Glaudini's script is amazingly nuanced and is given life by performances that match it in subtlety. Hoffman's Jack is particularly great, especially in his character's explication of the film's theme of the importance of our illusions: those that destroy us, those that motivate us, and those that merely keep us going. For Jack, these stories are vital; we get the impression that the only way he has been able to make it through his lonely existence is by investing himself blindly in an optimism that is illusory and ironic. Lonely and depressed, he has no concrete reason to harbor such optimism, but he clings to it nonetheless. In addition to Hoffman's stellar performance, the film's co-stars offer something very special, particularly Ortiz. Clyde, like Jack, is similarly controlled by mental images. However, while Jack's illusions are optimistic, Clyde's mind is filled with visualizations of his wife's infidelities, and just as Jack suffers a brief mental breakdown at a dinner party, Clyde's fixation on the image of his wife with another man threatens their relationship that night.
Though the direction is somewhat stagey, resulting in a few tonally awkward moments, "Jack Goes Boating" features solid writing and fully realized performances that allow it to transcend such missteps and tell a tale that is worth the optimism surrounding Hoffman's ascent to the director's chair.
Genre: Black Comedy. Written by: Bob Glaudini. Directed by: Philip Seymour Hoffman. Starring: Philip Seymour Hoffman, Amy Ryan, John Ortiz, Daphne Rubin-Vega.