Movie Monday: ‘Win It All’

Movie Monday: Film Recommendations By Our Contributors

When you hear someone list their favourite films to a friend, or you do so yourself, the answers vary. They all fall along the same lines; prestige dramas of Academy Award-winning renown, nostalgic children’s favourites, and perhaps the latest film by a new indie darling director. Rarely will you see someone pick out a low-budget Netflix movie starring Jake Johnson (New Girl), and yet here we are.

In its brisk 90-minute runtime, Win It All tells the story of Eddie Garrett (Johnson), a loveable loser who can’t stay out of his own way, drinking and gambling his way to an early grave. When a friend gives him a duffle bag of cash before heading into prison for nine months, promising $10,000 in return come the end of his sentence, our perennial loser can’t help but use the money to try and increase his own fortunes, with dire consequences. Faced with running, leaving behind his new and, more importantly, normal relationship with Eva (Aislinn Derbez), Eddie plays the ultimate gamble and takes the biggest risk, in the hope that he can win it all.

There’s so much about this little Netflix movie that you’ve never heard of that speaks to me, and so much that speaks to my own battles with addiction and self-destruction. That inability to just stop being your worst enemy. Gambling, as in Win It All, was never my vice of choice. Mine lay more in a glass of wine, a pint after work, a round of shots with strangers at three o’clock in the morning when you have work just a few short hours later. Always just one more round, no matter the cost. Just as for Eddie, there was always one more hand of Texas Hold ‘Em to play, consequences be damned.

And yet for Eddie, just like myself, it was never for a lack of support. His sponsor Gene (Keegan-Michael Key) is a constant presence, encouraging Eddie to seek help. His elder brother Ron (Joe Lo Truglio) runs the family business and repeatedly offers Eddie the chance to make something of his life. But they’re all tired of and frustrated by Eddie, who will happily take one step forward, but can’t help himself from following that with two steps back. When I had my struggles, I had incredible support around me, with friends and relatives constantly offering their concern and encouragement. I’d listen. I’d nod. I’d agree with what they were saying. Then I’d have a drink later that night, forgetting all about it. Whenever films tackle these themes, I’ve often found them to be somewhat elevated. They don’t necessarily seem grounded in a lived experience. Take Flight, for example. An undoubtedly excellent film led by Denzel Washington as an alcoholic airline pilot, but one that feels slightly ‘Hollywood’ in its depiction. It’s dramatic, and addiction rarely is. What Johnson and director/co-writer Joe Swanberg have created is an everyman, strikingly real, and very human depiction of destructive dependency. Win It All enabled me to feel seen. It enabled me to seek help.

It’s in this everyman that Win It All also finds its immense charm. Anyone familiar with New Girl will recognise Jake Johnson’s gift for physical comedy and endearing himself to the audience. In Win It All, when thrust front and centre, he thrives. Whether it’s sat round a table damning his own luck as he calls for more poker chips, gazing off into the distance as the thunderclouds roll in and the horse races are cancelled, or as he learns how to rake. It doesn’t matter. We are eternally invested in this character, flaws and all. Behind the scowls and the exclamations of innocence, there’s a pathos to Eddie that pulls us towards him. We can’t help but root for him. To hope that he overcomes, eventually, the demons he is facing.

Removing all personal feelings, ever so briefly, Win It All is still a special film. It’s lit and shot with a grainy quality that reminds you of its low-budget origins. It boasts a score of pure simplicity; pounding drum beats that get faster and harder, matching the pounding of Eddie’s heart as he barrels towards disaster. It’s witty and charming, sprinkled with a very human romance. The dialogue is realist too, never feeling like a script. There’s a natural quality to conversation in Win It All, reminiscent of the nonsense you chat with your friends when you’re all out together, or the awkward speech that comes out when you first talk to the girl you like. In a world of perfectly crafted, tight scripts, the human chaos of Win It All shines through.

The craft isn’t how I want to remember Win It All though, despite the ability on display. We love movies because they are personal to us. They reach inside of us, eliciting emotion that few other art forms can conjure. Win It All is one of those special movies for me. For better or worse. That point still stands, but it needs an addendum. Win It All reminds you that one day, even if you feel like an eternal screw-up, you might just deserve that good thing that comes your way.

Words by Jack Francis

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