Win It All

Win It All is a 2017 drama-comedy film directed by Joe Swanberg and starring Jake Johnson, Rony Shemon, and Morgan Ng. The film follows the journey of a gambling addict, Eddie Garrett (Jake Johnson), who is given a bag of money to hold onto by an acquaintance leaving for jail, only to find that the money belongs to a dangerous criminal.

Eddie is initially hesitant to take the bag of money but eventually succumbs to the temptation of potentially winning big at the local casino. Despite his repeated attempts to resist temptation, Eddie spends the entire contents of the bag in a matter of days, losing not only the money but also his job and apartment.

Realizing that he has nothing and no one left, Eddie sets out to redeem himself by trying to win back the money before the criminal he owes comes looking for him. With the help of his brother Ron (Rony Shemon) and Ron’s adorable son, Eddie navigates the treacherous world of gambling, trying to beat the odds and win it all.

The movie is a character-driven story that explores the devastating effects of addiction and the lengths one will go to make up for their past mistakes. Jake Johnson, who also co-wrote the screenplay with Swanberg, delivers a compelling performance as Eddie, a man struggling to escape the throes of his addiction, while simultaneously finding some semblance of redemption. Johnson brings a nuanced and raw energy to his portrayal of Eddie, making the character more relatable and sympathetic, despite his flaws and bad decisions.

To make matters worse, Eddie is also grappling with a broken heart, following the end of a relationship with a woman named Eva (Aislinn Derbez) who had encouraged him to seek help for his addiction. In one standout scene, Eddie attends a Gamblers Anonymous meeting, where he struggles to articulate the source of his addiction, until he eventually breaks down in tears. Through this scene, Johnson captures the deep emotional pain and vulnerability of addiction, showing that it is not just a bad habit, but a disease that requires support and healing.

Alongside Johnson, Rony Shemon delivers an endearing performance as Eddie’s steady and supportive brother, Ron. Together, the two brothers have a natural chemistry that pays off in some of the film’s most touching moments, including a scene where Ron tries to teach Eddie how to play chess.

Despite being a relatively low-budget film with a simple storyline, Win It All manages to stay engaging and entertaining throughout, thanks to Swanberg’s direction and Johnson’s writing. The movie moves at a brisk pace, with plenty of tense gambling scenes and moments of levity, including a funny subplot involving Ron’s son and his obsession with putting together a dinosaur puzzle.

Overall, Win It All is a well-crafted film that offers a poignant and empathetic portrayal of addiction, while also delivering a satisfying and uplifting resolution. It’s a movie that will make you root for the underdog and walk away with a sense of hope, even in the face of seemingly insurmountable odds.