Win WIn (2011)

This film is hard to categorize--it is part drama, part sports movie, part comedy, and not easily pigeon-holed, but it is wonderfully entertaining without being formulaic.
The center of the movie is Paul Giamatti as Mike Flaherty, an attorney whose life is unraveling because his business failing. When his daughter Abby (Clare Foley) is told by mom Jackie, the family's moral center (Amy Ryan), that her dad is out running, her immediate reply — "From who?" — and this is more on the mark than any of them know.
As if Mike's business problems weren't bad enough, he also volunteers as a coach for the remarkably unsuccessful high school wrestling team.
So what does he do? He does something sleazy. He petitions for guardianship of a client under the false pretense that he will do a better job than the state, but turns around and immediately turns around and does exactly what they would do, and pays himself to do so. How does this end up well?
Out of nowhere, Kyle, the client's grandson, shows up and he is one enigmatic, phlegmatic young man. His mother is in drug rehab, and her boyfriend has beaten him up, so he takes a chance on the grandfather he doesn't even know. All he has is that his mother hates him, so maybe he is actually a good guy. He has one ace up his sleeve (besides his genuine affection for the grandfather). Wouldn't you know it, the kid is one terrific wrestler. (McCarthy, who co-wrote the story with Joe Tiboni, took a chance and cast a real-life high school wrestler who'd never acted before, and Shaffer shows what a wise choice that was.)
Kyle moves in with Mike's family, they actually come to adore him, and he makes a real difference to the team by not only wrestling but coaching his teammates and playing the part of a leader who seemingly doesn't have any ego in the mix.
Watching all these permutations work themselves out is so enjoyable it is easy to forget that "Win Win" has adroitly hooked us into a story whose impressive moral trajectory deals with issues of fallibility, culpability and more. The director (who did the wonderful film 'The Visitor') puts over these big issues with a graceful feel for tiny moments, for a wealth of sly and subtle looks between actors. He manages to be respectful of and sympathetic to all his characters' diverse viewpoints while having a strong position of his own. It is a win-win situation indeed.