Win Win is a complicated comedy that isn’t afraid to be challenging while making you laugh. It isn’t super heavy but it has a lot more weight than other recent indy comedies like Cedar Rapids.

Mike Flaherty (Paul Giamatti) is a struggling small town lawyer with a private practice who moonlights as a wrestling coach for a terrible high school team. Mike’s practice is failing and desperation is starting to set in when one of his clients, Leo (Burt Young), is faced with state mandated transfer to a nursing home. Mike sees an opportunity and finagles the judge to appoint him the man’s guardian so he will get the $1,500 monthly checks for his care…and then Mike moves him into a nursing home anyway. No one is the wiser and Mike can make ends meet so he feels it is no big deal. Then Leo’s grandson Kyle (Alex Shaffer) shows up and everything gets a lot more complicated. Displaced because his mom is in rehab, Kyle has nowhere to go and ends up staying with Mike. Things look pretty good when Kyle turns out to be incredible at wrestling but of course they don’t stay that way.

Win Win has a lot of funny moments. They aren’t big moments generally and you aren’t getting a lot of deep belly laughs but it is consistently funny from beginning to end. A lot of this comes from the chemistry between Mike and his assistant coaches Terry (Bobby Cannavale) and Stephen (Jeffrey Tambor) which is pitch perfect. While the comedy aspects are good and hit more often than they miss, what really sells Win Win is the drama aspect and the moral conundrum that crops up as a result of Mike’s desperation.

The writing in Win Win is very strong not just for the funny dialogue or well written emotional scenes but also just how it all plays out. Win Win impressively avoids a lot of the cliches you typically get in these sorts of movies while at the same time keeping things solidly grounded in reality. One example of this is Kyle’s wrestling. It is something that serves the story as opposed to dominating it and the affection that grows between Mike and his family and Kyle is real affection and not just based on his ability to win wrestling matches. Kyle himself isn’t content to be the star all by himself and actively works to help other members of the team improve. This improvement isn’t meteoric and doesn’t take them from losers to champs in a montage but he helps them believe in themselves more and feel better about what they are doing which allows them to perform better. I am very glad it avoided the Teen Wolf ‘now we are suddenly badass because I’ve learned my lesson about being a werewolf in high school sports (although I suppose that specific device would feel pretty out of place here given the absence of werewolves)’ and that the emphasis here is the overall story, not just the wrestling subplot.

The best thing going here is the sticky moral issues that form the backbone of the picture. Mike isn’t doing anything illegal really but he knows that Leo wants to live at home and has enough money to do so but Mike needs extra income and doesn’t have the time to directly care for Leo. He takes in Kyle and develops affection for him, helping the boy grow into a stronger person and to become more successful without any real expectation of reward (outside of winning wrestling matches) but is that enough to balance out karma for unethical behavior? The third act conflict really explores this issue without being heavy handed or melodramatic and resolves in a satisfying way for the viewer that doesn’t let Mike off the hook but also doesn’t make you feel cheated. It again also avoids cliches in this sort of movie and gives us something that works and feels right.

The performances are very strong. Paul Giamatti is reliable as ever and shoulders the weight of responsibility silently while putting a bright face on to his family. Amy Ryan does a great job as Mike’s wife Jackie who is at turns incredulous, frightened, angry and supportive all without feeling like there is any real acting going on. She and Giamatti have a strong rapport and you can believe that they have been married for years. Tambor and Cannavale were mentioned earlier and were excellent, but the real story is new comer Alex Shaffer. Shaffer is effortless here and while some might argue it is because he is generally acting disaffected most of the time, he stretches a lot more than that and delivers a touching performance that shows more layers than you might think at first.

Conclusion [9.0 out of 10]

Win Win is a great film that offers more than cheap laughs and a paper thin story. There are real moral questions asked here and the answers are just as complicated as the questions. The performances are uniformly good and the writing is tight and effective. It might move a bit slow for audiences expecting some kind of raucous Hangover style comedy but if you are looking for something with laughs that goes a bit deeper you could do much worse than Win Win.