This chapter explores the enduring motif of “The Monk and the Bird” —where a monk is entranced by a bird’s song and loses all sense of time—tracing its evolution from medieval Christian exempla and European folklore to literary adaptations by Henry Wadsworth Longfellow, Geoffrey Bache Smith, and J.R.R. Tolkien. The chapter argues that Smith’s poem Legend and Tolkien’s works—including The Lay of Leithian, The Tale of Tinúviel, and “The Death of Saint Brendan” (“Imram”)—draw directly from Longfellow’s “Monk Felix” episode in his long narrative poem, The Golden Legend (1851), sharing its narrative structures, poetic form, and thematic elements such as disjunctions of time and the Otherworld. Smith and Tolkien also introduce innovations, blending Christian and Celtic traditions, and incorporating motifs of death and overseas paradises. Through close textual analysis, the chapter reveals a rich intertextual dialogue among these authors, suggesting both direct influence and collaborative literary evolution. Ultimately, it highlights how a medieval motif was transformed into a powerful symbol of timelessness, enchantment, and spiritual transcendence in early twentieth-century mythopoeic literature.