‘Win It All’ Is A Gamble That Doesn’t Pay Off | SXSW Film Review

Eddie Garrett is a mess. After bouncing around Chicago working dead-end jobs wherever he can, Eddie spends his nights looking for the ever-elusive ‘big score’ in random card games, losing every dollar he just earned. When a small-time gangster randomly shows up with an opportunity to make $10,000 simply by guarding a duffle bag until he’s released from the slammer, you can already see in Eddie’s eyes that this will quickly escalate into an explosion of bad choices. After yet another night of drunken shenanigans, Eddie kicks reason to the curb, opens the bag and discovers thousands of dollars inside. What could be a better idea than taking that cash and making a few bets in an attempt to Win It All?

Pretty much every plan would be an improvement, it turns out.

Jake Johnson stars as Eddie, and there are few actors better suited for a role like this. If you want us to root for a man who consistently sets his own life on fire, you need an actor we can instantly sympathize with. Johnson is an affable guy who is often the most memorable piece in many of his previous films, a regular Joe with a disarming everyman quality. Even as Eddie repeatedly discards his Gamblers Anonymous sponsor’s (Keegan-Michael Key) advice, we continue to believe in him just as we would our own personal friends who have made a cluster of their lives.

Eddie eventually finds Eva (Aislinn Derbez), a delightful nurse who refuses to suffer fools, even as she finds herself falling for one. Eva and her daughter is yet another nudging for Eddie to get his act together and finally ride the straight-and-narrow. After gambling away over $20,000 from the mystery bag, Eddie seems to understand and agrees to work a 9-5 for his brother, Ron (Joe Lo Truglio), who will take care of the debt IF Eddie can show him he has turned his life around.

Director Joe Swanberg reteams with his Drinking Buddies partner Johnson, and they come decidedly close to creating something memorable. Moments of despair are accentuated with bouts of levity as Eddie rises and falls on the highs and lows of winning. It’s his drug, a cathartic release. The problem is, he’s not very good at it.

As we careen towards the end of the film, Swanberg and Johnson repeatedly present Eddie as a guy no longer worth pulling for. He may be amusing and a party waiting to happen, but he’s also damaged goods. A guy who selfishly throws pain and regret back at anyone who gives him even a modicum of a chance at redemption. And when faced with the brutal truth of losing everything, Eddie is tossed a Titanic-sized cliché ending so generic that it literally affects every frame that came before it.

This is a difficult review to write, because at its core, Win It All is an entertaining film. It’s engaging, witty, and even charming at times. Unfortunately, when faced with all of its chips on the table and a wager hinging on that final bet, it finishes the game with a losing hand.