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.