Filmed in October 2008 on the eve of Obama's historic election and an unprecedented economic crisis, this lyrical portrait of New York City follows WFMU radio reporter Clay Pigeon as he takes to the streets to talk to fellow New Yorkers about their lives, their dreams, and their relationship with a transforming city. As part of what he calls a “radio experiment,” this transplanted Iowan roams the streets bearing a handheld recorder and a kindly probing nature: “Has he popped the question?” “When is the last time you’ve had a regular roof over your head?” “Do you love America?” These revealing interviews are woven between vivid scenes of New York’s eccentric byways, which together reveal a city—and a nation—at a crossroads.