In this essay the post-classical, legendary, and chivalric sagas (and their rímur counterparts) are explored for their mutual interdependence and generic variety. In addition, two late medieval rímur poems, Völsungs rímur and Skógar-krists rímur, are examined in light of Tolkien’s two essays in order to identify how these two poems provide valuable philological insights into late medieval Icelandic literature. Overall, the two rímur exemplify the development of legendary sagas and fairy tales into the late medieval period.