The vulnerability model states that low self-esteem functions as a predictor for the development of depressive symptoms whereas the scar model assumes that these symptoms leave scars in individuals resulting in lower self-esteem. Both models have received empirical support, however, they have only been tested within individuals and not across generations (i.e., between family members). Thus, we tested the scope of these competing models by (a) investigating whether the effects hold from adolescence to middle adulthood (long-term vulnerability and scar effects), (b) whether the effects hold across generations (intergenerational vulnerability and scar effects), and (c) whether intergenerational effects are mediated by parental self-esteem and depressive symptoms and parent–child discord. We used longitudinal data from adolescence to middle adulthood (N = 1,359) and from Generation 1 adolescents (G1) to Generation 2 adolescents (G2) (N = 572 parent–child pairs). Results from latent cross-lagged regression analyses demonstrated that both adolescent self-esteem and depressive symptoms were prospectively related to adult self-esteem and depressive symptoms 3 decades later. That is, both the vulnerability and scar models are valid over decades with stronger effects for the vulnerability model. Across generations, we found a substantial direct transmission effect from G1 to G2 adolescent depressive symptoms but no evidence for the proposed intergenerational vulnerability and scar effect or for any of the proposed mediating mechanisms.