NewEnglandFilm.com

The drifter philosopher must be an archetype as old as art itself, but someone’s always coming up with a refreshing version, similar enough to be recognized yet unique enough to hold your interest. The latest entry of the bunch is the wandering hobo Winston (Michael Henderson) in S.G. Collins’ "The Same Side of Rejection Street." Winston is a poet-preacher-philosopher who, when he first appears onscreen, contemplates the evils of our society as he clambers out of a dumpster. It’s not long before Winston meets Catherine (Karen Ball), a perpetual loser who is incapable of making it through a job interview without both unwittingly and then intentionally insulting her potential employer. The two hit it off in unexpected ways. Thus the story begins.

The film takes place throughout the course of a single day, as Winston and Catherine push and pull against each other, both of them irritated yet intrigued by the other’s presence, as they wander through the Boston streets. What first seems like an unlikely connection starts to make more sense as the film unfolds.

Winston, a master manipulator, is capable of coaxing just about anything he wants out of people, whether it’s a new hat or a $50 bill. People do what he tells them to do. Catherine, on the other hand, constantly feels pushed around. She asserts herself at inappropriate times only to buckle when she should stand firm. She’s the malleable sort, always being used by people sharp enough to realize they can push her around. She does what people tell her to do — everything, that is, except go away. She doesn’t like rejection, and she has a certain whining persistence that, in its own way, can be endearing. So the two can’t seem to get rid of each other, as if it were fated that they meet.

Rambling muses like Winston always seem to have wounds that haven’t quite healed, a dark secret or two in their past, and Winston is no exception. Hidden tragedies are the downfall of many a film when they fail to live up to expectations. Happily, in this film, the tension doesn’t depend on the revelation at all. We watch because we want to find out how Catherine and Winston interact. We want to know what will happen to these two people who have stumbled upon each other, seemingly headed toward some sort of meaningful connection. The past here is incidental; it’s their future we care about. "The Same Side of Rejection Street" is an amusing and engrossing film due largely to the flesh-and-blood portrayal of the characters.

Perhaps they are more than mere types after all.