In 1959, Wilson was one of 14 African-American students at Central Catholic High School, from which he dropped out after one year. He then attended Connelley Vocational High School, but found the curriculum unchallenging. 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. Wilson hid his decision from his mother because he did not want to disappoint her. 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)

Wilson knew that he wanted to be a writer, but this created tension with his mother, who wanted him to become a lawyer. She forced him to leave the family home and he enlisted in the United States Army for a three-year stint in 1962, but left after one year and went back to working various odd jobs as a porter, short-order cook, gardener, and dishwasher.

Frederick August Kittel Jr. changed his name to August Wilson to honor his mother after his father’s death in 1965. 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. At 20, he decided he was a poet and submitted work to such magazines as Harper’s. 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. He liked to write on cafe napkins because, he said, it freed him up and made him less self-conscious as a writer. He would then gather the notes and type them up at home. Gifted with a talent for catching dialect and accents, Wilson had an “astonishing memory”, which he put to full use during his career. He slowly learned not to censor the language he heard when incorporating it into his work.

In 1968, he co-founded the Black Horizon Theater in the Hill District of Pittsburgh along with his friend Rob Penny. Wilson’s first play, Recycling, was performed for audiences in small theaters, schools and public housing community centers for 50 cents a ticket. Among these early efforts was Jitney, which he revised more than two decades later as part of his 10-play cycle on 20th-century Pittsburgh. He had no directing experience. He recalled: “Someone had looked around and said, ‘Who’s going to be the director?’ I said, ‘I will.’ I said that because I knew my way around the library. So I went to look for a book on how to direct a play. I found one called The Fundamentals of Play Directing and checked it out.”

While the work of August Wilson is not formally recognized within the literary canon of the Black Arts Movement, he was certainly a product of its mission, helping to co-found the Black Horizon Theatre in his hometown of Pittsburgh in 1968. Situated in Pittsburgh’s Hill District, a historically and predominantly Black neighborhood, the Black Horizon Theatre became a cultural hub of Black creativity and community building. As a playwright of what is considered the Post-Black Arts Movement, August Wilson inherited the spirit of BAM, producing plays that celebrated the history and poetic sensibilities of Black people. His iconic Century Cycle successfully tracked and synthesized the experiences of Black America in the 20th Century, using each historical decade, from 1904 to 1997, to document the physical, emotional, mental, and political strivings of Black life in the wake of emancipation.

Malcolm X’s voice influenced Wilson’s life and work (such as The Ground on Which I Stand, 1996). Both the Nation of Islam 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. In 1969 Wilson married Brenda Burton, a Muslim, and converted to Islam. He and Brenda had one daughter, Sakina Ansari-Wilson, and divorced in 1972.

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 Sizwe Banzi is Dead at the Pittsburgh Public Theater, his first professional play. Wilson, Penny, and poet Maisha Baton also started the Kuntu Writers Workshop to bring African-American writers together and to assist them in publication and production. Both organizations are still active.

In 1978 Wilson moved to Saint Paul, Minnesota, at the suggestion of his friend, director Claude Purdy, who helped him secure a job writing educational scripts for the Science Museum of Minnesota. In 1980 he received a fellowship for The Playwrights’ Center in Minneapolis. He quit the Museum in 1981, but continued writing plays. For three years, he was a part-time cook for the Little Brothers of the Poor. Wilson had a long association with the Penumbra Theatre Company of St. Paul, which premiered some of his plays. He wrote Fullerton Street, which has been unproduced and unpublished, in 1980. It follows the Joe Louis/Billy Conn fight in 1940 and the loss of values attendant on the Great Migration to the urban North.

Wilson was married three times. His first marriage was to Brenda Burton from 1969 to 1972. They had one daughter, Sakina Ansari, born 1970. In 1981 he married Judy Oliver, a social worker; they divorced in 1990. He married again in 1994 and was survived by his third wife, costume designer Constanza Romero, whom he met on the set of The Piano Lesson. They had a daughter, Azula Carmen Wilson. Wilson was also survived by siblings Freda Ellis, Linda Jean Kittel, Donna Conley, Barbara Jean Wilson, Edwin Kittel and Richard Kittel.

Although the plays of the cycle are not strictly connected to the degree of a serial story, some characters appear (at various ages) in more than one of the cycle’s plays. Children of characters in earlier plays may appear in later plays. The character most frequently mentioned in the cycle is Aunt Ester, a “washer of souls”. She is reported to be 285 years old in Gem of the Ocean, which takes place in her home at 1839 Wylie Avenue, and 322 in Two Trains Running. She dies in 1985, during the events of King Hedley II. Much of the action of Radio Golf revolves around the plan to demolish and redevelop that house, some years after her death. Aunt Ester is a symbolic and recurring figure that represents the African American struggle. She is “not literally three centuries old but a succession of folk priestesses… [s]he embodies a weighty history of tragedy and triumph”.The plays often include an apparently mentally impaired oracular character (different in each play)—for example, Hedley Sr. in Seven Guitars, Gabriel in Fences, Stool Pigeon in King Hedley II, or Hambone in Two Trains Running.

In 1987, St. Paul’s mayor George Latimer named May 27 “August Wilson Day”. He was honored because he is the only person from Minnesota to win a Pulitzer Prize.

In 1990 Wilson left St. Paul after getting divorced and moved to Seattle. There he developed a relationship with Seattle Repertory Theatre, which became the only theater in the country to produce his entire 10-play cycle and his one-man show How I Learned What I Learned.

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. The Black Rep in St. Louis and the Anthony Bean Community Theater in New Orleans have also presented the complete cycle.

Two years before his death in 2005, August Wilson wrote and performed an unpublished one-man play entitled How I Learned What I Learned about the power of art and the power of possibility. This was produced at New York’s Signature Theatre and directed by Todd Kreidler, Wilson’s friend and protégé. 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.

Wilson reported that he had been diagnosed with liver cancer in June 2005 and been given three to five months to live. He died on October 2, 2005, at Swedish Medical Center in Seattle, and was interred at Greenwood Cemetery, Pittsburgh, on October 8, 2005, aged 60.

On October 16, 2005, fourteen days after Wilson’s death, the Virginia Theatre in New York City’s Broadway Theater District was renamed the August Wilson Theatre. It is the first Broadway theatre to bear the name of an African-American. The theatre has run many shows, one of the most famous being Jersey Boys and now Mean Girls.

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. On February 26, 2008, Pittsburgh City Council placed the house on the List of City of Pittsburgh historic designations. On April 30, 2013, the August Wilson House was added to the National Register of Historic Places.

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. Two of the Goodman’s productions—Seven Guitars and Gem of the Ocean—were world premieres. Israel Hicks produced the entire 10-play cycle from 1990 to 2009 for the Denver Center Theatre Company. Geva Theatre Center produced all 10 plays in decade order from 2007 to 2011 as August Wilson’s American Century. The Huntington Theatre Company of Boston has produced all 10 plays, finishing in 2012. During Wilson’s life he worked closely with The Huntington to produce the later plays. Pittsburgh Public Theater was the first theater company in Pittsburgh to produce the entire Century Cycle, including the world premiere of King Hedley II to open the O’Reilly Theater in Downtown Pittsburgh.

In September 2016, an existing community park near his childhood home was renovated and renamed August Wilson Park.

In 2020, the University Library System at the University of Pittsburgh acquired Wilson’s literary papers and materials to establish the August Wilson Archive.