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Shepard moved to New York City in 1963 and found work as a busboy at the Village Gate nightclub. The following year, the Village Gate's head waiter, Ralph Cook, founded the experimental stage company Theater Genesis, housed at St. Mark's Church in-the-Bowery in Manhattan. Two of Shepard's earliest one-act plays, "The Rock Garden" and "Cowboys", debuted at Theater Genesis in October 1964. It was around this time that Steve Rogers adopted the professional name Sam Shepard.
In 1965, Shepard's one-act plays Dog and The Rocking Chair were produced at La MaMa Experimental Theatre Club. These were the first of many productions of Shepard's work at La MaMa during the 1960s, 1970s, and 1980s. In 1967, Tom O'Horgan directed Shepard's Melodrama Play alongside Leonard Melfi's Times Square and Rochelle Owens' Futz at La MaMa. In 1969, Jeff Bleckner directed Shepard's play The Unseen Hand at La MaMa. The Unseen Hand later influenced Richard O'Brien's musical The Rocky Horror Show. Bleckner then directed The Unseen Hand alongside Forensic and the Navigators at the nearby Astor Place Theater in 1970.
Shepard's play Shaved Splits was directed at La MaMa in 1970 by Bill Hart. Seth Allen directed Melodrama Play at La MaMa the following year. In 1981, Tony Barsha directed The Unseen Hand at La MaMa. The production then transferred to the Provincetown Playhouse and ran for over 100 performances. Syracuse Stage co-produced The Tooth of Crime at La MaMa in 1983. Also in 1983, the Overtone Theatre and New Writers at the Westside co-produced Shepard's plays Superstitions and The Sad Lament of Pecos Bill on the Eve of Killing His Wife at La MaMa. John Densmore performed in his own play Skins and Shepard and Joseph Chaikin's play Tongues, directed as a double bill by Tony Abatemarco, at La MaMa in 1984. Nicholas Swyrydenko directed a production of Geography of a Horse Dreamer at La MaMa in 1985.
Several of Shepard's early plays, including Red Cross (1966) and La Turista (1967), were directed by Jacques Levy. A patron of the Chelsea Hotel scene, he also contributed to Kenneth Tynan's Oh! Calcutta! (1969) and drummed sporadically from 1967 through 1971 with the band The Holy Modal Rounders, appearing on their albums Indian War Whoop (1967) and The Moray Eels Eat The Holy Modal Rounders (1968). After winning six Obie Awards between 1966 and 1968, Shepard emerged as a screenwriter with Robert Frank's Me and My Brother (1968) and Michelangelo Antonioni's Zabriskie Point (1970).
Cowboy Mouth, a collaboration with his then-lover Patti Smith, was staged at The American Place Theatre in April 1971, providing early exposure for Smith, who became a well-known musician. The story and characters in Cowboy Mouth were inspired by Shepard and Smith's relationship. After opening night, he abandoned the production and fled to New England without a word to anyone involved.
Shortly thereafter, Shepard relocated with his wife and son to London. While in London, he immersed himself in the study of G.I. Gurdjieff's Fourth Way, a recurring preoccupation for much of his life. Returning to the United States in 1975, he moved to the 20-acre Flying Y Ranch in Mill Valley, California, where he raised a young colt named Drum and rode double with his young son on an appaloosa named Cody. Shepard continued to write plays and served for a semester as Regents' Professor of Drama at the University of California, Davis.
Shepard accompanied Bob Dylan on the Rolling Thunder Revue of 1975 as the screenwriter for Renaldo and Clara that emerged from the tour. However, because much of the film was improvised, Shepard's work was seldom used. Rolling Thunder Logbook, his diary of the tour, was published in 1978. A decade later, Dylan and Shepard co-wrote the 11-minute song "Brownsville Girl", included on Dylan's 1986 album Knocked Out Loaded and on later compilations.
In 1975, Shepard was named playwright-in-residence at the Magic Theatre in San Francisco, where he created many of his notable works, including his Family Trilogy. One of the plays in the trilogy, Buried Child (1978), won the Pulitzer Prize, and was nominated for five Tony Awards. This marked a major turning point in his career, heralding some of his best-known work, including True West (1980), Fool for Love (1983), and A Lie of the Mind (1985). A comic tale of reunion, in which a young man drops in on his grandfather's Illinois farmstead only to be greeted with indifference by his relations, Buried Child saw Shepard stake a claim to the psychological terrain of classic American theater. True West and Fool for Love were nominated for the Pulitzer Prize. Some critics have expanded the trilogy to a quintet, including Fool for Love and A Lie of the Mind. Shepard won a record-setting 10 Obie Awards for writing and directing between 1966 and 1984.
In 2010, A Lie of the Mind was revived in New York at the same time as Shepard's new play Ages of the Moon opened there. Reflecting on the two plays, Shepard said that the older play felt "awkward", adding, "All of the characters are in a fractured place, broken into pieces, and the pieces don't really fit together," while the newer play "is like a Porsche. It's sleek, it does exactly what you want it to do, and it can speed up but also shows off great brakes." The revival and the new play also coincided with the publication of Shepard's collection Day out of Days: Stories. The book includes "short stories, poems and narrative sketches... that developed from dozens of leather-bound notebooks [Shepard] carried with him over the years."
Shepard began his film acting career when cast in a major role as the land baron in Terrence Malick's Days of Heaven (1978), opposite Richard Gere and Brooke Adams. This led to other important film roles, including that of Cal, Ellen Burstyn's character's love interest in Resurrection (1980), and, most notably, Shepard's portrayal of Chuck Yeager in The Right Stuff (1983). The latter performance earned Shepard an Academy Award nomination for Best Supporting Actor. By 1986, Fool for Love was adapted by Robert Altman with Shepard in the lead role; A Lie of the Mind was being performed Off-Broadway (with Harvey Keitel and Geraldine Page); and Shepard was working steadily as a film actor. Together, these achievements put him on the cover of Newsweek.
Over the years, Shepard taught extensively on playwriting and other aspects of theater. He gave classes and seminars at various theater workshops, festivals, and universities. Shepard was elected to the American Academy of Arts and Letters in 1986, and was elected a Fellow of the American Academy of Arts and Sciences in 1986. In 2000, Shepard demonstrated his gratitude to the Magic Theatre by staging The Late Henry Moss as a benefit for the theatre, in San Francisco. The cast included Nick Nolte, Sean Penn, Woody Harrelson, and Cheech Marin. The limited, three-month run was sold out. In 2001, Shepard played General William F. Garrison in the film Black Hawk Down. Although he was cast in a supporting role, Shepard enjoyed renewed interest in his talent for screen acting.
Shepard performed Spalding Gray's final monologue Life Interrupted for the audiobook version, released in 2006. In 2007, Shepard contributed banjo to Patti Smith's cover of Nirvana's song "Smells Like Teen Spirit" on her album Twelve. Although many artists had an influence on Shepard's work, one of the more significant was Joseph Chaikin, a veteran of The Living Theatre and founder of The Open Theater. The two worked together on various projects, and Shepard has stated that Chaikin was a valuable mentor.
In 2011, Shepard starred in the film Blackthorn. His final film appearance is Never Here, which premiered in June 2017 but had been filmed in 2014. Shepard also appeared in the television series Bloodline from 2014 to 2017.
At the beginning of his career, Shepard did not direct his own plays. His early plays had a number of different directors, but were most frequently directed by Ralph Cook, the founder of Theatre Genesis. Later, while living at the Flying Y Ranch, Shepard formed a successful playwright-director relationship with Robert Woodruff, who directed the premiere of Buried Child (1982). During the 1970s, Shepard decided that his vision for his plays required him to direct them himself. He directed many of his own plays from that point onward. With only a few exceptions, he did not direct plays by other playwrights. He also directed two films but reportedly did not see film directing as a major interest.