This chapter examines Caribbean writing of the 1950s–1960s in relation to modernism as a concept, movement, and literary practice. Based on writing by Caribbean intellectuals, including C. L. R. James, George Lamming, Wilson Harris, and Édouard Glissant, and building on work by critics Simon Gikandi, Charles Pollard, Mary Lou Emery, Maria Cristina Fumagali, and others, it identifies a project of questioning modernism that challenged Eurocentric notions of Enlightenment modernity while contributing to modernist aesthetics. Further, it suggests that Caribbean writers of that period anticipated and currently inspire revisions of mainstream modernist studies. Critical reassessments of the Windrush generation, including feminist critiques of canon formation (J. Dillon Brown, Peter Kalliney, Faith Smith, Leah Rosenberg, and Alison Donnell), help support the essay’s argument for the importance of earlier decades of Caribbean modernism along with translinguistic philosophical and artistic influences. Specific readings focus on interactions among literary and visual arts – especially in the work of Lamming, Harris, Kamau Brathwaite, Roger Mais, and Aubrey Williams. In the writing of Harris, Brathwaite, and Jean Rhys, the essay locates ‘tropes of brokenness’ as ground for new concepts of the individual, new portrayals of vision, and a Caribbean modernist poetics based on creolized and indigenous arts.