This chapter focuses on the career of Jean Toomer. It looks first at Toomer’s Washington upbringing among the black bourgeoisie, his course of reading in modern literature and the attraction for Toomer of the Greenwich Village literary world he associated with an “aristocracy of culture.” It then examines the way Toomer, following the advice of his friend Waldo Frank, capitalized on his African American identity and experience in the South in writing his first book Cane, which he retrospectively thought of as his “passport” into the literary world. The chapter goes on to demonstrate the extent to which Cane became a burden for Toomer, as it came to define him as a “Negro writer” despite the more ambitious, post-racial works he was writing, none of which could get published. It focuses finally on the reasons why African American anthologists and critics needed to claim Cane for African American literature – in good part, the chapter argues, because it showcased the race’s capacity for modernist experimentation. And it deals finally with Toomer’s reluctant agreement to be anthologized as an African American writer, as this ensured that his writing would endure.