Win It All is a Netflix comedy special written by Joe Swanberg and the star himself, Jake Johnson. It has a funny beginning where, Eddie played by Jake Johnson, has a gambling addiction and is given a bag to watch for 6 months by a prisoner friend. He’ll get $10k for holding it, but he can’t look inside. Of course he does and it is full of cash, which he uses to gamble. The rest of the movie has a sort of somber feeling as Eddie wastes the money on gambling and has to find ways to repay it. In the process he goes back to work and gets his life on track and falls in love. The acting was great and it was somberly entertaining the whole way through. 

Here’s the trailer…


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