"We Real Cool" first appeared in Gwendolyn Brooks' third published collection of poetry entitled, The Bean Eaters, in which she continues to explore her primary theme, the experiences of Black people in America. Though she had always been writing about her community in South Side Chicago and Black communities across America, The Bean Eaters marks the beginning of a shift in Brooks' approach to the subject; in her earlier work, Brooks was writing more firmly in the context of white America and so-called Western Traditions. She was considered by the literary elite to be a great poet who happened to be Black. But between releasing The Bean Eaters and In the Mecca, Brooks would enter fully into the spirit of the Black Arts Movement and craft a language and tradition of her own images, experimenting more with lean free verse and leaving behind traditional forms. She would eventually argue that her poetry and much of the art coming out of the Black Arts Movement simply could not be fully understood by non-Black people: that this art was not great art that happened to be created by Black artists, but rather, art by and for Black people.
Of the poems included in The Bean Eaters, "We Real Cool" achieved the most fame, likely because of its concision, rhythm, and evocative portrayal of rebellious youth. It has thus been interpreted more generally as a poem about teenage rebellion, but "We Real Cool" isn't about just any teenagers; Brooks most certainly took inspiration from young Black men in South Side Chicago. About the poem's inspiration, she said that she passed by a South Side pool hall one afternoon (while school was very much in session) and spotted a group of high school-aged boys hanging out. The poem explores the performance of masculinity and resistance in young Black men and the deceivingly complex idea of what it means to "be cool."