Philip Seymour Hoffman has long since solidified himself as one of the very best character actors working today, moving from role to role and genre to genre and fitting in just about every time. Whether he's playing an adult film camera operator (Boogie Nights) or famous author Truman Capote (Capote), to name but a couple, Hoffman is consistently brilliant and always enjoyable to watch.
Adding another awkward yet likeable character to his resume in the awkward yet still somehow sweet Jack Goes Boating, Hoffman proves his acting talent once more (he also impresses as first-time director). Admittedly this film version isn't exactly a stretch for him considering he has played the very same character many times in the Broadway play by Robert Glaudini. But still there's something that feels freshly cinematic about the adaptation (a thing many film versions of plays don't seem to accomplish), and Hoffman is essentially playing a character who acts/reacts in the realistic way most of us would in these kinds of social situations.
The film tells the story of the eponymous Jack who leads a perfectly normal but ultimately unfulfilling life as a limo driver. One day he meets Connie (played by the always wonderful Amy Ryan) and after a date or two they both make arrangements to go boating during the summer. The trouble is Jack doesn't know how to swim and so gets his best friend to help him (who's having relationship troubles of his own) while continuing to try and impress Connie.
Jack Goes Boating is one of those modern American comedies in the vein of Sideways and The Kids Are All Right which doesn't really have much of a plot but relies heavily on character interactions and "everyday" dialogue. That type of film can produce varying degrees of success but Jack Goes Boating luckily is one of the better ones.
It's not exactly Curb Your Enthusiasm level of situational discomfort (but really what is?), however it does keenly capture that feeling of public awkwardness that we've all felt at one time or another. For instance, on their first date Connie reveals that her father was in a coma but woke up suddenly supposedly (according to Connie) to help her mother who is in a nursing home. However, not long after waking up he fell in a hallway and hit his head and died. Hoffman's uncomfortable reaction to this info is completely believable and relatable - just what the hell are you supposed to say in that kind of a situation? That's just one example of the awkwardness which Jack Goes Boating achieves with aplomb.
Reminiscent of the work of directors such as Alexander Payne and Tom McCarthy (who coincidentally makes an appearance as Connie's boss here), Jack Goes Boating is perhaps not the best example of this type of thing but it's a solid effort. Hoffman continues to prove his worth as one of the best actors in the business and shows definite skill as a director with this well observed character study.