Jack Goes Boating (trailer above) arrived in our mailbox the other day. Philip Seymour Hoffman both directs (his debut) and stars as Jack, a severely timid and unsophisticated man who works as a limo driver for his uncle’s company in Manhattan. Halting and monosylablic, Jack’s primary hope in life seems to come from listening to “Rivers Of Babylon,” by the Melodians, on his cassette Walkman.

But Jack does have a friend — a good one — in his co-worker Clyde (the keen John Ortiz). Clyde and wife Lucy (Daphne Rubin-Vega) decide to set Jack up with Lucy’s new co-worker at Dr. Bob’s Funeral Home — Connie, who has been hired to do phone solicitations for Dr. Bob’s grief seminars.

Played by Amy Ryan, whom we enjoyed as Steve Carell’s dorky love interest Holly Flax on The Office, Connie is the last person you’d imagine as a phone solicitor. She is emotionally fragile to the point of withdrawing to the bathroom for crying jags when we first meet her having dinner with Clyde, Jack, and eventually Lucy.

Connie’s parents have both died, but that alone does not explain her debilitated psyche, which is one of the difficulties with this story. No explanation is given of how both Connie and Jack became so inhibited.

Regardless, they’re clearly perfect for each other, and the dinner at Clyde and Lucy’s leads to Connie accepting a future outing with Jack. He wants to take her boating — which is odd because it’s snowing when he asks, months away from any boating weather. Also, Jack has no swimming experience whatsoever.

Thus unfolds the sweetness of Jack’s friendship with Clyde, who will help him learn to swim and generally take steps forward in the world, as well as in his relationship with Connie. Unfortunately, this personal growth coincides with some cracks in Clyde’s own relationship with Lucy, and none of these difficulties are improved by recreational drug use.

As Jack, Philip Seymour Hoffman is a bit of a blank. We know that he likes Connie and we see his concentration as he visualizes and hones his swimming and cooking skills, but we never know him well enough to really care for him. As a director, Hoffman gives us a slow but professional film which includes a couple of interminable scenes, and also several strong moments of humans close to the breaking point.

There’s more to cheer for in Amy Ryan, whose glimmer of heroism is less clouded by marijuana smoke. We may not know the source of Connie’s personal pain, but we can at least discern its shape and see who she is when she steps out from behind it.

Both unknown to us before this, the intensity between John Ortiz and Daphne Rubin-Vega is perhaps the best surprise in this film. She is subtly cunning and driven, and he is everything from elegant to tender to pitiful at various points — sometimes one after the other. Their mutual maneuvering is fairly electric, and in one scene his restlessness is simply perfect.

Before making this film version, Hoffman, Ortiz and Rubin-Vega performed together in the off-Broadway production of Jack Goes Boating, a play by Bob Glaudini. The movie does have a play’s close personal encounters — but does not suffer from the rote recitation or stock sets of many adaptations from the stage. It actually feels more like documentary than theater.

Jack Goes Boating is a worthwhile 91 minutes that will have you thinking about its characters (and humming “Rivers Of Babylon“) for days afterward. I rate it 3 out of 4 stars.

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