The gifted and rebellious writer Claude McKay grew up in the British West Indies and then moved to the United States. As he traveled from Jamaica to South Carolina to Harlem, then to Europe and Africa, he embraced various causes and political ideologies that made their way into his prose and poetry. As a black in a British colony, he had been confined to British culture and identity. In the United States he found racial oppression. His struggle for self-definition and self-determination was manifest in his writings and laid the foundation for the Harlem Renaissance and negritude movements. This study explores the life and works of Claude McKay, framed within his cross-cultural experiences. As it traces his life, it also considers how a subject dwells in limbo between native and adopted cultures, and how this influenced McKay’s writing. Critics in the United States tend to focus on McKay’s American productions, such as his poetry and novels like Home to Harlem, while critics in the Caribbean focus on his works there: novels like Banana Bottom and dialect poetry. This work examines all the facets of this influential early 20th century author, a man trying to solve the problem of his own identity in a world determined to marginalize him.