Joe Swanberg and Jake Johnson team up again to create Win It All, a story about a gambling addict whose inability to separate himself from losing makes life incredibly difficult. When one of Eddie’s (Jake Johnson) acquaintances is headed to prison for six months, he asks that Eddie look over a duffle bag for him. Eddie is promised a payment of $10,000 at the end of the six month period as long as no one (including himself) touches the contents of the bag. Curiosity gets the better of him and Eddie realizes that the bag contains $50,000. Eddie makes it his mission to use some of that money to make a little cash on the side. When he finds most of the money gone, he decides that he needs to begin working for his brother in order to earn it all back before it is too late. In the process of all of this madness Eddie meets a woman, Eva (Aislinn Derbez), and begins to fall for her. His poor decision making has led him to a dark place, and he must find a way out before he puts himself and his loved ones in danger.
Jake Johnson is known for being a funny guy. He brings many levels of comedy to the table, and his acting ability often allows him the opportunity to deliver on his comedic endeavors. His role in Win It All is to portray a down-on-his-luck gambling addict, and his approach to comedy here is incredibly dry (making it unappealing to some). Johnson has a lot of experience, and has found great success in the past (particularly in the FOX comedy New Girl), but Johnson’s ability to effectively deliver comedy in this film falls short. His acting is still wonderful, but it seems that he, and Swanberg, have written him into a corner. The unfortunate writing causes his character not to be as funny as audiences might hope. His story is interesting and audiences find ways to relate to the character (even on the simplest of levels), allowing those audiences to appreciate what is in front of them, and film as a whole. While he struggles comedically, his wonderfully strong acting ability, paired with Hollywood newcomer Derbez, finds ways to appeal to audiences on an emotional level. Due to the fact that Eddie’s life is in such shambles, his ability to create a positive relationship with someone prods audiences’ hearts and allows them to feel something. Their relationship is so beautifully simplistic and innocent that audiences are able to connect on a deeply emotional level.
A seemingly random casting choice (only due to the fact that the film appears to be incredibly low budget) is Keegan-Michael Key (Gene). With the exception of Johnson, no one in Win It All has made it big yet. His presence in the film makes portions of it more enjoyable than the rest. He has the ability, better than most, to reach audiences of all comedic calibers and make them laugh. He plays off of Jake Johnson so well that one might assume they have worked together for years. He is beautifully gifted in the art of acting, and, as previously mentioned, just his presence is enough to turn audiences on to the film.
As Win It All moves toward its close, viewers are immersed in a scene of extreme gambling that makes even those viewers uncomfortable. Swanberg focuses on the clicking of the poker chips, the clink of the ice and the deep, slow breaths of the card players. This scene is an example of directing at its best. Audiences are forced to focus on what is taking place, rather than being distracted by deep meaningful acting or intriguing music. Swanberg is able to break this scene down to the bare minimum and leave audiences to listen and absorb everything on screen.
Even with all of the positives, Win It All manages to leave an inexplicable void in viewers. Something about the story feels incomplete and underdeveloped. There are so many positives, including acting from Johnson, Derbez and the supporting cast, intensely entertaining scenes about gambling addiction and enough suspense not to overshadow the light and subtle comedy. It touches on some difficult scenarios that a good portion of the population has dealt with, and the budding relationship between Eddie and Eva is truly adorable. With the exception of the unnerving feeling that Win It All is incomplete in some way, it is a low-key hit.
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