Sidewalks of New York is a 2001 romantic comedy-drama film directed by Edward Burns. The film focuses on six New Yorkers whose lives intersect as they search for love and companionship in the city that never sleeps. The characters include Tommy (Edward Burns), a television producer who has just been dumped by his girlfriend, Maria (Rosario Dawson), a young woman who works as a real estate agent and is searching for a wealthy man to marry, Annie (Heather Graham), a kindergarten teacher who is unhappy in her marriage, Benjamin (David Krumholtz), a young man who works in a coffee shop and is trying to find true love, Carpo (Dennis Farina), a middle-aged man who owns a bar and is having an affair with a much younger woman, and Ashley (Brittany Murphy), a college student who becomes romantically involved with a much older man.
The film is presented in a non-linear format, with each character's story being told separately in a series of interviews and flashbacks. The film explores the complexities of modern relationships and the challenges of finding lasting love in a city as big and chaotic as New York. It received mixed reviews from critics, but was praised for its sharp dialogue, strong performances from the ensemble cast, and its realistic portrayal of contemporary urban life.