This thesis analyzes composer and lyricist Stephen Sondheim’s 1987 work, Into the Woods. In doing so, this study examines Stephen Sondheim’s political and cultural awareness in the 1980s. Through lyrical and musical analysis, this study connects Into the Woods to two critical issues of its time: the HIV AIDS epidemic of the late 1970s to 1980s, and the normalization of sexual violence. While many have asserted that these connections may be inconsistent with the writer's intentions, this study aims to explore Into the Woods as a work of its specific cultural and political period. This analysis indicates how Sondheim intertwines political and cultural themes in his work. To accomplish this, he utilizes cultural commentaries/connections, metaphors for current events, and thematic motifs. Sondheim's lyrics' syntax, vocabulary, and tone evince the abovementioned themes. Musically, Sondheim utilizes melodic motifs, changes in underlying harmony, and unique text settings to subtly portray political and cultural themes. Considering political and cultural themes in Sondheim's works revitalizes and brings intrigue to his works and his legacy. While this study examines one of Stephen Sondheim's works, recommendations for further analysis is included.