Rosenak has shown that contemporary Jewish education must negotiate the tension between relevance and authenticity. For those who embrace authenticity as a goal, education is often mediated through heroes--who are ideal cultural types. Such education is hampered by the diminution of heroes in contemporary culture: The hero has been replaced by the role model, and the aspiration to be like the hero has been replaced by individualism. This article explores the idea of heroes in education both in the philosophic literature (Taylor, McIntyre, Rosenak) and in various aspects of Jewish education in the United States, including a look at wider American Jewish culture in this regard. A brief comparison to Israeli Jewish education is also included, where similar tensions and dilemmas are found.