It’s not giving anything away to say that Jack Goes Boating, the directorial debut of Philip Seymour Hoffman, began life as a play that enjoyed a successful run Off-Broadway in 2007. But it’s worth keeping this in mind, because the film’s strengths and weaknesses are strongly bound up with its theatrical origins.

The first great strength of Jack Goes Boating is its willingness to closely examine the relationships among a quartet of non-glamorous New Yorkers well past the bloom of youth. The second is that it features outstanding performances by the four principals (three of whom were also in the off-Broadway production): Philip Seymour Hoffman, John Ortiz, Daphne Rubin-Vega and Amy Ryan (taking the role played by Beth Cole in the play). These are excellent actors willing to dig deep and reveal their characters’ inner workings. Hoffman elicits strong performances from all four, as well as from a number of supporting actors in minor roles added for the film.

Preserving original-cast productions of successful plays is an fine old tradition in the film business and one that allows those of us who don’t live in New York a chance to experience the next best thing to being in the theatre. Seriously, you’d have to be a stern purist to argue that Tod Browning should not have captured Bela Lugosi’s performance of Dracula on film, and, despite Edward Albee’s objections, we’d be poorer could we not enjoy the performances of Elizabeth Taylor, Richard Burton, George Segal and Sandy Dennis in Mike Nichols’ film version of Who’s Afraid of Virginia Woolf? And let’s not forget the sublimely guilty pleasure of Mervyn LeRoy’s film version of Bad Seed, which preserved some of the most delightfully scenery-chewing performances in the history of film.

So I’m glad to have a version of Jack Goes Boating on film, even if it is not wholly successful in that medium. The problem is that the film still feels like a play, except that now actors are saying their lines on the snowy streets of New York or at an improbably uncrowded municipal swimming pool. Jack Goes Boating does capture the feeling of being in New York (a task at which many big-budget films such as Date Night fail miserably) but never convinces us that its characters live real lives there. Instead, all too often they seem like characters in a minor, if sincere, play who wandered into a foreign universe. Their artfully-crafted dialogue and occasionally mannered deliveries (Mamet-speak can work marvelously well on stage but seldom on film: a notable exception being James Foley’s film of Mamet’s own Glengarry Glen Ross) clash with the feeling of reality that the film otherwise seems bent on establishing.

But enough about that. What’s good about Jack Goes Boating makes it worth seeing, particularly if you’re a Philip Seymour Hoffman fan. He plays Jack, a schlub who drives for a limo service (not as glamorous as it sounds—they’re basically an alternative version of a taxi cab), wears a silly stocking cap indoors and out, and appears never to have been intimate with anyone in his entire life. Then one day his co-worker Clyde (John Ortiz) sets him up on a blind date with the fetching but insecure Connie (Amy Ryan), who does telephone sales for an oily funeral home proprietor and motivational speaker (Thomas McCarthy). You’ve seen indie relationship films before, so you can guess where this one is going. What sets it apart is the amount of detail the actors bring to their performances. Another bonus is the fact that Hoffman is as interested in the shifting relationships among three pairs of characters—Jack and Connie, Clyde and his wife Lucy (Daphne Rubin-Vega) and Jack and Clyde—as he is in the changes in the individual characters. If you noticed that Connie and Lucy have no relationship to speak of, I can only say welcome to the American theatre, which can be just as much a boy’s club as Hollywood.

Jack Goes Boating is a film of many excellent moments that offer fair compensation for the fact that the whole doesn’t really work. Like the dialogue, the action lurches from the intimate to the exaggerated (what in the world is up with that attack on the subway and who’s paying the hospital bills?). But if you can summon a sufficiently generous spirit to overlook it occasional ham-fistedness, you will be rewarded with some fine acting that delivers a sense of what made this story work on stage. | Sarah Boslaugh