Leonard Bernstein, one of the most prominent American composers and conductors of the twentieth century, has a repertoire that reflects the American political and cultural environment, from racial, urban, multicultural issues to the relationship with faith in turbulent times. In addition, Bernstein was an exceptional teacher, particularly to a large part of Americans through the television programs he hosted where he introduced a generation to the beauty and complexity of classical music. In this article, we seek to look at two vertices of Leonard Bernstein's activity—composition and education—through the prism of Cultural Literacy. Our goal is, through an extensive literature review, to understand how Leonard Bernstein promoted cultural literacy skills both through his compositions and through his lessons, namely in television programs.