"Made with Pride in the U.S.A." is how the filmmakers describe the production process in the end credits of Sidewalks of New York. The movie is made with energy and a resourceful shooting style that encourages a sense of speed and unobtrusive movement — the camera follows the characters in action, rather than viewing them at a distance.
We are the audience with Tommy (Edward Burns), the outer-borough guy uncomfortable with his own success, as he pursues Maria (Rosario Dawson) a young teacher who has been out of the dating game since her divorce. We endure slick seducer Carpo's (Dennis Farina) advice on how to "score." Then we witness Maria as Benjamin (David Krumholtz), her boyish ex-husband, tries to win her back but fails with spectacular style. We switch to follow Benjamin, as he avoids surprisingly sensible advice from his band mate Gio (Michael Leydon Campbell) and locks his heart and hopes on a pretty waitress. Ashley in turn, is tied up in an affair with a married man Griffin (Stanley Tucci), whose neglected trophy wife Annie (Heather Graham) meets Tommy and starts to consider what might happen next...
Burns' story structure is based on following these lines of connection. Emotional intersections seem almost random at first, but then separate each story flows together as characters come into conflict and resolution. For all its "run-and-gun" energy, Sidewalks of New York reveals itself to be a carefully interwoven "circle of love," much like Max Ophuls' graceful classic La Ronde (1950). Another film of the early 1950s was also a strong influence for Burns: the Italian neo-realist anthology picture Amore in Citta (1953), in which a young Federico Fellini and Michelangelo Antonioni (along with four other directors) explored episodes of romance in Rome.
"I wanted to capture the way it feels to be alive in New York City right now,' Bums says, "To show people in the midst of their lives, making choices, making changes. I wanted to have the feeling of an investigation — to tell the story of a wide range of characters, but still get close to each one of them. Shooting a tight-knit story in an immediate style, drawing the audience into the process — it seemed to me the way to go."
"Working with Spielberg on Saving Private Ryan, I saw how quickly and effectively Spielberg could work by using a handheld camera and available light. Being an independent filmmaker who works with lower budgets, I thought, 'why not use those tactics to make my film more quickly and cost efficient, while also creating a sense of immediacy and intimacy in the storytelling?" says Burns.
He continues: "Being an independent, not having anyone looking over our shoulder, is a freer way to work." Once Burns and his crew decided they could shoot without conventional coverage, they lost the need to dress every set for the reverse. The same apartment could be broken up and employed for four different uses: Annie and Griffin's living room, an elevator interior, Hilary and Harry's yuppie dining room and Maria's doctors office. Actors shared one wardrobe trailer which also served as rehearsal space to prepare for upcoming scenes. The film was shot throughout the streets of New York in 17 days.