Win it All is a 2017 release available now on Netflix, directed by Joe Swanberg starring Jake Johnson and written by both of them. Coming into the movie I was familiar with Swanberg's first movie "Drinking Buddies" which was unique in that the dialogue in it was completely improvised. "Win It All" however is not improvised but the dialogue is very well written and the actors are good enough that it definitely seems very natural and at times I thought it was also improvised. The movie also looks very good, very stylish, it has this grainy look that makes it look very different from most movies out there. That's about where the positives for this movie end.
I guess that's a bit harsh, it's not that it's a bad movie per se. It's that it's an unfulfilling movie. The actors are good, the performances are good, the dialogue is mostly good, there's some very real moments in it but ultimately the movie doesn't go anywhere. It's a movie about a gambling addict who is given the task of taking care of a huge amount of money for a seemingly dangerous guy while the dangerous guy is in prison, how could that NOT be compelling yet the movie fails because there's no real consequence to anything in it.
That's my real problem with the movie I guess and it's a problem I have with many movies. Even in "slice of life" movies like "Everybody Wants Some" where "nothing happens" THINGS happen. Characters learn things about themselves or others, there's moments of growth moments where we as the viewer can see lessons we've learned reflected in the characters actions and that's what makes those movies work. In "Win it All" there is nothing like this, even Eddie's bottom isn't really all that compelling, it just made me go "well yeah.." and the resolution of the movie was wholly unsatisfying. It also happens so quickly and so suddenly that as a viewer it barely gives you enough time to assimilate what really just happened.
I'm trying to keep this spoiler free, because I don't think many people who read this would have seen it but We sit through two hours of a like able loser douchey kinda guy with a gambling problem who at the end of the movie is still in the same situation as the beginning of the movie except now he's met a girl. There's no evidence of real growth. There's no change. "Win It All" is exactly like its main character, it's charming, cool and a little bit funny but it's ultimately a bit of a loser.