While he was rehearsing his play The Late Henry Moss in San Francisco in the fall of 2000, Sam Shepard invited film director Michael Almereyda (Hamlet, Nadia) to document this process. The playwright states: "Every play is a discovery. You create a framework, and leave something open in the hope you will discover something . . . Every time you write, you're approaching a certain kind of secret. And as you approach it, the audience is approaching it too."

In this drama, two brothers played by Nick Nolte and Sean Penn struggle to come to terms with the death of their raging alcoholic father ((James Gammon). Others in the play include Woody Harrelson, Cheech Marin, and Sheila Tousey. There are sidebar interviews with music composer T Bone Burnett and lighting designer Anne Militello.

Although the material being covered Shepard's play is serious (family strife, the frustration of men, the quest for father), the filmmaker conveys the playful creativity that is at the core of the rehearsal process. In one of the most entertaining sections of the documentary, Sean Penn talks about being compelled to a career in acting after seeing the zipper boots of an actor who visited his high school. Shepard claims he was attracted to acting by "that thing that Burt Lancaster did with his teeth." Shepard comes across as the Renaissance man that he is with glimpses and reminiscences of his career as a playwright, film director, actor, screenplay writer, and published author of short stories, poems, and autobiographical diversions.

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