Stan Herd (John Hawkes) is a talented earthwork artist who creates masterpieces out of environmental elements such as rocks, plants, wood, and vegetation. After spending a lot of his personal money on these projects in Kansas, this still unknown crop artist has reached a crossroads in his creative work. Photographer Peter Kaplan (Bruce MacVittie), one of his most enthusiastic fans, encourages him to assemble one of his artworks in New York City. In 1994, he suggests he use property owned by Donald Trump before a new tower is constructed on the land. Herd secretly takes out a second mortgage on his home without telling his wife (Laura Kirk) and then makes a bid to do his new project for free on the multi-acre lot on the Upper West Side.

The Midwestern artist rents a hotel room but soon finds himself sleeping on the site to protect it from being used as a dump for garbage and large castaway objects and appliances. What comes as a complete surprise to Herd is that his project only becomes a reality thanks to the help of a band of homeless men who volunteer to help him. They include an African-American poet (Sam Greenlee), a graffiti artist (Chris Bachand), a handy man and a schizophrenic (Zach Grenier)who at first is nothing but trouble but then turns out to be another ally.

Earthwork is based on the true story of crop artist Stan Herd and the challenges he faced in sharing his rural artwork with a larger urban audience. Writer and director Chris Ordal pinpoints the central message in this drama: "To make a living via your passion, one must manage everything that the modern world has thrust upon us, then explore that passion long enough for someone to notice." In other words, it takes not only passion but patience and perseverance to make a living based on one's creativity. Perhaps the sweetest surprise of all in Herd's nine-month adventure in the Big Apple is the camaraderie of the homeless men who collaborate with him on his urban earthwork.

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