Robert Schumann's Frauenliebe und -leben and Dominick Argento's From the Diary of Virginia Woolf are two song cycles that enjoy frequent performances. Argento modeled the large-scale form and dramatic concept of his own work after Schumann's cycle: eight songs depicting chronological moments from a woman's life feature a return in the last song to thematic material from the first song. With this comparative analysis of these two song cycles, the author argues that the two works have more in common than a broad schematic design. The song cycles are linked on many important musical and dramatic levels. Due to the preponderance in both Frauenliebe und -leben and From the Diary of Virginia Woolf of strophic- and rondo-like writing, there is an obsessive quality that becomes apparent, though the object of obsession is different in each of the cycles. In the Schumann cycle, it is the patriarchal view that a woman's obsession should be her husband, family, and home life. While in the Argento cycle, it is an artist's obsession with her writing and her own thoughts on the complexity of life that directs the listener. This document examines the similarities and differences between the two song cycles, primarily through musical means but taking into account text and drama, as well. Aspects such as text, concept, large- and small-scale formal structures, recurring motivic material, accompaniment, character and mood, and performance considerations all bear some degree of similarity between the two cycles and are examined here to show why they effectively complement one another in performance. A thorough understanding of both works and how they relate to each other also helps to inform the artists' performance.