This dissertation examines the journey of the hero away from society as a universal theme of initiation, as is exemplified in literary works that represent polar extremes of culture. Given the generally accepted critical view that a young man\u27s apprenticeship in life through confrontation with the world towards an assimilation of himself into society is the dominant theme of initiation fiction, this study demonstrates that the hero\u27s voyage out, his rejection of society for the sake of integrity, is a significant reversal of, and hence a compelling alternative to, the socially oriented pattern of the Bildungsroman within the context of initiation literature.^ The study observes, on the one hand, distinctions between Chinese and Western cultures as they are reflected in the writers\u27 different perceptions of conflicts between innocence and experience and between the ideal and reality. It investigates, on the other hand, the parallels between the American separatist tendency and the Taoist-Buddhist philosophy of renunciation, in contrast with the social orientation of both European culture and Confucianism. The study shows that the kind of initiation narrative in which the tension between the hero and the world does not evolve towards a compromise often originates from the author\u27s critical response to as well as his equivocal attitude towards the contending forces within the culture.^ The study also argues that while highly responsive to their own cultures, Mark Twain, Henry James, and Cao Xueqin, as truly great artists, penetrate beyond culture to the commonest as well as deepest human experience; they are, therefore, mutually reflective and shed light on one another. Combining the cross-cultural perspective with a formalist approach, this study examines recurrent metaphors, structural patterns, and character types in the works of the three authors as indications of a shared thematic interest. Last but not least, the study discusses the convergence of the Twainian vernacular style and dream vision with the Jamesian social sensibility and psychological realism in the Chinese novelist Cao Xueqin\u27s masterpiece A Dream of Red Mansions.