Win It All is a comedy film directed by Joe Swanberg. The plot follows Eddie (Jake Johnson), a gambling addict who is tasked with looking after a bag full of money while an acquaintance is in the big house. Rather unsurprisingly Eddie gambles it all away. After reaching rock bottom Eddie realises he needs to get a real job and start trying to rebuild his life, this is all turned on its head when the guy he was watching the money for gets out early and wants his pay day; one last big score is needed.
Jake Johnson is an often-overlooked actor, he is a very versatile performer and this film proves it. His character is a very obvious slob/under achiever, but he is also far more nuanced than that, he is a broken man who wants to be well again, but the thrill of winning or losing big keeps dragging him back down the hole. He is both sympathetic, yet unlikeable. He is a complex character.
I enjoyed the film quite a bit, admittedly I am a Jake Johnson true believer, so I may be a bit bias. My one issue with it is that, despite telling a story grounded in reality, it feels very Hollywood. By that I mean the way things conveniently work out, things that wouldn’t happen in real life, it gets to a point where it is so unbelievable the drama loses no longer feels real.
Overall, an enjoyable watch, but one that almost becomes fascial towards the end.
Pros.
Jake Johnson
His character and performance
It is fun to watch
Cons.
The ending is absurd
Falls apart if you think about it too much.
3/5
Reviewed by Luke
Another Millennial Reviewer 