As with most of Philip Seymour Hoffman’s work, Jack Goes Boating is a heavily character-driven story, one that invests its audience in the intricacies and quandaries of the lives of two working-class couples in New York City. Each character is brilliantly realized by an exceptional cast, fully immersing the viewer in the ups and downs of each relationship and the anticipations, expectations, and insecurities of finding love. Though visually and rhythmically the film resembles a play (it’s based on the 2007 stage play by Bob Glaudini), its strengths lie in its emotionally charged characters, especially Jack, whose struggles in life are both bizarre and humorous, yet still charming and believable.
Jack (Philip Seymour Hoffman) is an aging limousine driver in New York City with a taste for Reggae and ambitions of landing a job with the MTA. With little experience in love, Jack is coerced into a blind date with Connie (Amy Ryan) by his married friends Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega). Both eccentric and timid souls, Jack and Connie make a connection and he begins taking cooking and swimming lessons to impress her. When Jack prepares a dinner party for Connie at Clyde and Lucy’s home, his attempts at constructing the perfect evening are steadily unraveled by the despair lurking beneath his friends’ seemingly happy relationship.
Jack goes boating is a very small film, not only in the sense of budget and the limited number of characters and sets, but also in the scope of its ideas. This will, unfortunately, lead to little box office success. However, it will inevitably please fans of stage plays and those who appreciate average characters that deal with the minutiae of everyday life. The roles are mildly interesting, quirky, awkward, and played by an experienced cast of actors, but nothing particularly stands out about Jack and his friends. He’s the most sympathetic of the bunch, but not enough to be more than a meager amusement. They deal with trifling situations, are introverted, have few goals and fewer accomplishments, are survivors but not overachievers and are odd by general standards. Pointless is too strong a word, but Jack Goes Boating is definitely a film that will only appeal to those who already know what it will be like before watching it.
The music is very prominent, issuing a new song at the start of just about every scene, tying together montages and enlivening moments that might not otherwise have importance. The significance of each action is usually left to the viewer to decipher, with the camera marooned on faces and expressions, carefully studying their idiosyncrasies; their thoughts are occasionally easy to guess, with contentment or sadness being the predominant moods. The delivery of dialogue is also painstakingly surveyed, surrounding regular activities such as eating dinner, driving, working, or swimming. Like real life, some things go smoothly; others turn out disastrously, with these events approached in a calm, understated method. At least there is subtle humor throughout, even in darker moments, from a subway altercation to infidelity to a ruined feast. It’s entertaining but not profound, and perhaps too artsy for most.
– The Massie Twins (GoneWithTheTwins.com)