On its surface, Win it All, the latest collaboration between Joe Swansberg and Jake Johnson, is a straightforward retelling of the age-old story of a down-on-his-luck protagonist with a heart of gold. Directly below that, though, is a clever and charming exploration of human nature. Sure, it explores familiar territory, but it also toys with that territory and skirts outside of its boundaries, flirting with exiting it completely. This subversion of tropes and expectations elevates the film from a fun and enjoyable narrative to a clever examination of the human experience, mistakes and desires alike.
The film follows Eddie Garrett (Jake Johnson) as he struggles through adult decisions, continually hampered by his addiction to gambling. The first time Win it All subverts its narrative territory is when we follow Eddie into a gambling session. We expect to see him fail, we expect to see him spiral straight into the second act. But he doesn’t. He wins, he wins big. This is impressive narratively in a few ways. Most notably, it subverts expectations and engages the audience. Secondarily, it also effectively portrays why gambling addiction is so compelling and easy to fall into. That decision, then, is not only compelling, it is an effective character development moment. Things don’t stay sunny, though. Eddie loses his money, and much much more. This time the money he loses is not his own. He owes money, and he owes it to dangerous people.
As one could guess, this leads to a bit of a narrative pickle. But, instead of high concept hijinks the film settles into Eddie making adult decisions and trying to fix his life the proper, responsible way. Instead of going for one more big score to pay back the debt he owes, he gets a job, finds a girlfriend, and starts going to a support group. He is doing the right thing. Things are looking up for Eddie. This also subverts genre, and also gives the film the room to develop a compelling little character piece. A large part of the middle of the film has nothing to do with gambling, it has to do with Eddie and his life.
Win it All then does a strange thing, it subverts its own subversion and barrels back into a gambling thriller. Stakes unexpectedly raise, threats become real. The final scenes of gambling in Win it all are some of the most tense moments put on film. Thanks to the film slowing down to spend time with Eddie and his life, the threats he faces at the end are palpable for the audience. Unlike many films, we really care if Eddie succeeds. We want him to get out of his mess, we want his life to be okay. The climax then does something strange, Eddie makes the wrong decision for the right reason. This moment is touching, tense, and potentially devastating. This moment also, again, really humanizes and empathizes with the ease one can fall into addiction.
So while the synopsis of Win it all is correct, the film is really much more than that. It is an experiment of genre, toying with convention and tropes. It examines what kind of film you can make with this basic concept. The results are pretty astounding, Win it All both encapsulates and transcends its genre. The minds of Swanberg and Johnson have brought us something pretty special and we should all thank them for it.