The first essay of this dissertation investigates the effect of macroeconomic fluctuations at school-leaving on men's health at age 40. I use macroeconomic fluctuations in the U.S. between 1976 and 1992 as a quasi-experiment to identify persistent health effects. I proxy macroeconomic fluctuations with the state unemployment rate. I draw data from the National Longitudinal Survey of Youth 1979 Cohort (NLSY79) Age 40 Health supplement. I examine three measures of health: physical and mental functioning and depressive symptoms. I find that men who leave school when the state unemployment rate is high have worse physical and mental health functioning, and more depressive symptoms at age 40 than men who left school when the state unemployment rate was low. The second essay tests the persistent effect of macroeconomic fluctuations at leaving school on three markers of health behavior: smoking, binge drinking, and obesity. Data are drawn from the NLSY79. I exploit macroeconomic fluctuations at school leaving between 1976 and 1995 to identify effects. I proxy macroeconomic fluctuations with the state unemployment rate. I find that leaving school when the state unemployment rate is high leads to an increase in the probability of binge drinking and a decrease in the probability of obesity in middle age. Health behavior marker effects are concentrated among college educated men. The third essay contributes to the literature on the labor market consequences of unhealthy behaviors by examining a previously underappreciated consequence of the rise in obesity in the U.S.: challenges for military recruitment. Specifically, this essay estimates the percent of the U.S. military-age population that exceeds the Army's current active duty enlistment standards for weight-for-height and percent body fat, using data from the full series of National Health and Nutrition Examination Surveys (1959-2008). This essay documents a substantial increase in the number and percent of military-age civilians who are ineligible to serve in the Army because they are overweight, finds disparities across race and education in exceeding the standards, and estimates the implications for military recruitment of future changes in the prevalence of obesity.