Win It All is the latest Joe Swanberg film starring Jake Johnson as a struggling gambling addict named Eddie. Faced with the opportunity to make $10,000 dollars by holding a bag for someone, he is too tempted and has to look what is in it. When he does, he discovers it is full of money, which he uses to try to get some extra cash. He heads to a local casino where he quickly turns $500 into $2,100.
After experiencing a high from winning, Eddie heads to a local bar where he meets Eva (Aislinn Derbez) and the two really hit it off. With so much going right in his life, Eddie attempts to press his luck further, which only leads too much bigger problems. He turns to his sponsor, played by Keegan Michael Key and his brother, Ron (Joe Lo Truglio) for advice. Searching for a solution, he stops gambling and starts to get his life in order only to be thrown off when the person for whom he is holding the bag decides to return in just a short week. He must come up with a solution or flee.
The performances in the film are great. The characters are entertaining, real and seemed to be second nature to the actors. They felt very natural in their roles. The chemistry was on point, which added to the even more to create engaging characters. Keegan Michael Key and Jake Johnson have some of the best scenes that really get the audience going. Jake has perfect timing and line delivery and really was a crowd pleaser.
Jake’s performance really kept the entire audience engaged and rooting for his character. All the laughs hit hard and where they should have. It was a well-oiled machine that was more than a joy to watch. The audience was having a great time, laughing with the jokes, and expressing horror as his debt continued to rise. The writing in the film was sharp and witty, which further prove that Joe Swanberg and Jake Johnson are a perfect match together and create great films.
While a lot of the film was funny, it certainly had its dark moments. It showed the harrowing reality of addiction and how you can truly lose it all at any point. The drama and comedy was perfectly balanced and extremely entertaining. Joe Swanberg is at his finest with Win It All.