Jack Goes Boating marks the directorial debut of one of America's most accomplished and one of my personal favorite actors, the brilliant Philip Seymour Hoffman. The man has been a spark in such films as Spike Lee's touching 25th Hour and the Charlie Kaufman-helmed surrealist mind-bender Synecdoche, Ny. His direction here is understated, his film shambling but not entirely bleak. Jack Goes Boating is a drifting picture, but it is a winner because of its heart. It could have, given the subject matter, a relentlessly dour experience. Instead, Hoffman incorporates both the happy and the sad in mostly equal measures. A small film, but a success.
The film centers on a neurotic, rasti-loving New York limo driver with a penchant for pot and a nearly overwhelming sense of day-to-day isolation. He latches onto a couple whose marital fabric is stretching from past indiscretions, through whom he is introduced to an equally neurotic young woman named Connie who seems to have a good if oft-trampled heart.
In some ways, Jack Goes Boating feels a lot like a Cheever or a Raymond Carver short story. There is not a lot of action, the story centering mainly on character interactions. It is plodding but never dull. There are many surprises, actually, such as a weird subway scene and a dinner party climax for the ages. Despite what its detractors will no doubt claim, the film strikes a resonant tone. It seems "real", for lack of a better word. Hoffman's performance is understated but always reliable and Amy Ryan is excellent as the damaged Connie. The two leads are ultimately a conjoined foil for the other couple whose marital pains provide the film's moral center, as well as dramatic tension.
Indie enthusiasts take note, the soundtrack is also quite interesting. Though the song choices are generic, the bands represented are some of my favorites, Grizzly Bear and Fleet Foxes among them. Ultimately, this is a soft film with a lot of memorable scenes, snappy dialogue and while it may meander, that is its charm. Very poignant.