The structure Burns employs here will remind certain viewers of a comparable storytelling strategy on TV's Once and Again. Conventional scenes of dialogue and action are intercut with the characters talking into the camera about their lives as if they are being interviewed. Unlike the TV show, however, an unseen and apparently omniscient interviewer sometimes even poses questions. The majority of these interviews are conducted on the bustling sidewalks of Manhattan, hence the film's title.
The subjects of such queries as "How and when did you lose your virginity?" include Maria (Rosario Dawson), a twentysomething sixth grade teacher; Tommy (Burns), a 32-year-old celebrity-interview television show producer; Ben (David Krumholtz), a twentysomething hotel doorman and rock band wannabe; Ashley (Brittany Murphy), a 19-year-old college student and diner waitress; Griffin (Stanley Tucci), a 39-year-old dentist; and Annie (Heather Graham), a 31-year-old real estate agent.
Their lives intertwine this way: Griffin is married to Annie, but he's a devout adulterer, and he's currently spending his lunch hours in sexual congress with Ashley, whom he picked up in Central Park with a barf bag of bull about how she looks like a model. Ashley is so gone over Griffin that she's always whining about wanting to be something more to him than a lunch-hour quickie. That attitude endures until Ashley meets Ben, who attracts her with a barf bag of bull about how she's the most beautiful woman he's ever seen. Yes, Ashley would seem to have personal-appearance issues.
Ben used to be married to Maria, but he cheated on her until she dumped him. Maria is so burned out on men she hasn't had sex since her marriage broke up. That changes, however, when she meets Tommy in a video store and ends up in the sack with him before the tape can rewind. A friend assures Maria that she hasn't really had sex, of course, because she and Tommy limited their amour to oral-genital contact. Out of an apartment and staying with a friend because he just broke up with his girlfriend, Tommy is really leery about starting another relationship too soon. But he really digs Maria. Which is too bad because after a second date when they do "go all the way," Maria dumps him because she's leery of starting another relationship too soon. Meanwhile, Tommy becomes attracted to Annie, the real estate agent trying to help him find a new apartment. But she's married, and he's not going there. Now, of course, when Annie discovers that Griffin is sleeping with Ashley, even though he isn't any longer, she wants a divorce and Tommy's phone number. Which is fine except that we're petrified Maria might get a toothache.
All of this is perfectly diverting and frequently quite funny. Burns writes good dialogue straight out of the Woody Allen script primer. Ben has all the stock Allen neuroses without the attendant Allen brains. Annie's last name isn't Hall but maybe her maiden name was. In a line lifted almost whole cloth from Allen, Griffin is a man who comes home sweaty from his health club because he doesn't like to shower with other men. Griffin is also terribly insecure about the size his of sexual equipment, setting up exchanges with first Ashley and then Annie that are among the film's funniest.
Undeniably pleasant and well acted as this is, however, particularly by Dawson and Murphy, Sidewalks of New York nonetheless lacks much artistry. The interview strategy is distracting and inconsistent. Burns' reliance on jerky jump cuts probably saved him a lot of money on re-shoots, but I'm among the viewers who've always been irked by this technique. The premise that one doesn't have to have movie-star good looks to attract gorgeous women is borne out in the remarkable romantic conquests of Ben and Griffin. What doesn't make quite as much sense is that both Ben and Griffin are such jerks. The latter is a sexual predator with almost no redeeming qualities, but at least he makes good money. The former is so dumb he thinks Iowa is somewhere around Atlanta. His work as a doorman isn't a day job to support his musical ambitions; it's a career path. His only apparent romantic attributes are unquenchable lust and an infinite supply of flattery. Now, if I had only known Ben's formula back when I met Michelle Pfeiffer, I might have mentioned that she is beautiful.