How are one’s own education, father’s education, and especially the combination of the two, related to self‐assessed health across European societies? In this study, we test hypotheses about differences in self‐assessed health between 16 post‐socialist countries in Central and Eastern Europe and 17 Western European countries. We find substantial cross‐national variation in the (relative) importance of own and father’s education for self‐assessed health. Over 65 per cent of this cross‐national variation is accounted for by the East–West divide. This simple dichotomy explains cross‐national differences better than gross domestic product or income inequality. An individual’s father’s education is more important, both in absolute and relative terms, for self‐assessed heath in Eastern Europe than in Western Europe. Intergenerational mobility moderates the relative effects of one’s own and one’s father’s education. In Eastern Europe the relative importance of one’s father’s education is greater than it is in Western Europe – particularly for those who are downwardly mobile and have a father with tertiary education. The results are sometimes contradictory to initial expectations; the theoretical implications are discussed.