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."