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).
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).