Review: Win It All

Win It All, the third collaboration between director Joe Swanberg and actor Jake Johnson, is as endearing and charming as its perpetually down-on-his-luck protagonist. Like his previous films, but particularly last year's Digging For Fire, Win It All suffuses a simple and often-seen narrative with a richly textured characters and an abundance of humanity. The result is a stealthily appealing and very satisfying viewing experience.

Johnson portrays thirty-something Chicagoan Eddie Garrett, who spends his days working odd jobs to finance his all-night poker sessions. After another losing streak, he arrives home one morning to find loan shark Michael (Jose Antonio Garcia) waiting for him. Terrified that he might have some body parts broken for not paying a debt, Eddie is relieved when Michael offers him a proposition: if Eddie can look after a duffel bag whilst Michael serves a six-to-nine-month prison term, then Michael will give him $10,000 upon his release. It's an offer too good to refuse but, when Eddie discovers the duffel is filled with piles of cash, a temptation that becomes too difficult to resist.

Much to his Gamblers Anonymous sponsor Gene's (Keegan-Michael Key) chagrin and amusement, Eddie hatches a doomed-from-the-start plan. What if, Eddie posits to Gene, he just takes $500 out of the bag and bets with it? He'll replace the $500, pocket the rest of his winnings and enjoy the happily ever after. "There's never been a happy ending for you," Gene points out after reminding him that he hasn't been to a meeting in six months. Yet Gene knows that Eddie won't heed his advice and the -$500 text that flashes on-screen soon increases, a horrifying marker of how deep a grave Eddie is digging for himself.

Overwhelmed with desperation, he reaches out to older brother Ron (Joe Lo Truglio), who's happy when Eddie finally agrees to take a job in the family's landscaping business. Things start looking up even more when Eddie meets Eva (Aislinn Debrez), a single mother and nurse with whom he shares an instant connection. Just when Eddie seems on the straight and narrow, he receives a call from Michael, who announces that he's getting an early release. Predictably, this sends Eddie on a rapid downward spiral.

Win It All is undoubtedly Swanberg's most refined and mature film to date, with a narrative accessibility that still retains the improvisational feel of his earlier work. There's an easiness to the film but at no point does Win It All feel trifling or innocuous. Though it maintains a lightly comic tone, Swanberg doesn't mask the violence that whispers on the periphery. Swanberg maintains an authenticity throughout - that, along with the wonderful chemistry between Johnson and Derbez as well as Johnson's brashly appealing performance, brings a fresh energy and perspective into an oft-told tale.

Win It All

Directed by: Joe Swanberg

Written by: Joe Swanberg, Jake Johnson

Starring: Jake Johnson, Aislinn Derbez, Joe Lo Truglio, Keegan-Michael Key, José Antonio García