Movie Review – Win It All (2017)

Life’s just one big gamble, 3.5 readers.

BQB here with a review of Netflix’s “Win It All.”

I caught this film by accident, scrolling through Netflix’s never-ending list of offerings when all of a sudden, the premise just appealed to me.  It’s simple and from a writer’s perspective, simple is good.  Simple isn’t necessarily easy but sometimes simple doesn’t need you to keep a variety of plates spinning in the air the way more complex films do.

Eddie (Jake Johnson) is a down on his luck, degenerate gambler.  His only source of income comes from his lowly job as a parking lot attendant (but only when the Cubs are doing well and fans need spillover parking.)

Addict that he is, his life is in a downward spiral, largely because whatever money he is lucky enough to get his hands on, he immediately takes it to an underground casino club to gamble it all away.

On one fateful night, a rather scary looking loan shark who Eddie has tangled with in the past makes an offer.  He’s been sentenced to relatively short prison sentence and wants Eddie to hold onto a bag of money, no questions asked.  Keep the dough safe and at the end of the bid, 9 months to a year tops, the crook will reward Eddie with 10,000 bucks.

I know.  It is a rather gaping plot hole that anyone would trust a degenerate gambler with any sum of money, but then again, the loan shark may not have a large number of trustworthy people to turn to and frankly, his menacing appearance would be enough for most people to avoid screwing with him but alas, Eddie’s addiction is that severe.

Long story short, Eddie gambles away a large chunk of ill-gotten loot, and as you might imagine, the rest of the film circles around Eddie’s various attempts to get himself out of hot water.

The middle of the film has a nice message.  SPOILER ALERT, at that point, Eddie has lost a large sum yet it isn’t an insurmountable amount.  He works out a deal with his brother to take a job with the family landscaping business, and he devotes as much as he can from each paycheck towards refilling the bag of money.

In doing so, Eddie starts to feel good about himself.  He’s doing productive work.  He’s achieving goals.  His confidence soars, so much so that he meets a nice woman.  Suddenly, he’s got a job, a girlfriend, reasons for being…what a turn around.

I assume the message there is that when it comes to anything good in life, the long game always beats the short one.  You’ll get better health through daily exercise than you will through a one-time sip of that snake oil supplement you saw advertised on late night TV.  You’ll find a more meaningful relationship through a longtime partner than you will with a one night stand.  And while your paycheck doesn’t seem like much, save enough over a long period of time and you’ll get somewhere.

Alas, SPOILER ALERT AGAIN, shenanigans ensue, Eddie can’t beat his addiction and like the alcoholic who can’t shake the booze, he keeps dipping his hand into that bag and keeps losing, and losing and losing.  Like the fast food addict who knows his love of Big Macs will eventually lead to a coronary, Eddie knows that pissing away a murderous criminal’s cash is going to wind up with him six feet under but sadly, that addiction is calling and hey, surely there’s enough time to turn it all around before that inevitable bad ending right?  Come on, just feed the addiction beast one last time, ok and another last time, and one more time…just two or three or twenty last times, tops and then let’s quit cold turkey tomorrow.

I don’t want to give away the ending but there was a part of me that thought it might have defied the typical gambling movie genre by letting Eddie beat his addiction through that “build yourself up from the rock bottom day by day” routine we all hope to master.  Ironically, Eddie beats his addiction by feeding his addiction and while it made for fun viewing, I’m not sure that’s the best message for addicts out there.

Comedian Keegan Michael Key stars as Eddie’s sponsor or at least, friend, because as he notes, sponsors can only help recovering gamblers who are working the program steps and Eddie isn’t, at least at the film’s beginning.

Overall, I enjoyed this movie.  My main critique is that in many ways, it comes across as a shoddy student film.  There are many parts where the dialogue seems improvised and wrap ups of plot points seem thin but I on the whole, I liked it and I think it did have a good message, i.e. the constant ware we all face between instant gratification (do the bad thing that gives us a tiny bit of happiness right NOW and who gives a shit if it fucks up our future later) vs. forcing ourselves to be that little turtle.  He’s slow.  He’s steady.  Progress towards a happier you seems like it is taking forever and will never happen but years later, you look around and you see yourself with a nice house, a great job, a loving family and you’re happy you took the time to solve this puzzle, one little piece at a time.

STATUS: Shelf-worthy.

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