Win It All (2017)

When Win It All appeared on my Netflix recommendations, I was already leery. Keegan-Michael Key’s face smiled from the title card, promising another comedy starring the sketch comic. Already tricked by Teacher of the Year, also advertised on Netflix as starring Key, who turned out to be a side character, I did not expect the best from this film, despite the trailer heavily featuring him. It was even worse than with Teacher of the Year. Key’s character appears for at most ten minutes of the film, as the audience stand in, asking “What the hell is wrong with you, Eddie?” before leaving the real main character to his own devices. Stop doing that Netflix.

Jake Johnson plays Eddie, a gambling addict with no source of income. He bums money from his friends and family, while petulantly stating that he doesn’t want a job, because that’s not what he wants to do with his life. A likable protagonist he is not. No indication is given how he’s paying rent on his dingy apartment or even getting the money he keeps gambling with. One would imagine his friends would have stopped giving him cash long ago, much the way you would with a drug addict. At the start of the film, down on his luck, he is given a task. A local enforcer named Michael (José Antonio García) wants him to hang onto a bag of evidence while he does a quick stint in prison, after which Eddie will receive $10,000 as payment. Eddie’s curiosity gets the better of him, and he discovers that the bag is full of money. And so begins his downfall, sort of.



Eddie convinces himself that he will take $500 out of the bag to gamble with, and put it back after. And that sort of brings me to my biggest sticking point with the plot. The $500. He treats the $500 like a massive amount of money. Yet he’s clearly somehow paying rent on that apartment, and buying or borrowing enough food not to starve. He has a car, so it’s either paid off or he’s already making payments on it every month. He can afford gas. He has a cell phone with a working plan. But he has no job. Where is he getting the money to gamble? Why does he need to borrow that $500, when all of his expenses are apparently already covered, and a minimum wage job would give him more than that in two weeks? Maybe if it was a larger amount of money that he took, but by making it only $500, it raises a lot of questions about why he can’t make that kind of money anytime he wants. There’s no indication that he keeps getting fired from jobs, and his brother starts the movie offering him one. He has immediate access to an unskilled labor position that he can utilize whenever he wants for some quick cash, but we’re supposed to accept that he’d rather just steal the money from a criminal.

Amazingly, it works. He ends up with $2100 after his night of gambling. For some reason, he doesn’t put the money right back in the bag and lock it up. Probably because the movie would be over. The next night Eddie goes out on the town, living large and asking out Eva, played by Aislinn Derbez. The relationship isn’t terribly done, but it’s not well done either. It just sort of exists to make sure the movie isn’t under an hour long. Had we been given some indication that Eddie doesn’t have healthy relationships with women, it might have served a purpose to the main plot, but we don’t. So instead of “Eddie keeps himself together long enough to have a serious relationship”, we get “And then Eddie and Eva dated, just like every other couple on the planet”. The plotline culminates at the end of the movie with a pointless rising of pointless stakes where he misses dinner with her family… because he’s in the hospital. The conflict, if it can be called that, is solved by him saying “I was in the hospital”. There was literally no reason for it to exist.

But what about the main plot? Well Eddie goes out to gamble some more and loses $21,000 from the bag. Panicking, and after much soul searching, he humbles himself by getting a job at his brother’s landscaping company, deciding to finally, at forty, be an adult. And again this is portrayed as him giving up his on his values and humbling himself. Buddy, that ship sailed fifteen years ago. Ten if you’re generous. You’re a forty year old gambling addict with no job history. Nobody feels sorry for you. At this point, the movie starts becoming an almost interesting story of a forty year old failure turning his life around. His brother even agrees to pay off the debt in six months if Eddie sticks with the job and doesn’t gamble.

All goes well until Micheal calls to tell Eddie that he’s getting out of prison that Monday. Eddie is forced to take the duffel bag and enter a high stakes poker game to win the $20,000 he still needs to replace. We’re treated to a montage of Eddie losing and winning until he’s replaced all the money, and decides to keep going. Only a heart attack stops him from failing all over again. The movie ends with Eddie learning nothing, saving the day by doing exactly what got him in trouble in the first place, and only not digging himself into a deeper hole by a Deus Ex Machina. The whole middle of the movie, where we saw a broken failure of a man try to start his life at forty? Meaningless. Because he can always just gamble away any problems, then dig himself into a hole, then gamble out of that, then dig himself into another hole, and so on forever.