How do older men’s masculine ideals affect their health? Are masculine activities involved in this relationship? Masculine identity upholds beliefs about masculine enactment. These beliefs can be detrimental to men and can lead to behaviors that can put undue stress on them. We examine how masculine ideals are associated with health and depressive symptomatology in older men. We used 2011 data from the Wisconsin Longitudinal Study ( n = 2,594) to investigate how masculine ideals inform older men’s health and how participation in masculine activities might shape these outcomes. Findings from this study illustrate that traditional masculine ideals are associated with worse self-rated health (SRH), greater chronic illness, and depressive symptomatology. For masculine activities, doing repairs and car maintenance was associated with less chronic illness and depression. Belonging to a senior men’s group was associated with worse SRH, greater chronic illness, and greater depression. Therefore, older men’s greater endorsement of traditional masculine ideals was generally associated with worse health, though certain masculine activities affected this relationship. We posit that more gender-equitable beliefs may be useful for improving the “men’s health gap.”