It’s easy to see why Joe Swanberg found his muse in Jake Johnson. Both share a Northside Chicago upbringing, an affinity to dive bar drinking, and collaborative artistic endeavors. The two reunite for a third time in Win It All, an enjoyable character study of a compulsive Chicago gambler. As a Chicago native, I have several questions about how much time Joe Swanberg has spent in Chinatown underground gambling dens, and where the best bang for the buck location is in the city.
Eddie (Johnson) lives and dies by his obsession over high stakes gambling. He lives a grimy week to week existence, adamantly refusing a landscaping job from his brother Ron (Joe Lo Truglio) who wants him to stabilize. After a particularly terrible night where Eddie gambles away a con’s money he was “watching only,” Eddie decides enough is enough, and accepts the job from Ron. He also starts trying to clean himself up; his sponsor Gene (Keegan Michael Key) encourages Eddie to return to rehab. And after a particularly good day, our gambler meets Eva (Aislinn Derbez) at his favorite bar, and instantly the two strike up a very sweet connection. Eddie starts to realize this new life might actually be worth it, but ghosts of his gambling past come back to threaten this new life Eddie so wants to embark upon.
Joe Swanberg likes to subvert expectations and laser focus on a character or a few characters when he crafts his movies, partially for budgetary reasons, partially because it makes it easier to forge a connection to the character for the audience. For movies about gamblers, the gambling is usually magnetic and takes center stage because the stakes are so high. Swanberg purposely makes the gambling scenes seedy and grimy, perhaps to show the reality of a gambler who can’t even play in real casinos. For Swanberg, this story is not of gambling, but a spin on the addiction story. This creates a stakes struggle for the director, since we go from the roller coaster of gambling to forgetting gasoline so a mower can be used, setting back the day’s work. Swanberg does the best he can to connect us to Eddie’s struggle; I’ll admit it can be boring at times, but I did end up caring about what happens to Eddie and the people he loves, even though at times it can be boring and cliché driven.
A big contributor to the success of Win It All is the cast. Mr. Johnson continues to show why he is one of the more talented actors in Hollywood today. He’s almost the opposite of his New Girl character; Johnson makes Eddie as realistic as his other Swanberg characters. You feel like you’re watching your normal weird friend or family member who sometimes hits you up for money, and then you’re stunned to see in a Subway or AT&T shirt doing the day to day grind, a testament to Jake Johnson’s talent. Keegan Michael Key gives the movie a necessary jolt of electricity as Eddie’s sponsor, throwing grounded jokes effortlessly. Joe Lo Truglio was a surprise; usually he plays a creep or lacky, and here he’s fun as the grounded brother of Eddie. His bit about the gasoline is one of the best parts of the movie. Aislinn Derbez is the weak link here, clearly playing Swanberg’s version of the manic pixie dream girl. I’ve seen her in other Swanberg material and she’s great in it, so most of this I’m pretty sure is not her fault, but she’s just not as interesting as her male counterparts, sadly.
Win It All aspires to be a more noble Rounders. However, Rounders connects to what makes gambling fun and compelling, and Win It All is more interested in showing the darkside of its addictive nature. Maybe if Keegan Michael Key were playing Edward Norton playing Worm, Win It All would have been super interesting, but with Key’s improvising prowess, he would have turned Worm into Tyler Durden, and then the movie just goes off the rails.