"There's a time when what you're creating and the environment you're creating it in come together," painter Grace Hartigan once said. She was talking specifically about a certain group of poets and painters living in New York City in the 1950s and 1960s. Known famously now as the "New York School," the group included poets John Ashbery, Kenneth Koch, Barbara Guest, Frank O'Hara, and James Schuyler; Abstract Expressionist painters Willem de Kooning, Jackson Pollock, Mark Rothko, and Robert Motherwell; and "second-generation" New York School painters Hartigan, Jane Freilicher, Michael Goldberg, and Larry Rivers, who were influenced by Abstract Expressionism but also reacting against it by creating works that were hybrids of "pure" abstraction and traditional representative painting.

Ashbery describes the relationship between the New York School poets and painters as almost accidental:

My arrival in New York coincided with the cresting of the "heroic" period of Abstract Expressionism, as it was later to be known, and somehow we all seemed to benefit from this strong moment even if we paid little attention to it and seemed to be going our separate ways. We were in awe of de Kooning, Pollock, Rothko and Motherwell and not too sure of exactly what they were doing.

Although the group of friends shared relatively few aesthetic similarities, most were drawn to collaborations across poetry and art. Many of the poets had their first volumes published by John Bernard Myers under the Tibor de Nagy Gallery imprint, a press that also published editions of poems accompanied by artwork from Rivers, Freilicher, or Hartigan. The New York School poets and painters shared a social scene and a community, appearing frequently in each other's work and letters, reading together, working on literary journals, and becoming champions of each other’s poetry and artwork. Collaborations and responses between the artists and poets were so numerous that they are almost impossible to catalog. Hartigan created a group of notable silkscreens called the "Salute" series, which are responses to a series of Schuyler poems by the same name. The short poem in the series, entitled "Flashes," begins:

Dark day
swarming west
the Chrysler Building
silver, soluble
not a hole
a depth

Hartigan's illustration of this poem, titled "On a Tar Roof," depicts not only the recognizable shape of the Chrysler Building, but also the shape of the poem. The curve of the black lines in Hartigan's painting echoes the length and jaggedness of the lines in Schuyler's poem, as if syntax and line breaks had an artistic equivalent.

Guest, O’Hara, Schuyler and Ashbery all wrote reviews for ARTnews, one of the most influential art magazines of the 1960s. Ashbery was executive editor for nine years. Schuyler and O’Hara both worked at the Museum of Modern Art. Ashbery described O’Hara as the poet who was able to "cobble everything together" and strengthen and describe the relationships between the worlds of poetry and art. O’Hara’s poetry, because of its familiarity of language and reference and autobiographical nature, contains references to Hartigan, Freilicher, Ashbery, Koch, Rivers, Goldberg, and Guest. O’Hara describes the New York School in "Larry Rivers: A Memoir":

There was a great respect for anyone who did anything marvelous: when Larry introduced me to de Kooning, I nearly got sick, as I almost did when I met Auden; if Jackson Pollock tore the door off the men’s room at the Cedar it was something he just did and was interesting, not an annoyance. You couldn’t see into it anyway, and besides there was then a sense of genius.

When critics speak of a second-generation New York School poetry, they are referring to poets such as Joe Brainard, Alice Notley, Ted Berrigan, Ann Waldman, Dean Young, and Bernadette Mayer. Like their predecessors, these poets have a variety of styles and forms only loosely held together by an imagistic intensity and a tendency towards humor and familiarity. While some speak of a "third generation" and after, influence of the New York School is now so pervasive that such a term has become almost meaningless.

O’Hara had perhaps the best (and most simple) explanation for the collaborations of the New York School—a preference for the same bars:

We were all in our early twenties. John Ashbery, Barbara Guest, Kenneth Koch, and I, being poets, divided our time between the literary bar, the San Remo, and the artists’ bar, the Cedar Tavern. In the San Remo we argued and gossipped: in the Cedar we often wrote poems while listening to the painters argue and gossip. So far as I know nobody painted in the San Remo while they listened to the writers argue and gossip.