The aim of this paper was to estimate the effect of obesity on the employment probability for Italian men and women accounting for both observed and unobserved confounding. We use microdata collected by the Italian National Statistical Office for the year 2009 during a multi-scope survey of Italian households. The employment–obesity relationship is estimated after controlling for observed confounding by using probit regression and a propensity score weighting approach. To control for both observed and unobserved confounding (endogeneity), a semiparametric recursive bivariate probit model is employed instead. Our findings suggest that obesity has a significant negative effect on the employment probability and that endogeneity might not be an important issue.