Jack Goes Boating (2011)

Directed by Philip Seymour Hoffman
Written by Robert Glaudini

Boat rides throughout history have been somewhat of a mixed bag in terms of outcome. When I think of boat rides, not being seasick, is the relaxing, placid waters that come with a nice boat ride with nice people. However, there is a horrendous nature too and one of the first tragedy’s that comes to mind is the Titanic, which left thousands freezing in the cold waters of the North Atlantic. Another, more fictional, example would be Gilligan’s island, which is somewhat similar to what this film does. They took a three hour tour, but tragically were blown off course and shipwrecked. But that television show was a comedy where characters were funny and good things happened on that island. The captain leisurely reclined in a hammock. So while boat rides can be choppy, they can also be soothing.

Jack (Philip Seymour Hoffman) is a down on his luck limo driver who works for his uncle in New York City. But when I say down on his luck, I mean it socially, as he has few friends, and even fewer prospects for friends, and more importantly for girlfriends. But his few friends, couple Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega) help him immensely, setting him up with one of Lucy’s co-workers, Connie (Amy Ryan), who is an equally down on her luck, middle aged woman. Jack really likes Connie, and starts to take steps to turn his luck around, but at the same time, the relationship between Clyde and Lucy becomes strained.

Jack Goes Boating marks the directorial debut of one of the most interesting, and accomplished, actors of the last decade or so, Philip Seymour Hoffman and while this film will not go down perhaps as all that accomplished, I will say that Hoffman makes an interesting debut effort. And part of what works in this film is the cast, while includes none other than Philip Seymour Hoffman in the main role. But those around him are quite good too, most notably the Academy Award nominated Amy Ryan. Ryan and Hoffman work really well together in roles I would not have expected to see them in, especially Ryan whose work I’ve seen usually revolved around her being a strong minded individual. But here she and Hoffman play the broken, socially awkward yet extremely likable and endearing characters Connie and Jack. They really work nicely together.

The other two, John Ortiz and Daphne Rubin-Vega, also give solid performances, but their tale is much more of a roller coaster ride than Jack and Connie’s. Their marital strife surfaces just when their friend Jack is starting to fall in love, creating and strange dynamic. The emotional roller coaster ride of the plotlines is sadly mirrored by its handling by director Hoffman. Sometimes it works, and other times the notes are missed and it rings false. However, there is a certain strength in honesty, which is when this film is at its best, when it is being honesty, and Jack and Connie’s relationship feels honest.

The film definitely has an indie feel to it however. The soundtrack is at times poignant while at other intruding and obvious. It is sometimes too cutesy and the scenes including the casual consumption of pot and hookah seem unnecessary and forced given the story trying to be told. But the ambition and brightness created by the relationship between Jack and Connie, on both sides, is beautiful to behold, and Hoffman and Ryan are great with their oddball chemistry that somehow works. For a debut work it shows promise to the future of Hoffman in the director’s chair and at the same time shows why he is still one of the best actors working today.

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