Film Review: "Win It All" (2017).

From the director of Drinking Buddies comes Win It All. This comedy film directed and edited by Joe Swanberg, and co-written by Swanberg and Jake Johnson. After losing $50,000 that wasn't his, gambling addict Eddie starts to rebuild his life. But an unwelcome surprise pushes him toward his old ways.


The film stars Johnson, Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key. The cast's strong performances drive thoughtful and mature comedy. Though the film has an absolutely loaded cast full of recognizable names, but does nothing much with them. Nonetheless, the large, talented cast is clearly thriving in the freewheeling style. Familiar faces are only a small part of the pleasures found in this odd picture, which enjoys the art of exploration, achieving genuine dramatic surprises in a fresh, inviting manner.

Win It All finds Swanberg working from a familiar palette, but in ways that suggest he's taking new and exciting strides as a filmmaker. Simple but affecting, deep without becoming preachy, and dancing on the line between comedy and drama. What makes the film such an enjoyable yet fleeting experience is how Swanberg lets these ideas flow organically into the film through his terrific cast and tight editing. The film is the tight, often funny and loosely scripted film that relies on the choices of the actors living in the moment. The film is not revolutionary, or even revelatory, but it captures some things that are hard to express, and it did so with a terrific cast. May not say anything revelatory, but the realization it imparts is no less valuable for it. The size of that ensemble and Swanberg's particular way of sorta hazily drifting from one half-overheard conversation to the next gives the picture a Robert Altman vibe that's never really been present in his work before. Conversations drift and weave, as do the people having them. Narcissistic melancholy dukes it out with beer-and-pot-stoked merriment. There is longing. There is foolhardiness. While you're watching it, the film may feel slight or tentative, but its cumulative impact is entrancing. Few films about a marital rift make so much of what seems so little. While it has its charms, Swanberg is tilling soil here that has been churned since humanity began, and he doesn't come up with very much that's new. What the film really has going for it is a solidly Swanbergian, unpretentious story. The scenes seem observed, not overwrought, and when you sense them adding up, it's not to some archly climactic epiphany. In classic Swanberg form, it makes an art out of extracting significance from small, fleeting moments. The film feels a bit more rushed than Joe Swanberg's previous efforts, but it's still a wholly entertaining dissection of one of life's many crossroads. The story may be slight, but the emotional impact of this mostly improvised drama is much deeper. The film wants to talk about serious topics and it wants to do so in a humorous light-hearted way. It succeeds. The film has an appealing honesty and an enjoyably low-key comic style.

Simon says Win It All receives:

Also, see my review for Drinking Buddies.