Philip Seymour Hoffman’s directorial debut, Jack Goes Boating, isn’t going to go down as one of the great debut works and it’s not going to set the world—or even the box office—on fire. It is, however, a genial, shambling little film with characters it’s possible to care about even when you don’t necessarily like them. Every so often—usually by the way he has intercut scenes—Hoffman evidences some significant flair as a filmmaker, but in the main, this is very much an actors’ film. That’s hardly surprising since it was made by an actor—and it’s not to the detriment of the film.
A bigger stumbling block is the fact the film is adapted from a play. Don’t jump to the conclusion that that translates into something stagey. Jack Goes Boating only feels stagey in its “big scene,” and that feels stagey more because it has the theatrical feel of contrivance than because of a lack of cinematic style. The scene simply feels like a scene. Overall, the film is intelligently opened up without seeming to fret about being cinematic.
Jack Goes Boating is largely a four-character affair. Other characters are necessary to the plot, but they never take the focus off the main four. Jack (Hoffman) is a man with no social skills of any kind and a fairly simple dream of moving from being a limo driver for his uncle’s company to being a driver for the New York City MTA. His best—seemingly only—friend is fellow limo driver Clyde (John Ortiz, Public Enemies), who tends to serve as a kind of mentor, despite the fact that both men are about the same age (early 40s). Clyde has a wife, Lucy (stage actress Daphne Rubin-Vega), who works for a funeral home with her friend, Connie (Amy Ryan, Changeling). Since Connie is fully as socially and sexually awkward as Jack, it follows that Clyde and Lucy think the two should hook up.
It turns out that this isn’t a bad idea in its own right, but it has its own set of problems. Jack and Connie are drawn to each other, but can only view the possibility of some kind of relationship in terms of something down the road. “Down the road,” in this case, means making a tentative date to go boating in the summer (a date arranged in the dead of winter) and a vague plan that Jack will cook dinner for Connie. In another sense, this isn’t all bad because Jack doesn’t know how to swim or cook. Clyde can teach him the former, but since neither Clyde nor Lucy know anything about cooking, outside help is required in the kitchen.
All this, of course, sets the stage for the dinner party, which is the film’s aforementioned big scene. Since so much rides on this event, it follows in terms of drama that everything that can go wrong will go wrong. What sets this apart from so many movies and plays that have used this basic device is that it isn’t played for comedy, but as a kind of mini-tragedy through which underlying qualities and flaws—some irreparable—in the characters are revealed. You watch what unfolds with the kind of grim fascination usually reserved for an accident scene—hoping that the worst won’t happen, but knowing that it will. It’s almost powerful enough to overcome the sense that it’s a scene—but only almost. In this case, however, “almost” is good enough, thanks to the filmmaker’s obvious sympathy for his benighted characters. Rated R for language, drug use and some sexual content.