Jack (Philip Seymour Hoffman) is a limousine driver in New York City who has never had a steady girlfriend, in spite of being in his early forties. This is something his best friend Clyde (John Ortiz) is painfully aware of, and he seeks to remedy that situation by introducing him to someone his wife Lucy (Daphne Rubin-Vega) works with at a funeral director's. She is Connie (Amy Ryan), who is also a shrinking violet and in truth not all that good at her job either, meaning she might be sacked soon if she doesn't improve fast. Clyde introduces Jack and Connie over the kitchen table in his apartment, and though they are both shy and reluctant, there's a definite connection there...
That is until Connie gets to talking about her recently deceased parents and has to retreat to the bathroom to compose herself, but even then it could be that love finds a way. Jack Goes Boating was the sole directorial effort by star character actor Philip Seymour Hoffman, and his obsessively hardworking nature was displayed in the way this married both his passions, film and the theatre. It was adapted by Robert Glaudini from his own play which Hoffman and co-stars Ortiz and Rubin-Vega had appeared in together: Amy Ryan, fast becoming one of the most respected character actresses around, was the new addition to the cast, and she worked very well with her director.
In fact, so good were the central couple that they almost forgave the more unlikely contrivances of the plot. Hoffman was all too able at portraying losers and sad sacks, and though it was a mark of his talent that he displayed remarkable range in his sadly curtailed career he seemed drawn to finding the humanity in characters who had been cast aside by life, the sort of people few were making movies about in such three-dimensional personality-building as he could achieve. So you may well observe Jack was not much of a stretch for him, and he was playing it safe in his first movie where he was also at the helm, but then again why not test the waters with something you knew you were perfectly good at?
After all, he may have branched out into something more challenging to direct later on, we'll just never find out. And besides, Hoffman's acting of such a cowed character was something he could have played in his sleep, but he never offered that impression, as his commitment was there for all to see: when movie stars turn to making their own pictures, they can either give themselves a plum role or generously submit centre stage to other performers. What was interesting about this was Hoffman was doing both, papering over the cracks in a script which would have been easier to take in the theatre by encouraging his cast, as well as himself, to construct personas where you may have misgivings about the way things unfolded - the singlalong was more absurd than believable - but you had faith in the actors.
Really we were intended to contrast the tentative but pure love of Jack and Connie as they creep by increments towards a relationship, with the title referring to the date they are planning half a year in the future, and the marriage of Clyde and Lucy hitting the rocks. They spend so much time ensuring their two friends get together as if in denial that their own partnership has seen much of the romance wave goodbye some time ago, and really Clyde may be composed on the surface, but he's even more messed up than Jack appears to be, as after all Jack is just a sweet guy who never had the chances in life which would allow him to blossom. Predictably, this is what happens by the point the end credits begin to roll, but such contentment is hard won when you have the disastrous dinner party to get through: seriously, if you must indulge in drug abuse at least eat the meal first. Some saw this as a comedy, but it's a shade too painful to really laugh at, and that's a credit to the four leads who under Hoffman's sensitive direction were allowed to shine. Music by Grizzly Bear.