Win Win doesn’t really have a main plot. It has several small subplots that work together to form somewhat of a story. A few of the subplots don’t go anywhere. For example, the old boiler never gets repaired and never gets mentioned again after the first act of the movie, although the knocking noise still makes several appearances later on.
Despite the excessive foul language, and the way everything seems to get nicely patched up just in time for the ending, overall, it’s a great film that easily made its way into my top 20 favorite movies.
Where Win Win really shines is with its characters. Kyle is the coolest teenager ever depicted on film, always willing to help anyone without ever coming across as patronizing or “too nice”. Leo manages to be funny without it feeling like you’re laughing at his dementia. Stemler is the perfect level of annoying. Every character drew you in and made you care about what was going on, even if, at times, it wasn’t very much.
After all, isn’t that what movies are supposed to do?
Win Win didn’t break any ground visually. It kept things pretty low-key, and, at the same time, avoided the stereotypical look and feel of an indie film.
If it wasn’t for product placement, this movie would have been my first perfectly-scored movie. But, sadly, they just had to focus a little too much on Wii and Star Wars. Sure, Stemler was supposed to be a geek, but there are way more ways to be a geek than just by liking Star Wars and talking about Jedis and whatever.
Ever since I watched this movie for the first time a few months ago, Win Win immediately comes to mind whenever someone asks me what a good movie to watch is. At the time of this writing, I’ve only seen it twice, but I plan on watching it many, many more times in the future.