7.5/10 As someone who is pretty neutral on the overall filmography (from what I have seen) from writer/director Joe Swanberg, I had mediocre expectations that this would be a fine but ultimately forgettable/average movie. I am always happy to admit when I am wrong and in the case of “Win It All”, I turned out to be gleefully wrong. While not ground breaking or Earth shattering by any means, this film takes a somewhat familiar premise but makes it extremely intimate and personal. All the more impressive is that Swanberg is able to accomplish all of this in an hour and a half with great pacing that never slows down for a second. As only the second film (and most recent) that lead actor Jake Johnson has written (he co-wrote this with Swanberg), I would like to see him do some more screenwriting. At the beginning of the film I was a little worried that Johnson’s lead character was going to be too unlikable for a protagonist (Johnson has definitely played some annoying, unlikeable characters before coughTheMummycough) and that the film would retread many of the same plot beats that other gambling/addiction films have already covered before. While Johnson’s character is rather annoying at the beginning, we get to see his character grow, get properly developed and have a wonderful character arc. The female lead and romantic interest played by Aislinn Derbez not only delivers a heartfelt performance but adds an additional layer of warmth to the film. Finally, Keegan-Michael Key and Joe Lo Truglio both play small but pivotal roles and where as in most films/shows they are both very over the top, their work is grounded and refreshing here. The film isn’t perfect and I wish some of the supporting characters would have been slightly more fleshed out. There is also a medical emergency moment that happens late into the film that feels out of place and unrealistic. As a nitpick, Johnson begins a job in the film and the boss tells him he will be working seven days a week. Roughly 15 or 20 minutes later, that same boss tells Johnson to have a great weekend and that he will see him on Monday. So suddenly he was working a normal, five-day work week with no explanation which was inconsistent. That was a very minor flaw but I still noticed it. Besides some minor issues, this is probably Swanberg’s best film out of all of his films that I have seen. If you are looking for a quick watch of something that may have slipped past your radar when it was initially released a few years ago, “Win It All” is a winning choice if you’ll take a gamble on it.
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