Given that he's worked with some of the best directors on the planet both on the screen and stage, Philip Seymour Hoffman would seem a natural to step behind the camera. But with the quirky and moribund Jack Goes Boating Hoffman flails wildly, telling a story about unlikeable people living in grim New York apartments who are only interesting due to the bizarre and implausible things they to do improve their lives. It's an adaptation of a play by Bob Glaudini that wears its theatrical roots poorly, taking little advantage of New York scenery or the power of the camera to tell this slight story.
Starring four well-paid actors who pretend somewhat poorly to be average working-class folks, Jack Goes Boating is one of those stories in which no one has what they want, and they're too paralyzingly insecure to do anything about it. Hoffman is heftier and more pitiful than ever as Jack, a limo driver whose only friends are fellow driver Clyde (John Ortiz) and Clyde's wife Lucy (Daphne Rubin-Vega). Clyde and Lucy decide they've had enough of Jack and his patheticness so they set him up with Connie (Amy Ryan), who works with Lucy at a Brooklyn funeral parlor and is the slimmer, prettier female equivalent of mousy and mumbling Jack.
Yes, Jack and Connie are so sad that you are forced to root for them, particularly after Connie is attacked on the subway and Jack starts taking swimming lessons so he can take Connie on that titular boat ride once summer arrives. And the fiery relationship between Clyde and Lucy, fraught with innumerable rifts after years of marriage, reveals some heartbreaking truths about love and longevity, even if it eventually explodes into sub-Who's Afraid of Virginia Woolf? histrionics. But between the inarticulate characters, the awkward plot devices-- swimming and cooking lessons for Jack, numerous sexual attacks for Connie-- and the bleak New York winter, you feel trapped with these people who have allowed their lives to become mundane hells and for some reason are forcing you to share it with them.
The acting is the main reason to slog through, and though Hoffman is never as good in schlubby everyman mode as when he's allowed to play with a little darkness, the rest of the ensemble usually balances him out. Ryan is basically doing The Office's Holly Flax without the endearing goofiness, but she convincingly creates Connie a woman burned out enough to consider a dreadlocked Philip Seymour Hoffman sexy, and to treat a home-cooked meal as the ultimate romantic gesture. Rubin-Vega and Ortiz show a lot more range as Clyde and Lucy repeatedly squabble and make up, and as a couple they're generally likable, but they spend so much time propping up the morose Jack that their life gets sucked out as well.
It's possible to defend Jack Goes Boating as one of those rare movies that's for and about adults, that addresses real stakes in real relationships and, for God's sake, gives actresses as good as Rubin-Vega and Ryan some meaty screen roles. But good intentions don't make a worthwhile story, and despite a few flourishes behind the camera, experience in good films doesn't make Hoffman a worthwhile director-- at least not yet. Give him material a little less stagebound and contrived and I'm still willing to believe he'll have something to bring to the table next time.