Win It All Review

Win It All fluctuates the highs and lows of Joe Swanberg’s cinematic lyricism (indie and simplistic), but smartly pushes all-in at the right moments. Dramatic beats are so in-tune with the gambler’s lament in this pursuit of mega-buck paydays that are always “right around the corner.” It’s more than just an addiction, though. The gambler is someone who becomes accustomed to losing, because risk and reward go hand-in-hand. Adrenaline spikes even when cash flows outward, because there’s always a chance for redemption. Taking down a massive pot with pocket Aces makes you feel invincible until your full-house gets busted by quads – trust me. Then it’s doubt, self-depreciation and another stack of chips that are going to turn your life around until they vanish, too.

Jake Johnson stars as Eddie Garrett, a gambling man who spends his days parking cars and nights shuffling cards. He’s a fixture at a local underground casino, where beers flow just a bit quicker than his bank account. Brother Ron (Joe Lo Truglio) desperately wants him to join the family landscaping business, but Eddie loves his “freedom” too much. He’s always on the cusp of new beginnings (so he convinces himself), but just needs a bit more capital – enter Michael (José Antonio García). If Eddie can safely stash a mysterious bag for 6-9 months (Michael’s prison sentence), he’ll be rewarded with $10K no questions asked. No brainer, right? Of course! Until Eddie discovers a large nest-egg in the zipped duffel. This is it. The cash Eddie so desperately needed to begin an epic winning streak. He’ll just take a chunk, keep his winnings and Michael will never know.

That’s before $27K is blown. 

Swanberg’s biggest achievement is exposing Eddie’s addiction without heaps of drama, because this is how a gambler typically operates. There’s no breakdown on a sidewalk or massive epiphanies. A gambler will simply lose, make excuses, set back out and lose again. It’s never an “issue,” per se. Win It All tones down Hollywood exposition and channels a true, human set of qualities that come and go without stormy thunders. Within a night, tens of thousands of dollars are gone in a blink. No slow-motion montage or inner narrative. Walk into a casino holding cash, walk out with nothing. Even Swanberg’s editing cuts help drive this notion, cuing the film’s heartbeat to more than a charismatic leading performance.

Who better to play a down-on-his-luck bum than Mr. Self-Abuse himself, Jake Johnson? Eddie Garrett has become addicted to excuses, self-loathing and all the negativity that comes along with being a loser. He starts each day by owing a local Bodgea man for coffee, and goes about a bar-stumbling existence that skirts any and all responsibility. The way he tells stories about being “up $200” before tumbling back down is descriptive, but better material plays out when wasting sponsor Gene’s (Keegan Michael-Key) time. “You’re my sponsor! You only hear about the bad stories! Most are winning stories!” As a Texas Hold-Em shooter myself, I found it easy to connect with Eddie Garrett because those are the same stories I once told (less stakes, less severity though). Johnson is so starry-eyed and beaten-down at the same time, making for a pitch-perfect fit into Swanberg’s tale.

Yet, this is a happy endeavor. Despite the criminals, monetary pitfalls and general malaise, Win it All is about that big, fist-pumping victory. In this case, it’s Eddie leaving his dead-end lifestyle behind for something more fulfilling. Joe Lo Truglio pushes towards reform as his preachy but still loving brother, and Aislinn Derbez offers stability as love interest Eva. A light goes off in Eddie that Johnson navigates with up-beat enthusiasm, even though his methods of re-filling Michael’s bag reach rock-bottom desperation. That’s when Keegan Michael-Key gets this movie-defining moment where Gene laughs in Eddie’s face after hearing how seriously the situation has become. Johnson sits there, stone faced and pleading, while Michael-Key cackles incessantly like someone’s life isn’t in danger. Swanberg so handily captures the human experience, off-color reactions and all.

If you’ve seen a Joe Swanberg film, you’d seen them all (in theory). This is either a beautiful revelation or slight deterrent. Win It All is no different, as it fits snugly into a catalog of independent cinema that frames real, forlorn characters who struggle to find direction. They always do, and that’s half the fun – even if the biggest stumbling block here is a telegraphed cheeriness that leads to obvious happy endings. You’re watching for Jake Johnson’s signature man-child snark, which he wheels-and-deals with every emotional blow. Enjoy Swanberg’s lesson about the art of losing, complete with a nice sunshiny finish that keeps second chances always within grasp. Whether it cheapens the tension or not.