"Worth a watch but don't expect it to be anything memorable."

Rating: 7/10 (3 March 2011)

Win Win is a moderately heartwarming and quiet comedy (I'm not going to call it a dramedy - I hate that word) that is oddly difficult to synthesize into a few sentences; I will crudely try my best. Mike (Paul Giamatti) is a poor man's lawyer and high school wrestling coach who struggles with money issues. One day he makes an immoral decision and becomes the guardian of a wealthy elderly man primarily to collect the $1,500 monthly check he is rewarded. The next day the grandson of the wealthy elderly mans shows up and Mike and his wife (Amy Ryan) are forced to take care of the kid, Kyle (Alex Shaffer). Kyle, who ran away from his druggie mother, turns out to be a wrestling champion - a perfect fit for Mike's high school team. Kyle also has no idea that Mike is using the guardianship of his grandpa to get paid. Can we see an obvious future conflict?
Paul Giamatti is in almost every frame of this movie, which is a good thing because he excels at playing the convincingly (perhaps too convincingly) out of shape guy who is becoming increasingly frustrated with his income situation. And Amy Smart is good here as the strict yet good-hearted mother who is concerned for Kyle, which in another actresses hands could have easily become an annoying and overbearing character.
Vigman, Mike's assistant coach, is the supporting character who steals nearly every scene and generates most of the laughs. He is played by the hilariously serious Jeffrey Tambor. There is a scene at a wrestling match where Terry (Bobby Cannavale) shouts something inappropriate and Tambor closes his eyes in disbelief. It is the slightest of gestures yet the entire theater (including myself) nearly died laughing - it takes a skillful actor to do that.
Unfortunately, Bobby Cannavale's Terry is nowhere near as funny. It seems as if the script pushed all of its allegedly funny one-liners on Terry's character. The result is a few funny lines with double the amount of unfunny lines. It also did not help that, at times, Cannavele appeared to be trying to hard with his line delivery. There is nothing worse than when somebody tries to be funny.
That last tidbit about the acting in this movie goes to Alex Shaffer. This is his first movie and it shows in some scenes. While he satisfies at playing the silent and troubled teenager (aptly referenced to in this movie as the makings of a young Eminem), he is not at all convincing when he is required to yell. His "yelling" just sounds like the volume on his voice has increased - with no hint of actual anger.
If the acting in this movie ranges from very good to decent, the overall movie ends up somewhere in between. Win Win is a small movie and it knows it; it never tries to do anything surprising. The moment Giamatti's character makes the immoral decision there is a general formula applied to the movie that is never shaken off. Another possible flaw in the movie is that Mike and Terry are childhood best friends, and Terry is apparently rich; the question kept nagging at the back of my head: "Why doesn't Terry just help Mike out?".
There must have been some reason; probably because it may have taken away some of the drama from this dramatic comedy. Though even then, Win Win is not very dramatic nor does it have enough laughs to be a considered a comedy. If you are especially a fan of Paul Giamatti, Amy Ryan, and/or Jeffrey Tambor then you may really enjoy this. If not, it is still worth a watch but don't expect it to be anything memorable.
You can read ALL my reviews at JasonTheCritic.com