In 1962, Wilson moved to
Greenwich Village in New York City. He worked in odd jobs, such as a temporary typist, a reservations clerk at
Americana Hotel, at the complaint desk of a furniture store, and at a dishwashing job where a co-worker incorrectly called him "Lance". After that, Wilson's friends all called him by that name. Wilson first encountered the
Caffe Cino when he went to see
Eugène Ionesco's
The Lesson. The experience left him thinking that theatre "could be both dangerous and funny in that way at the same time". Cino encouraged Wilson to submit a play to the Cino. In Cino, Wilson found a mentor who would not only critique his plays, but also stage them.
The Madness of Lady Bright premiered at Caffe Cino in May 1964. The play concerns "Lady" Bright, who is a forty-year-old "screaming preening queen". On a sultry summer day in the 1960s, while in his apartment on the Upper West Side of Manhattan, "Lady" Bright slowly loses his mind. It is a complex and comic tragedy of striking originality, and one of Wilson's most notable and finest works. At its heart, the work is a penetrating study of loneliness and isolation. It was one of off-off-Broadway's first significant successes, running for over 200 performances.
The Madness of Lady Bright set a record as the longest-running play at Caffe Cino. In 1965, Wilson began writing plays for
Ellen Stewart's
La MaMa Experimental Theatre Club in the
East Village.
Balm in Gilead premiered at La MaMa in 1965, directed by
Marshall W. Mason. The play was revived in 1984 by
Circle Repertory Company and the
Steppenwolf Theatre Company, and directed by
John Malkovich. Later in 1965, Wilson wrote and directed
Miss Williams for a
benefit performance at La MaMa called "BbAaNnGg!". In 1965, Wilson's plays
Home Free! and
No Trespassing were produced for La MaMa Repertory Troupe's first European tour. His play
This is the Rill Speaking was produced alongside
Jean-Claude van Itallie's
War and
Rochelle Owens'
Homo for La MaMa Repertory Troupe's second European tour, in 1966. His play
Untitled was produced with work by
Sam Shepard,
Tom Eyen,
Leonard Melfi,
Paul Foster, and Owens, all directed by
Tom O'Horgan, for La MaMa Repertory Troupe's third European tour, in 1967. In addition to writing his own plays at La MaMa, Wilson did set design for work by other playwrights. In 1966, he designed the set for Foster's
The Madonna in the Orchard, directed by O'Horgan at La MaMa. He then designed the set for Donald Julian's
In Praise of Folly, directed by Mason at La MaMa in 1969. Wilson's play
The Sand Castle was first produced at La MaMa in 1965, as directed by Mason, and was again directed by Mason at La MaMa in 1967. Wilson participated in the inaugural National Playwrights Conference in 1965 at the
Eugene O'Neill Theater Center along with
Sam Shepard,
Edward Albee, and
John Guare. His 1966 play
The Rimers of Eldritch addressed hypocrisy and narrow-mindedness in a small town in the rural Midwest and won the 1966/1967
Drama Desk Vernon Rice Award for contribution to off-Broadway theatre. It was first produced at La MaMa in 1966, under Wilson's direction. Wilson directed a revival of
The Rimers of Eldritch at La MaMa in 1981 in celebration of the theater's 20-year anniversary.
The Rimers of Eldritch was followed by
The Gingham Dog (1968) about the breakup of an interracial couple. He returned to the O'Neill Theater Center to develop
Lemon Sky in 1968. Wilson described
Lemon Sky (1968) as "directly autobiographical". The play's narrator Alan, Wilson's representation of himself, describes his attempt to reconcile with his long-absent father. They fail to meet each other's expectations, and Alan leaves disillusioned by his father's authoritarianism and narrow-mindedness. ==Circle Repertory Company and later work (1969–2011) ==