By Nate Freiberg

Philip Seymour Hoffman is an actor who makes good film choices. Excepting 2006’s Mission: Impossible III – a probable cash grab in which he had some fun as villain Owen Davian – Hoffman has anchored a steady string of strong films since capturing his Best Actor Oscar for 2005’s Capote. And given the spotty post-Oscar careers of Halle Berry, Adrien Brody and Forest Whitaker, this is by all means worth mentioning. His movies might not always be as high-profile as Charlie Wilson’s War, but from The Savages to Before the Devil Knows You’re Dead to Doubt, Hoffman can be counted on to put his considerable talents to good use.

That trend has continued with the modest Jack Goes Boating, in which Hoffman not only plays the title character but takes his first spin as a director as well. Adapted by Robert Glaudini from his play of the same name, Jack Goes Boating rides the superlative performances of Hoffman and co-star Amy Ryan to deliver an amusing – but above all – honest and fresh look at two shy people coming together in the early stages of a relationship.

Jack (Hoffman) is a working-class New York City limo driver thinking about applying for a job at the city’s Metropolitan Transportation Authority. Timid and introverted, he can usually be found underneath his large headphones and woolen winter cap, listening to a cassette tape of reggae music with his blonde dreadlocks occasionally coming into view.

A decent guy, Jack begins to emerge from his shell after meeting Connie (Ryan) on a blind date set up by his best friend and fellow limo driver, Clyde (John Ortiz). Timid in her own way as someone we get the sense was hurt years ago and hasn’t gotten involved since, Connie and her genuine and frank nature prove disarming for Jack, who is almost immediately taken by her and undergoes a regimen of self-improvement to win her over. With Clyde’s help, Jack takes both swimming and cooking lessons, leaving his firmly established comfort zone along the way.

As a work originally performed on the stage, Jack Goes Boating’s biggest strength is, perhaps unsurprisingly, its characters. Here are real people who experience real problems and whose relationships develop in natural, organic ways. Jack and Connie don’t “meet cute,” and their first few evenings together are full of the sort of awkwardness and nervous, guarded emotion we might expect from two people like this. And while the problems and story arc that Clyde and his wife, Lucy (Daphne Rubin-Vega), endure are hardly new, there’s not a moment in which they’re not believable as three-dimensional people, the kind which we might come across on a daily basis.

Though not an outright comedy, the film is also funny. The humor is of a subtle variety, though that didn’t stop the audience from frequently erupting in laughter during the screening I attended. That’s a credit mostly to Hoffman — whose facial expressive work is as good as ever – and the other actors, whose timing with the dialogue is first-rate. Hoffman, Ortiz and Rubin-Vega are all reprising their roles – having starred in the play Off Broadway – and that experience together clearly goes a long way here. Ryan fits in seamlessly, contributing to a great ensemble production.

Where the film lags is when it focuses too heavily on the weary, troubled marriage of Clyde and Lucy. Their plot thread effectively serves as an established counterpoint to the new, exciting beginnings of Jack and Connie, but we enjoy watching Hoffman and Ryan onscreen together so much that when Ortiz and Rubin-Vega are given greater footing during a climactic dinner party in the film’s final act, we yearn to get back to the other couple. That’s no fault of the actors – though Ortiz and Rubin-Vega aren’t on the same level as Hoffman and Ryan, they’re both more than capable. It really boils down to Glaudini’s script, which in this case, doesn’t quite survive the shift in formats.

As a director, Hoffman shows real promise. By finding interesting places for the camera, he confidently avoids the static, monotonous feel we often get when smaller-scale plays are adapted for the big screen. Technically, he excels as well, patiently allowing scenes to breathe and inventively blending in Jack’s preparatory mental visualizations of swimming and cooking before he actually does so. The scenes of Clyde’s teaching Jack how to swim are a real standout, simultaneously entertaining and touching.

Unfortunately, it may be awhile until we see a follow-up effort from Hoffman. In a post-screening panel discussion and audience Q&A hosted at New York’s 92Y, Hoffman made no effort to hide the difficulties he encountered behind the camera, particularly when the “differing personalities” of Hoffman the director and Hoffman the actor failed to get along. Fortunately, any divisive energies he may have experienced while making the film aren’t apparent in the final product, though Hoffman could certainly be excused for not wanting to undergo the process again.

Jack Goes Boating may be small in scope, but in true indie fashion, that merely allows the actors to take center stage. Fans of Hoffman and Ryan in particular would do well to seek this one out.