How I Became a Ramblin’ Man is the second in a trilogy of short costume dramas Rodney Graham produced between 1997 and 2000. The film is a musical-Western genre piece in which the artist, dressed as a benign wandering cowboy, rides his horse through a prairie landscape, eventually stopping to sing a melancholic song about his solitary country life. He then rides away, with each shot mirroring the sequence of his arrival. Like much of Graham’s practice, the film explores the structure of the loop and the playing of a role. The film’s circuitous structure denies the possibility of narrative resolution, suggesting instead an endlessly repeated journey.