Warmly observed and solicitous of its audience to the point of caress, Win Win is as comfortable an experience at the movies as you might have this year. Writer and director Tom McCarthy (The Station Agent, The Visitor) specializes in light humanism (or humanism lite), storytelling that features recognizable people facing their recognizable lives with just a little more grace and good nature than is recognizable. The flourish there at the end lends McCarthy's understated, involving approach a bit of self-affirming flattery: These people look and sound just like me, therefore, I am as endearing and ultimately decent as these people.
If only it were true. Win Win's origin fib is that its characters are "ordinary" people and not well-stitched ideals (even the "bad" ones are filet cuts of badness), but McCarthy is so deft a student of human speech and so tender an observer of human interactivity that it's easy to ignore the seams. Paul Giamatti is back in genial, long-suffering mode as Mike Flaherty, an elder-care attorney with a failing practice, two young children, and a skeptical wife, Jackie (Amy Ryan). Mike's latest client, Leo (Burt Young), doesn't want to leave his home but is, perhaps, no longer capable of taking care of himself. "Perhaps" is good enough for an impatient, clogged up legal system to sentence a forgetful man to the old folks' home, especially if his only relative, errant daughter Cindy (Melanie Lynskey), is unreachable.
Mike is in a more calculable decline: "I don't know, work, money -- everything" is the problem, he tells his friend Terry (Bobby Cannavale), a big city lawyer to Mike's country counsel. When it comes out that Leo's estate could support a $1,500/month fee for an at-home guardian, Mike decides to offer himself for the job, then put Leo in a home and pocket the money anyway. The amount -- not that much, not nothing -- seems key to mitigating Mike's deception; it's a choice that sets his desperation into relief even more starkly than it suggests his transgression. The entitlement that often accompanies the legal profession (or attracts people to it in the first place) does not come naturally to Mike, a lack that some -- like Terry, who does very well, despite having just lost his house in a divorce -- see as a glitch. Winners succeed, they prosper, they find loopholes and then they close them when no one is looking.
The arrival of Leo's grandson, Kyle (Alex Shaffer), puts a kink in Mike's winning plan. Kyle is a runaway who's sick of his mom's drug problems, and his unreconstructed coolness is at first mistaken by the Flahertys for the usual teen angst bullshit. As it happens, Kyle's just in control, especially on the wrestling mat, where he blows away the team Mike coaches in his spare time. Shaffer is a wonderfully calm, quizzical presence on screen, and much of the ribbing humor of the film's midsection derives from the awe with which the grown men (including Jeffrey Tambor as Mike's assistant coach) treat their bleach-topped ringer. It's broad, sports movie stuff, but it works on the strength of performances perfectly suited to McCarthy's ability to use both language and silence to reveal character and modulate the film's comic rhythms, which are impeccable. Giamatti and Ryan are reaction-shot geniuses, and it's a pleasure to watch them stretch out in the breathing room McCarthy builds into his scripts.
Kyle is assimilated into the Flaherty family almost immediately, first out of necessity and then because it turns out he's a nice kid in a tough spot in addition to being an all-around baller. Thus the film builds up to both the big, scholarship-securing wrestling tournament and the big reveal of Mike's deception -- which he keeps up without much note -- when Kyle's mom finally hits the scene looking for a payout. Again, the alternative McCarthy proposes for Leo and Kyle suggests that while Mike may not be doing the right thing, he's not wrong. It's too easy and is resolved too conveniently, yet you'll leave Win Win smiling, half-sedated with the illusion that things just might turn out for you, too.