Review - ‘Win It All’ Is a Low-Stakes Table But a Good Time

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‘Win It All’ Is a Low-Stakes Table But a Good Time

Joe Swanberg’s latest character study combines neo-noir and lawnmowing.

I may be overly sympathetic towards Eddie (Win It All’s protagonist played by Jake Johnson) during the film’s opening credit sequence, because I recently took a similarly bleary-eyed train back home from Chicago’s Chinatown after a long night of cutting my losses. It’s not just that, though. Win It All is a slow-burn dramedy set on undercutting the romanticized, disheveled losers of noir while still developing a charm of its own. Johnson, in his expressive, frumpy portrayal of a low-stakes gambling addict – the kind of guy that wears a thin gold chain around his neck and really means it – finds pain, humor, and hope in a dead-end card junkie.

It helps that he co-wrote the screenplay with director and editor Joe Swanberg, who’s been his collaborator (in Drinking Buddies and Digging for Fire) in making character-focused slices of near-normal Americana. These are movies where the drama is almost completely relatable – stories you could hear at the bar while only saying “oh yeah right” once or twice. And to be fair, it’s not hard to buy Eddie. Eddie is addicted to losing, a fuck up and a “USDA Prime ribeye loser” as per his non-sponsor Gene (Keegan-Michael Key) from a failed run at GA. He’s the kind of person who’s ingrained the concept of the American Dream to the point of self-sabotage. No lessons learned; the world’s against him and his nagging put-together brother Ron (Joe Lo Truglio) is just another square.

So it makes sense to us that when his acquaintance Michael (Josè Antonio Garcia), who is heading to prison, offers to pay Eddie to watch his duffel bag during his sentence, of course he goes for it. To tip us off, two moviegoing senses get distinct warnings: we see Michael’s imposing neck tattoo and hear that he’s willing to pay Eddie ten grand to keep this away from the cops, no questions asked.

By this time, Swanberg and Johnson have us in their rhythm. Swanberg films things tight, handheld, and natural. Johnson plays an obsessive light on charm and long on sincerity, his outrageous facial expressions put to good use. We know Eddie, so of course we know he’s going to look in the bag, of course it’ll be full of money, and of course he’s going to lose it all. We know this, Gene knows this (and laughs in his face when it all comes true), and Eddie knows this. To make matters worse, he met Eva (Aislinn Derbez) on his post-duffel discovery high and – oh no – they actually hit it off. Now he has something to lose, though like any good gambler, his defeatist complex lives inside a shell that always professes an ability to win.

Swanberg has spent his recent career focusing on place, like in Win It All’s Chicago-set and Swanberg-helmed Netflix cousin Easy, dotting his urban landscapes with characters. Sometimes the loose amiability can cause the drama to lull – not quite like derailing a train, more the untethering of a listless boat – but when it hits, Swanberg’s love for his city transforms the alleyways and dive bars into expressionistic sets somehow hyper-real. Every shot of his fiction becomes something you could put on a charmingly dingy brochure whose accuracy is flattering only about half the time. The rest of the time it’s losers being told to grow up while simultaneously smoking a joint.

This hypocrisy is recognized, considered, and ignored. Eddie finds himself in a world that desperately wants to help him, but can’t seem to stop kicking him first. Or at least, that’s what he tells himself as he continues flushing the money away, only stopping to get a landscaping job once he’s in the hole for twice what was in the bag.

The film’s stakes remain surprisingly low, mounting his desperation for laughs at first with a cheeky graphic counter tabulating his debt, until the final half hour of the film. That’s when Eddie finds out that Michael’s being released early and he’s very excited to pick up his newly-emptied bag. The tragic excitement of “can he Rounders this shit?” quickly reinforces the weariness the film associates with addiction. If it were another movie, the jazz would fire up and the film’s fun-filled finale would kick into high gear. Instead, it’s a series of gut punches.

Win It All thankfully has a metered definition of “all,” because there’s no triumph in it. No Robin Hoodery. Only a small man with small goals who is haunted, like us, with the aching feeling that this threat, the out-of-control confidence of a purist loser, will always be there no matter how normal his life becomes, waiting to spring invisible and deadly like a heart attack.

Jacob Oller writes everywhere (Vanity Fair, The Guardian, Playboy, FSR, Paste, etc.) about everything that matters (film, TV, video games, memes, life).