"My name is Eddie and I am a loser. I am addicted to losing."
Comedian Jake Johnson and lo-fi indie auteur Joe Swanberg continue their fruitful filmmaking collaboration, after Drinking Buddies and Digging for Fire, in the Chicago gambling comedy Win It All. It's another uncomplicated yet endearing film, co-written and produced by the pair, about rather conventional people and the ordinary but interesting circumstances surrounding addiction and anxiety over self-change.
Once again, Swanberg is able to assemble a likeable cast of mostly comic actors taking slightly more dramatic turns with Keegan-Michael Key and Joe Lo Truglio anchoring Johnson's charismatic starring performance as his reluctant Gamblers Anonymous sponsor and earnest older brother. The trio are aided by some nice minor roles to give the film an authentic working class sheen while making scenes of drinking, gambling, and hanging out all the more watchable while maintaining Swanberg's trademark loose, improvisational style.
Aislinn Derbez offers a charming if light performance as Johnson's working single mother girlfriend. In lesser hands, her character would likely be nothing more than a motivational factor for Johnson to reform his ways leading to a predictable change of heart. While seeming to have fairly standard story and predictable beats of the troubled gambler, Win It All avoids the pitfalls of the unlucky loser archetype especially concerning any comic romantic misunderstandings.
As usual, Swanberg is less interested in typical plot or dramatic tension than exploring the humanity of situations. Johnson as a gambler is easily identifiable and gets himself into likely trouble as an impetus for change that's still surprisingly compelling. Win It All only ever marginally echoes tropes from gambling flicks like Rounders while merging it with his penchant for exploring small but endearing character moments à la Drinking Buddies.
As the title suggests, Johnson's Eddie faces an inevitable big bet situation as a result of desperation in seeking a winning resolution to end his perpetual losing streak. After recognizing his flaws, faults, and going through a tough but rewarding redemption journey, this final detour into facing his gambling addiction head on could have come off as more troubling or menacing. But the way Swanberg and Johnson resolve his losing ways is a genuinely satisfying outcome.
Filmed on stylish 16mm stock, this is likely Swanberg's most accessible film. He clearly deviates from not only his early "mumblecore" roots but also his more recent string of naturalistic ensemble comedies featuring name actors to craft a cinematically intriguing, singular character piece. This filmmaking collaboration alongside Johnson as his main subject and muse has unlocked a meaningful well of interesting stories on screen.
Win It All is available for streaming now on Netflix.
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