is clear that each hardship indicators is associated with the presence of pain and across some of the indicators in pain severity among men aged 50 and older. In addition, these findings stress the importance that Medicare insurance plays in acting as a buffer to alleviate some of the hardships experienced by older men. These findings also highlight the association between the presence of pain and pain severity for the overall quality of life, health outcomes, and financial position of men in later life. © The Author(s) 2018.