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Win Win tells the story of Mike Flaherty (Paul Giamatti), a down-on-his-luck lawyer who becomes the legal guardian of one of his aging clients. However, he gets more than he expected when the client’s estranged grandson Kyle (newcomer Alex Shaffer) shows up in town as a runaway.
The idea of Paul Giamatti starring in an indie dramedy as a schlubby middle class guy is not exactly groundbreaking, but that hardly matters, because Win Win is so good. No, it may not offer anything new to the genre, but it’s a quietly funny, heartfelt tale that barely ever hits a false note.
Everyone in the cast is good. Giamatti, as always, brings the perfect combination of neuroticism and charm, while Amy Ryan shines as his tough-talking wife with a big old soft heart. To me the real standout was Bobby Canavale as Mike’s divorced, aimless high school buddy, Terry. Canavale is hilarious, and he brings energy to a film that could otherwise feel a bit too low-key. Terry’s charismatic, but he’s also a douchebag, and Canavale deftly brings out both sides in equal measure.
The story is simple and slow, but that definitely works in the film’s favour. Every character seems fully fleshed out, and as a viewer, you feel totally immersed in Mike’s world. My only complaint is with a character who doesn’t show up until part way through the film (I don’t know if revealing that character would qualify as a spoiler, but I like to err on the side of caution). Their presence seems to interrupt the flow of the story a bit, and while that’s the point, I feel like that character is painted a tad too one-dimensionally in order to move the plot along.
That said, though, Win Win, is an expertly constructed, well-acted film. When done well, I really enjoy character studies, and this is a great one. It’s kind of like Greenberg without some of the hints of pseudo-intellectual quirk, and Up in the Air without some of the glossy finesse.