This thesis provides an alternative way of reading The Picture of Dorian Gray, and rethinks the role of Lord Henry Wotton in novel. My thesis is divided into five chapters. An introductory Chapter provides an overview to Lord Henry Wotton with an evaluation of established readings of The Picture of Dorian Gray. Chapter I is the analysis on Lord Henry Wotton’s interpretation and understanding of pleasure, which dominates his behavior throughout the novel. In Chapter II, I explain how Lord Henry Wotton develops his intimate relationship with Dorian Gray, and how he experiences various pleasures from talking to the younger man. Chapter III explores the gradual downfall of Lord Henry Wotton, for in the later chapters in the novel the young man changes and takes away the pleasure that Wotton used to enjoy. Finally, in the last chapter, I deliver an in-depth discussion on Wotton’s tragic treatment within the narrative, for I believe he receives an ending that is even more sorrowful than Dorian Gray’s.