It is said that art often imitates life and for me that is true, most of the time. I say most of the time because I think when it imitates the highs they are often too high, but the lows always seem right on target. It is those lows that I find sometime hard to watch. Like those moments when you see a character doing something that you know will not end well. You as a viewer know what is coming but all you can do is grin and bear it and take the ride with them.
Eddie (Jake Johnson) is one of those characters, and in “Win It All” there are a couple of times you want to reach through the screen grab him and scream, “What are you doing!?” Eddie you see is not ok, as he has a little gambling problem. And by little, I mean his life revolves around it, often staying out all-night and living on favors from people. Not wanting to change, Eddie is asked to do a favor for a friend, one you should never ask when you know that person has a gambling problem. Eddie is asked to watch some money. All he has to do to is sit on it and he will be ten thousand dollars richer, but things are never that easy. While it starts small, soon Eddie is borrowing to continue his losing ways, before long he is in way over his head, and in his words has ‘hit the bottom’. The question remains, is it too late and can Eddie dig himself out of the hole he put himself in?
“Win it All” is the latest collaboration between Jackson and writer/director Joe Swanberg, but they went about this one a little different. In their past films together, they relied heavily on improvisation, this one comes with a script, written by both Jackson and Swanberg. The story is one that has been told before, the gambler who reaches rock bottom and just when he gets there somehow finds a way to get out. Jackson is good, as playing a guy like this just feels right. Where the film starts to lose its way might be in the script, but this story needed one. It’s not a bad script or a bad movie at that, it really turns out to be a little above average. I know in the world of rating things a little above average doesn’t scream confidence, but “Win It All” is worth the watch. Another thing working for it is the good supporting cast, which is lead by Aislinn Derbez as well as Keegan-Michael Key and Joe Lo Truglio. “Win It All” is what you call a safe bet, while it may not blow you away, you can just let it ride and enjoy.