The Dogwalker (1999)

Jerry Cooper is The Dogwalker, a Tom Sawyer grown up for the nineties, who having fallen on hard times, is struggling with the reality of having to sleep in his car. When he quite literally stumbles upon an old lady and her dog, he suddenly finds himself caught up in her life and over her head in a twisted mix of class, race, age, sex, drugs, dog leashes, inheritances and contract bridge.