(2011, written and directed by: Thomas McCarthy, starring: Paul Giamatti and Amy Ryan)
Great characters looking for something in life and "Win Win" just might be that something.
As in Thomas McCarthy's first film, "The Station Agent", there is an air of loneliness to the characters in "Win Win" but also with an ability to be kind and with a whole lot of humour permeating throughout. Mike (Paul Giamatti) is approaching a mid-life crisis; the monotony of daily life and money troubles colliding. But this is a well written film and it doesn't look or feel like a mid-life crisis.
Just as we get to know the characters exceedingly well (despite the short air time for some - Bobby Cannavale's Terry), a plot is introduced. Mike starts acting like a sleazy lawyer just to make some easy money, even though he's anything but a sleazy lawyer. Because he's a good guy, realities quickly catch up, and he starts taking responsibility for a troubled kid. Mostly trying to assuage his guilt of wrong-doing, but this kid happens to be a wrestling phenom and Mike is a struggling high school wrestling coach. This film could easily turn into an underdog sports story, but as I said before, this is a well written film and it doesn't look or feel like an underdog sports story.
I found "Win Win" to be a great mix of character study, a mid-life crisis, and an underdog sports story all rolled into something that isn't any of the above. It's a light, funny, enjoyable slice of life that could provide a few lessons on morality but stops itself before it becomes condescending.