Plays in the series include Fences (1987) and The Piano Lesson (1990), each of which won Wilson the Pulitzer Prize for Drama, as well as Ma Rainey's Black Bottom (1984) and Joe Turner's Come and Gone (1988).

Other themes range from the systemic and historical exploitation of African Americans, race relations, identity, migration, and racial discrimination.

"[2] Since Wilson's death, three of his plays have been adapted or re-adapted into films: Fences (2016), Ma Rainey's Black Bottom (2020) and The Piano Lesson (2024).

[5] Wilson's anecdotal history reports that his maternal grandmother walked from North Carolina to Pennsylvania in search of a better life.

Wilson's mother raised the children alone until he was five in a two-room apartment behind a grocery store at 1727 Bedford Avenue; his father was mostly absent from his childhood.

Wilson's mother divorced his father and married David Bedford in the 1950s, and the family moved from the Hill District to the then predominantly White working-class neighborhood of Hazelwood, where they encountered racial hostility; bricks were thrown through a window at their new home.

He dropped out of Gladstone High School in the 10th grade in 1960 after his teacher accused him of plagiarizing a 20-page paper he wrote on Napoleon I of France.

At the age of 16 he began working menial jobs, where he met a wide variety of people on whom some of his later characters were based, such as Sam in The Janitor (1985).

[6] Wilson's extensive use of the Carnegie Library of Pittsburgh resulted in its later awarding him an honorary high school diploma.

She forced him to leave the family home and he enlisted in the United States Army for a three-year stint in 1962, but he was discharged after a year[9] and went back to working various odd jobs as a porter, short-order cook, gardener, and dishwasher.

That same year, he discovered the blues as sung by Bessie Smith, and he bought a stolen typewriter for $10, which he often pawned when money was tight.

[5] He began to write in bars, the local cigar store, and cafes—longhand on table napkins and on yellow notepads, absorbing the voices and characters around him.

[5] Gifted with a talent for catching dialect and accents, Wilson had an "astonishing memory", which he put to full use during his career.

Both the Nation of Islam (NOI) and the Black Power movement spoke to him regarding self-sufficiency, self-defense, and self-determination, and he appreciated the origin myths that Elijah Muhammad supported.

[5] Wilson's first play, Recycling, was performed for audiences in small theaters, schools and public housing community centers for 50 cents a ticket.

"[10] In 1976, Vernell Lillie, who had founded the Kuntu Repertory Theatre at the University of Pittsburgh two years earlier, directed Wilson's The Homecoming.

That same year Wilson saw Athol Fugard's Sizwe Banzi is Dead, staged at the Pittsburgh Public Theater, the first time he attended professionally produced drama.

Wilson had a long association with the Penumbra Theatre Company of St. Paul, which was initially funded by a federal Comprehensive Employment and Training Act (CETA) grant and which premiered some of his plays.

[6] Throughout the 1980s, Wilson wrote the majority of his work including Jitney (1982), Ma Rainey's Black Bottom (1984), Fences (1985), Joe Turner's Come and Gone (1986), and The Piano Lesson (1987).

[16] As a playwright of what is considered the Post–Black Arts Movement, Wilson inherited the spirit of BAM, producing plays that celebrated the history and poetic sensibilities of Black people.

Wilson stated that he was most influenced by "the four Bs": blues music, the Argentine writer and poet Jorge Luis Borges, the playwright Amiri Baraka and the painter Romare Bearden.

He noted: From Borges, those wonderful gaucho stories from which I learned that you can be specific as to a time and place and culture and still have the work resonate with the universal themes of love, honor, duty, betrayal, etc.

[10]Wilson's Pittsburgh Cycle,[18] also often referred to as his Century Cycle,[19] consists of ten plays—nine of which are set in Pittsburgh's Hill District (the other being set in Chicago), an African-American neighborhood that takes on a mythic literary significance like Thomas Hardy's Wessex, William Faulkner's Yoknapatawpha County, or Irish playwright Brian Friel's Ballybeg.

She is reported to be 285 years old in Gem of the Ocean, which takes place in her home at 1839 Wylie Avenue, and 349 in Two Trains Running.

[citation needed] Chicago's Goodman Theatre was the first theater in the world to produce the entire 10-play cycle, in productions which spanned from 1986 to 2007.

[26] TAG – The Actors' Group, in Honolulu, Hawaii, produced all 10 plays in the cycle starting in 2004 with Two Trains Running and culminating in 2015 with Ma Rainey's Black Bottom.

All shows were Hawaii premieres, all were extremely successful at the box office and garnered many local theatre awards for the actors and the organization.

How I Learned explores his days as a struggling young writer in Pittsburgh's Hill District and how the neighborhood and its people inspired his cycle of plays about the African-American experience.

[11] The childhood home of Wilson and his six siblings, at 1727 Bedford Avenue in Pittsburgh, was declared a historic landmark by the State of Pennsylvania on May 30, 2007.

This tribute to Wilson's work is an official contest in many American cities including, as of 2020, Atlanta, Boston, Buffalo, Chicago, Dallas, Greensboro, Los Angeles, New Haven, New York, Norfolk, Pittsburgh, Portland, San Diego, and Seattle.