Although Berryman published poems and achieved recognition early, his first major work was Homage to Mistress Bradstreet in 1956. However, it was the collection of Dream Songs that gathered him the most admiration. The first volume, entitled 77 Dream Songs, was published in 1964 and won the Pulitzer Prize for poetry. The second volume of Dream Songs, entitled His Toy, His Dream, His Rest, appeared in 1968. The two volumes of Dream Songs were published together as The Dream Songs in 1969.
The Dream Songs are seventeen line poems in three stanzas. Each individual poem is lyric and organized around an emotion provoked by an everyday event. The tone of the poems is less surreal than associational or intoxicated, and yet each is carefully constructed, with a great deal of control of both wording and thought hidden beneath an apparent randomness. The poems appear to be nearly diary entries, and yet they are neither trivial nor occasional. The principal character of the song cycle is Henry, who is both the narrator of the poems and referred to by the narrator in the poems. Henry often speaks to himself in the guise of Mr. Bones, a blackface minstrel show version of himself. Because readers assumed that Henry, the narrator, and Mr. Bones were all the poet speaking directly of himself, Berryman's poetry was considered part of the Confessional Poetry movement. Berryman, however, scorned the idea that he was a Confessional poet.
Berryman's biography is dominated by suicide. In 1924, when the poet was ten, his father, John Smith, a banker in Florida, shot himself. The poet was the first person to discover the body. After his father's death, the poet's mother remarried, and thus he came to his new surname of Berryman. The vision of his father's suicide haunted John Berryman's poetic imagination, and the subject is addressed indirectly in the Dream Songs several times and directly once, where the poet wishes that he could kill the corpse of his father. Berryman was an alcoholic, and friends reported that even as a student at Columbia University he was two different people when drinking and sober. As a mature poet, Berryman's alcoholism and depression interfered with his ability to give readings, to speak in public, and to work appropriately. In 1972, Berryman's depression led him to follow the example of his father and to kill himself by jumping from a bridge in Minneapolis, Minnesota.