Last month, I rewatched Sidewalks of New York, a 2001 romantic comedy directed by Edward Burns. I’m almost watching this in a historical context, because it is representative of the kind of late 1990s indie romantic comedies that are just full of talking and neurotic characters. It’s definitely a thing from Woody Allen movies, which carried over into the indie film boom of the 90s, and is around today in the form of indie movies about millennial hip gentrifiers obsessed with their romantic lives.
The film also takes a bit of the mockumentary style, with talking head interview clips with the characters, and it’s never established who the “documentary filmmakers” are, they just show them at random on NYC street corners talking about sex and love and relationships. The film quality is also slightly grainy and always has a bit of a shaky handheld feel to it. It comes off like HBO’s Real Sex when they would have interview segments asking random couples on the street about sex, or the first season of Sex & the City, which resembled more of a 90’s indie film with rough edges before it got more fashionable and polished.
It feels dated in part of the constant walk and talk, how characters date by just asking out random strangers they meet by chance in video stores or cafes, and how the Twin Towers are framed prominently next to Edward Burns’ head in his character’s interview scene.
It has a good cast (Burns, Heather Graham, Brittany Murphy, Stanley Tucci, Rosario Dawson, David Krumholtz) with interconnected stories tying current and former couples with each other, and a lot of talk about infidelity and messy romantic histories and the like. They flow well with each other and make the connections feel believable, like they would cross paths with each other in Manhattan.
Watching this also reminds me of seeing this around age 18 in my hometown art house movie theatre, being an inexperienced kid watching a movie about neurotic NYC adults and their confusing romantic lives. Luckily, this kind of interconnected drama has never figured in my life.
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