It seems each generation of young people finds new ways to express life's complex emotions and experiences through music. As a favored outlet for self-expression, music also provides future generations with a fascinating historical record. Sound recordings and sheet music of once popular songs offer unique opportunities for students to analyze evidence of historic events, cultural shifts and societal trends from a particular time under study. These primary source formats can prove particularly useful for teachers when addressing complex topics. In this article, the authors offer ideas and strategies for using music from the National Jukebox to teach difficult topics in history. (Contains 1 note.)