In this longitudinal study, we compared family stories told by 32 Canadian adolescents at ages 16 and 20 about how parents and grandparents had taught them values. Relations to parents' and children's levels of generativity were also examined. Adolescents' stories of grandparent value teaching were less readily recalled and less interactive in their content compared with stories about parents. Stories of value teaching by more generative parents were more likely to involve specific episodes, to be more interactive, to be more likely to emphasize caring content, and to be less likely to have their message rejected by the teens. Similarly, when parents were more generative, adolescents' stories about grandparents' value teaching were also more likely to involve specific and interactive episodes. Finally, stories told about parents and grandparents that were more positive on these dimensions predicted higher generative concern scores for the adolescents themselves, measured subsequently at age 24. Adolescents' stories about parent and grandparent socialization in more generative family contexts thus have features that suggest a more compelling process of intergenerational value transmission.