I know it's odd but the first thing that struck me about Win Win was that the film was rated R for language. Having seen it, the rating seems unfair and a bit misleading. Thomas McCarthy's (The Station Agent, The Visitor) film is a gentle examination of relationships being forged by real people who happen to talk the way real people talk. There is no artifice to be found and this organic approach is McCarthy's greatest strength and the film's most endearing virtue.
Mike Flaherty (Paul Giamatti) is a decent man who is about to enter morally questionable territory. By day he works as an elder care lawyer and at night he coaches the local high school's wrestling team. Unfortunately his practice isn't doing too well as he feels the pinch of supporting his wife, Jackie (Amy Ryan) and their two daughters. When he comes across a wealthy client, Leo Poplar (Burt Young), who would like to live on his own but lacks legal guardianship, Mike oversteps his bounds. He becomes Leo's guardian under the pretense of setting him up in his own house but pulls a bait and switch when no one is looking. Next thing you know, Leo is staying in an elder care facility and Mike is pocketing the monthly stipend for being Leo's guardian.
Before Mike can get used to the idea of an easy paycheck, a quiet kid named Kyle (Alex Shaffer) shows up on Leo's doorstep claiming to be his estranged grandson. With Leo in no position to take care of the boy, Mike and Jackie take him into their own house until he can go back home to his mom, Cindy (Melanie Lynskey), who is in rehab at the moment. While Jackie is initially apprehensive about a strange teenager staying with them, Mike quickly delights in the fact that Kyle is an ace wrestler who may just be able to reverse the fate of his high school wrestling team. Just as Kyle starts to come out of his shell and life settles into a pleasant rhythm, Cindy comes around looking for daddy's cash and asking questions that could get Mike in trouble. Any way you look at it, somebody is about to be pinned to the mat (sorry).
Make no mistake about it. On paper, Mike Flaherty seems like an opportunistic jerk. First he lies about the details of an old man's living arrangement for a monthly pay raise. Then he takes interest in a boy who may have run away from a neglectful (and potentially abusive) home just because he can improve the prospects of a shitty wrestling team. There is nothing about the character that should scream compassion and yet that is exactly what Giamatti's performance and McCarthy's deft hand have created. Giamatti plays Mike with a quiet desperation that reminds us he isn't evil. He made a mistake in a moment of weakness and hasn't found the best way to make amends yet. How he chooses to treat Kyle is the fork in his road to redemption, even though he doesn't recognize that at first.
Speaking of Kyle, it would be an understatement to say that Alex Shaffer is the surprise star of the film. In his film debut, he perfectly captures the brusque low-key persona that everyone associates with disenchanted teens. If that described the entirety of Kyle's character then Shaffer would have an easy task ahead of him. However, McCarthy presents Kyle as an enigmatic individual who draws you in even as you try to figure him out. Shaffer is more than up to the challenge and dominated my attention whenever he was on screen. While Giamatti and Shaffer make up the film's emotional core, the rest of the capable cast surrounds them in excellence. Amy Ryan puts on a tough front but is easily the sweetest character in the film. Jeffrey Tambor and Bobby Cannavale are also on hand as Mike's friends and comic relief.
McCarthy, who also wrote the screenplay, imbues the film with a subtle humor that doesn't demand laughs but frequently earns smiles. He treats his characters with kindness because this is not the sort of film that requires us to wallow in misery. Even Cindy, who could be considered the villain of this piece, shows the potential for largesse if you squint at her final scene just right. McCarthy focuses on the innocence that people possess when they aren't busy getting in their own way. Not everybody gets what they want but they all get what they deserve...thus, the clever title.
Video & Audio:
In Conversation with Tom McCarthy and Paul Giamatti at Sundance 2011 give us a brief interview with the director and star of the film as they go into character descriptions and examine the central moral dilemma for Mike. Family takes this concept further as the entire central cast weighs in on their characters in the film through a series of quick interviews. This is followed by a Music Video for Think You Can Wait by The National which plays over the end credits. The song is a lovely bit of melancholy and the video features footage from the making of the film. We close things out with a Theatrical Trailer for the feature and Sneak Peeks for other films.