“Win It All” did just that. Of all of the movies I was fortunate enough to see on screen at SXSW 2017, this was my favorite. It was filmed in my old neighborhood in Chicago and focused on a small-time degenerate gambler, which I used to identify as. It captured the essence of both perfectly. The shots of the parking around Wrigley Field that opened the film reminded me of the cost and frustration. While other movies have tried to show what back alley casinos looked like, Swanberg created a scene directly out of my late drunken nights.
While the setting was familiar, so were those involved. This was the fourth collaboration between director Joe Swanberg and lead Jake Johnson. Practice makes perfect, as the dialogue and pacing were sharp, never leaving a lull or dull moment. During the Q&A after the screening, the cast revealed that the script was heavily improvised. This created a natural communication that made you wrap yourself in the story immediately. While improvisation can be risky, the gamble paid off. The acting, direction and soundtrack are all tight, keeping you invested for every scene.
Eddie (Jake Johnson), a small-time gambler, is the quintessential loser. He takes short-term low paying jobs to support his gambling habit. You know he has a good heart and you want him to win, but he never does. Eddie is given the opportunity to hold a bag for a criminal/loan shark he knows while he has to do a short stint in jail. Of course, he opens it and discovers the cash inside. He goes to seek the advice of his Gamblers Anonymous sponsor, Keegan-Michael Key, and you know it won’t go as planned. He uses some of the money to go to the local underground casino and actually wins! On his high, he takes his buddies out for drinks and meets a nurse, Eva (played by Aislinn Derbez in her first American film role).
Aislinn’s accent perfectly captured the ones I used to hear everyday. The fact that there was so much improv in her second language proved her acting chops. The attraction between them feels real and life is good. Until that itch has Eddie diggin in the bag again. This time, the hole he digs himself gets deeper and deeper. Instead of going to his brother to bail him out again, he takes his brother’s job offer and works for the family business to get the money back. His resolve is tested, and his hard work starts paying off, until he finds out that owner of the bag is being released from jail early. Keegan-Michael Key is his last stop to figure out what to do. Like every good sponsor, he helps by giving him the information on a big poker game in the suburbs. Eddie takes what is left in the bag and risks everything. Can he win it all?
You can find out the answer by watching this movie. It has already been picked up by Netflix and should be released later this summer. You will be entertained. I’d bet on it.
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Update: “Win It All” is available to stream on Netflix on April 7, 2017.