This chapter discusses the poets associated with the so-called “Middle Generation,” a transitional group of writers who were younger than the modernists but older than the poets of the New American poetry discussed in Chapters 1–4. It addresses how the poets of this cohort struggled with the long shadow of their modernist predecessors and addresses their struggles with alcoholism, personal crises, and mental illness. The chapter charts their move away from the New Critical formalist mode that reigned at mid-century toward a looser, more personal mode, which eventually gave rise to Confessional poetry. Focusing especially on Elizabeth Bishop (who distanced herself from Confessionalism), Robert Lowell, John Berryman, Sylvia Plath, and Anne Sexton, this chapter discusses the major stylistic and thematic features of Confessionalism, controversies surrounding this movement, and its profound influence on contemporary poetry.