The Dogwalker (2002)

Jerry Cooper is a dogwalker, a Tom Sawyer grown up for the nineties, who, having fallen on hard times, is struggling with the reality of being forced to sleep in his car for the first time. When he, quite literally, stumbles upon an old woman and her dog, he believes his luck may finally be changing as the woman’s family hires him to take care of the flinty old matriarch, Alma, and her less than well-trained pooch, Lucky. But he quickly finds out that he’s gotten a bit more than he bargained for, between babysitting Alma, her dog, and a trio of elderly bridge-playing suitors, while at the same time juggling the attentions of Alma’s smug, self-centered daughter, Helen, and Helen’s preternaturally sexual teenage daughter Susan. So when Jerry enlists the aid of three black friends to help with the unique demands of his newly adopted family, the two disparate factions are soon headed onto a collision course of class, race, sex, drugs, dog leashes, inheritances and contract bridge that not even a skilled conniver like Jerry can avert.