© The Author(s) 2019. A growing body of work identifies distinct health lifestyles among children, adolescents, and young adults and documents important social correlates. This study contributes to that line of research by identifying the health lifestyles of U.S. adults entering late middle age, assessing structural predictors of membership in different health lifestyles in this understudied age-group, and examining net associations between health lifestyles, chronic conditions, and physical health. The data come from the National Longitudinal Survey of Youth 1979 50+ Health Module. The analysis is based on respondents who answered the 50+ Health Module in 2008, 2010, 2012, or 2014 (N = 7,234). The results confirm similar relationships between health lifestyles and structural factors like class, gender, and race that prior studies observe and also reveal a unique pattern of associations between health lifestyle and health status because of diagnosed conditions that impact health behaviors in adulthood.