Review of Win Win (2011) by Chris S — 05 Sep 2011

I had heard so much about Win Win all year long. I skipped screenings for it early on in the year mostly because I'd never heard of it, but also because on the surface it's not exactly something I'd want to actively hunt down and see. But it gained such a reputation for being a fantastic film and is even considered to be a contender for film of the year by several fellow movie critics. So thanks to word of mouth, this found its way into my Blu-ray player. Win Win manages to make good on its reputation.

Mike Flaherty (Paul Giamatti) is one of the best lawyers in town. Unfortunately, being the best doesn't always mean you make the most money. Mike is facing a lot of financial hardship at the moment and it looks like his elder law firm may go out of business. Mike talks his way into becoming the guardian for Leo Poplar (Burt Young), one of his clients on the verge of dementia which he plants in a retirement home in order to get an extra $1500 a month. So things are looking up until Leo's grandson Kyle (Alex Shaffer) shows up to live with his grandfather. Kyle is a troubled teenager, but an incredible wrestler. So of course Mike has Kyle move in with him. With the extra money and Kyle on the verge of going to state, everything seems to be falling into place for Mike. That is until Kyle's Mom, Cindy (Melanie Lynskey) comes to town and ruins the bright future that was right within Kyle's grasp.

Paul Giamatti has always been fairly compelling in whatever film he's decided to be a part of. Even if the project isn't very good, Giamatti is usually still memorable thanks to his performance. He's outstanding in Win Win. He seems to be making all the decisions he thinks are right to keep his family afloat. It's incredibly easy to picture yourself in Mike's shoes and making the same decisions that he did. Alex Shaffer is also great, but for different reasons. Kyle is mostly a young man who doesn't speak much. His appearance makes him come off as if he's a punk, but he's actually a fairly goodhearted individual with a really messy past. That past gets in the way of the one thing that could possibly push Kyle forward in life and he carries that weight throughout the movie. It's only a matter of time before he snaps. Bobby Cannavale and Amy Ryan deserve a mention, as well. Terry Delfino has a lot going on in his life right now and being an assistant coach is basically a distraction from what his ex-wife is currently putting him through. His laid back attitude and ability to be a bit more outspoken than he should is half the character's charm. Meanwhile, Jackie Flaherty just wants to do what's best for her family and begins to care for Kyle. She has some pretty funny dialogue throughout the film, especially her JBJ story.

One of Win Win's strongest attributes is the fact that the dialogue feels very natural. Nothing feels forced or sounds cheesy. It all sounds like things real people would say if they were thrown into the life of the Flahertys. The film also delivers an incredible message, which is something other films like this that have been released this year have either lacked or haven't fully followed through on. Win Win wears its heart on its sleeve and capitalizes on that in the best of ways.

Win Win is a special kind of movie. The excellent cast compliments the already superb writing in the film while characters and their decisions are easily relatable. It packs a powerful punch, especially in its last act as the message it gives is both strong and meaningful. Win Win is easily one of the strongest (if not THE strongest) R-rated comedies of the year with little to no flaws to keep note of.