James and Hugo share the elation and struggle of their creative aspirations amidst the harsh realities of economic survival in a megalopolis. The film follows the pair, with their paints and easels, onto the streets. It is a place where one’s joy and ache can be likened to a flower's pushing its way up through a crack in the sidewalk.
Filmmaker Michael Jacobsohn takes an intimate look into the lives of two unmistakably talented people:
James is homeless by choice. He prefers the expanse of the wide-open sky, sleeping under Central Park’s trees—except on rainy nights when he takes refuge on city pavement under city scaffolds. His outdoor way of life is fundamental to his plein-air canvases.
On the other hand, Hugo would much prefer to have a permanent roof over his head. He has walked away from a successful small business to devote himself entirely to his artistry. Now impoverished financially, he yearns for a warm, safe place to live and practice his crafts: paint his canvases and play his music, usually 14 hours a day.
Jacobsohn lives conventionally on New York’s Upper West Side, married and financially secure. In retirement, he devotes endless hours in pursuit of producing and directing feature-length documentaries.
The dissimilar lifestyles of the three in no way define them: It is their common commitment to creativity that fulfills, resonates, and endures.