This article investigates how Percy Bysshe Shelley (1792-1822) embodies the diverse aspects of his internal crisis in despairing lyrics based on severe physical illness and tragic family occasions of 1817-8. It argues that the interlinking poems and prose written over these periods reveal the author’s agonizing response to the inevitable facets of the world and his life, which involves the recurrent motifs of mortality, ruination, and despondency. The paper furthers how he confronts this transitory necessity with an awareness of hope and love. The writer intertwines these positive reactions with the speaker’s paradoxical experiences of irony and dilemma when facing the ongoing affliction imposed by uncertainly and instability regarding the anticipation for a liberation from such afflictive moments. Shelley’s poems to depict despondency, however, embed the dynamic progress of the speaker’s mind, which associates with his resilient quest for spiritual freedom unyielding to the physical and internal trapment. This adherence of liberty prefigures the works of his final year 1822, especially A Defence of Poetry where he epitomizes the nature of imagination as a substantial power to bring ultimate freedom and mutual love to the gloom of the present life.