Mike Flaherty (Paul Giamatti) has been feeling stressed of late. He's a New Jersey lawyer whose caseload is not exactly enormous, his offices could do with getting a new boiler because his partner in the firm Stephen Vignam (Jeffrey Tambor) has had the thing examined and apparently it could explode at any minute, the tree outside his house is in danger of falling down, and a myraid other things need seeing to which cost something Mike does not have: a surplus of money. However, after yet another panic attack there is a ray of hope...
But it might also spell his downfall, for he takes on a new responsibility which could earn him enough cash to get through his troubles. This is becoming the guardian of one of his clients, Leo (Burt Young), and elderly man who wishes to stay in his home but is being pressured to move to residential care. The best thing Mike could do would be to take Leo in as he promised and look after him, but he's concerned, as many of the characters here are, with taking the easiest route possible, so Leo does indeed go into that old folks' home and Mike begins to use the money he earns for the old geezer's upkeep to keep his own head above the financial water.
If this is beginning to sound like some dry, miserable drama then in writer and director Tom McCarthy's movie there would be surprises in store, one of them being how funny it could be. There were a good number of laughs here, not from blatant quips and gags, but from humour arising from the interplay of character which his cast proved most adept at conveying. Giamatti was predictably ideal as the harrassed modern male putting a brave face on things even as he staves off a life of desperation, but he brought out the best in his co-stars as well, with Amy Ryan no-nonsense as Mike's wife Jackie, and Bobby Cannavale very amusing as his divorcé friend who has a knack for saying the wrong thing.
With every character down to the smallest role painted with care and attention to bring out the best in the film, this was an entertainment for those who liked to see actors in an environment conducive to their finest work, even if it looked effortless on the screen. The next complication in Mike's world - because that's the way he lives, from complication to complication - is that Leo has a grandson, Kyle (Alex Shaffer), who really should be with his mother (Melanie Lynskey), or he should have been if she wasn't an unreliable recovering drug addict. While Leo goes to the home, Kyle moves in with Mike, mainly because he has seen how terrific at wrestling the boy is.
That matters due to Mike being the coach for the failing wrestling team at the local high school, and they seriously need a win, but as time goes on he comes to sympathise with the kid and feel like a father to him. Shaffer's refusal to play the role as your typical teenage rebel makes for an interesting tension (he was cast for his grappling abilities), and as the family get to like having him around there grows to be more at stake than simply the money - what happens when Kyle finds out this isn't happening entirely out of the goodness of Mike's heart? It's true McCarthy doesn't quite avoid turning this to soap opera by the end, but the engaging acting makes the results very likeable, and genuinely unusual in its premise, not because it's a strange plot or anything, but due to the way it ventures to places your average drama wouldn't think of, or at least to arrange them in this fashion. With fine work all round, Win Win may be basic indie movie fare when you boil it down, but it is very enjoyable, even poignant by its close. Music by Lyle Workman.