Sidewalks of New York (2001 film)

The circle begins with Tommy Reilly, a onetime wannabe writer who became the producer of a weekly television entertainment news show by design rather than choice, and has stayed with it for the money rather than any professional satisfaction. Dumped by his live-in girlfriend without warning, he temporarily moves in with colleague Carpo, an aging Lothario ready to offer unlimited — and sometimes useless — romantic advice.

At a video store, Tommy meets grammar school teacher Maria Tedesko. The two flirt, meet for coffee and begin to date. Maria, recently divorced, finds it difficult to commit to a new relationship and stops taking Tommy's calls. When she discovers she's pregnant, she attempts to reconnect with him, but at the last moment opts to lie and tell him she's leaving town and chooses to raise the child on her own.

Maria's ex-husband, who longs to reconcile with her, is Benjamin Bazler, an apartment house doorman and aspiring songwriter whose obsession is 1960s/1970s rock music. He shares his dream of becoming a full-time musician with Iowa transplant Ashley, an NYU student working as a coffee shop waitress to support herself.

Ashley is involved in an affair with considerably older married dentist Griffin Ritso. Although he professes to love his mistress, the once divorced Griffin shies away from leaving his wife Annie Matthews for fear of being a two-time loser at matrimony. Eventually, Griffin's inability to commit to their relationship causes Ashley to dump him and reject his advances to get her back as she becomes involved in a relationship with Benjamin.

Real estate broker Annie is unhappy with her marriage but too moral to consider having an affair. She finds herself confiding in and flirting with one of her house-hunting clients — Tommy Reilly. Thus the circle is complete. She finally leaves Griffin.

The narrative segments are intermingled with documentary-like interviews in which of the characters address the camera with their thoughts about sex, love, and relationships.

• Edward Burns as Tommy Reilly
• Rosario Dawson as Maria Tedesko
• David Krumholtz as Benjamin Bazler
• Brittany Murphy as Ashley
• Stanley Tucci as Griffin Ritso
• Heather Graham as Annie Matthews
• Dennis Farina as Carpo

Burns wrote the script while on the set of Saving Private Ryan.^[4] Filming began on February 23, 2000 and wrapped on March 16.^[5]

In an episode of the Sundance Channel series Anatomy of a Scene that focused on the film, Burns revealed he shot the film in only seventeen days, working with a budget of $1 million.^[4][6] Many of the locations used were within the same neighborhood in order to facilitate a quick move from one to the other.^[4] Dennis Farina's scenes were shot in one day; he had agreed to the low budget production after meeting Burns on the set of Saving Private Ryan.^[7] Tucci and Graham both shot their scenes in under a week.^[6]

The film premiered at the Toronto International Film Festival on September 8, 2001. Following the terrorist attacks three days later, Paramount Classics, who had reportedly spent $2 million on the domestic distribution rights,^[5] withheld its release until late November.^[8][9] Although the World Trade Center looms behind Tommy during his interviews, the image of the twin towers in the original promotional poster was later deleted.^[10]

The film played on 224 screens and grossed $2,402,459 in the United States. The international box office accounted for another $1.1 million.^[3]