Can ancient prayers and modern poetry illuminate each other, revealing shared human struggles with mortality and meaning? Through comparative analysis of Jewish liturgical poetry (t'fillah) and contemporary secular verse, profound connections emerge between seemingly disparate literary traditions. A detailed examination of Robinson Jeffers' "To the Stone-Cutters" alongside the memorial prayer "El Malei Rachamim" reveals how both texts grapple with death, remembrance, and humanity's resistance to oblivion - though through markedly different lenses. While Jeffers portrays monument-building as a futile stand against mortality, the Jewish prayer affirms divine power to eternally preserve souls. This methodology of using contemporary poems as interpretive mirrors for understanding siddur prayers offers a fresh approach to iyyun t'fillah (meditative prayer study). The analysis demonstrates how both genres create meaning through their treatment of impermanence and memory, despite their divergent theological frameworks. Beyond serving Jewish communities seeking deeper liturgical engagement, this comparative approach benefits anyone exploring the intersection of literary and spiritual traditions, showing how ancient religious texts and modern poetry can mutually illuminate fundamental human experiences of loss, remembrance, and hope.