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"Win it All" SXSW Movie Review

Win It All SXSW Movie Review

Win it All
Photo courtesy of SXSW

Film is reviewed from the 2017 SXSW Film Festival screening

We first see Eddie (Jake Johnson) working the streets of Chicago as one of those flag guys that tries to get you to park in his parking lot. We see him get paid some cash by the lead worker and then Eddie heads to a neighborhood. There he goes down a back ally and nods to a guy hanging out by the back door. Eddie heads in, and we realize that this is an illegal gambling establishment. It's obvious that this is a second home for Eddie, that this is his element. We see him play various games while drinking the night away.

It is very evident that while Eddie thinks he is good a gambling, he is pretty bad. We can tell that by the end of the night, he has blown the money he just got paid for. He leaves the gambling establishment just as the sun is coming up. This is a routine that Eddie is used to, including the losing. Eddie knows he is a loser, you can see it in his body language as he heads home on the train. Waking up just before his stop he wearily heads down to his neighborhood. He goes into a local shop and tells the exasperated store owner that he is a little short and will pay him for the coffee and sandwich at the end of the week.

Win it All
Photo courtesy of SXSW

Eddie opens his apartment only to find a local gangster sitting at his breakfast table. Eddie is instantly worried that the gangster is there to collect an old debt, but instead, he has a proposition for Eddie. The gangster is about to serve 6 to 9 months in prison. If Eddie holds onto a duffle bag of the mobster, he will give Eddie 10,000 dollars as soon as the gangster gets out. His only conditions; Eddie does not look into the bag and does not tell anyone about it. Eddie decides that this is easy money and he agrees to keep the bag hidden. Eddie being Eddie, it's doubtful that he can keep his curiosity from looking into the bag and we all know what happened to the cat that was curious.

This is how the latest movie starts from the team that brought us the excellent Drinking Buddies (2013), Joe Swanberg and Jake Johnson. After whiffing on the too dark film Digging for Fire (2016), Johnson and Swanberg are back in the romantic comedy business, and it's right where they belong. The dialogue is sharp, quick and flowing, with the interaction of the characters is real and believable. There is an almost improvisation feel to the interaction between characters, with some of the best scenes of the film filled with the characters just interacting as their lives go on. The script does a great job of making the sad sack Eddie seem lovable; we want him to turn his life around and succeed. We just wonder if he is too stubborn to finally admit that he needs to change.

Win it All
Photo courtesy of SXSW

The heart of the film is the relationships that Eddie has in his life. He has a brother, Ron (Joe Lo Truglio), a family man who adores his brother but has been burned too many times by Eddie. Ron would love nothing more than for his brother to come to work at the family landscaping business. Eddie, like everything in his life, doesn't want to put in the hard work, he wants the easy score to make a living, and always thinks the next big one is right around the corner. Eddie also has a long-term relationship with his on again/off again gamblers anonymous sponsor (Keegan-Michael Key). The sponsor has also been burned by Eddie, so much so, that he is more amused by Eddie's troubles than worried about them. Lastly, Eddie has started a relationship with a nurse named Eve (Aislinn Derbez), who he meets by chance at Eddie's local dive bar. For the first time in his life, Eddie realizes that this is the woman that he could change for; the big question is, will he have the strength and fortitude to follow through?

I loved the performances in this film. Keegan-Michael Key is so much fun to watch as the put-upon counselor. Johnson and Key play off each other with great comedic ease. There are some real "brother-like" chemistry between Johnson and Truglio. You can feel the love the two characters have for each other on the screen, right along with his brother you are rooting for Eddie to clean up his act. There are some nice romantic sparks between Johnson and his love interest, played by the great Mexican actress, Aisling Derbez. Johnson allows us to see that Eddie knows that this woman is special and he can't mess this relationship up. Derbez is a delight to watch interact with Johnson as their characters go from flirtatious feelings to the knowledge that something serious could be happening between the two of them.

While most of the film is light-hearted, this is a dark undercurrent of how gambling can affect not only the lives of the gamblers, but also their family and friends. The film treats gambling for the disease that it is, though a lot of the comedic elements come from the same source. Johnson and Swanberg do a great job of not letting the comedic elements get too out of control, as well as not allowing the seriousness of gambling addiction to dominate the cinematic experience.

Win it All is a film that while the main character usually draws a bad hand, you get a winning feature that is both funny and moving to watch.    My Rating: Full Price

My movie rating system from Best to Worst: 1). I Would Pay to See it Again 2). Full Price 3). Bargain Matinee 4). Cable 5). You Would Have to Pay Me to See it Again

For more of Mike's reviews and interviews click here

For more information on the SXSW Film Festival go to

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