[2] In 1976 Woodruff established the Bay Area Playwrights Festival, a summer forum for the development of new plays that is still flourishing.
The thirty-three-year-old playwright was still better known in London than the States, and his collaborations with Woodruff marked a turning point in both men's careers.
For the next five years Woodruff was virtually the sole director of Shepard's work, staging the American premiere of Curse of the Starving Class at the New York Shakespeare Festival in 1978, the world premieres of Buried Child (1978) and True West (1980) at the Magic Theatre in San Francisco and then in New York, and the touring productions of Tongues and Savage/Love, which Shepard co-authored with the performer Joseph Chaikin.
In 2002, Woodruff succeeded Robert Brustein as the artistic director of the American Repertory Theater in Cambridge, Massachusetts.
Woordruff left in 2007 when his contract was not renewed because of concerns that Woodruff's artistic approach would affect the theater's profitability.