We study the relationship between macroeconomic conditions and self-reported health in a large sample of Italian individuals, focusing on the mediating role played by health behaviors (smoking, alcohol consumption, physical activity, eating habits) and economic stress. Our findings indicate that, overall, higher local unemployment is negatively related to individuals’ health conditions. A one percentage point increase in the province-level unemployment rate is associated with a significant increase in the probability of experiencing diabetes (0.03 percentage points), infarction (0.01), ulcer (0.06), cirrhosis (0.01) and nervous disorders (0.07), with a time lag that differs across individual health conditions. Employment status and educational level play a significant role as moderators of these relationships. Eating habits, in addition to economic stress, play a key role as mediators, by enhancing the negative relationship between macroeconomic conditions and health outcomes, while physical exercise is found to play a dampening role.