Movie Review: ‘Win It All’

Directed by: Joe Swanberg

Starring: Jake Johnson, Keegan Michael Key, and Aislinn Derbez

Plot: A gambling addict gets in over his head when a friend asks him to watch a bag of money.


It seems like every time I review a mumblecore movie, I talk about how mature they are getting. And, by that, I mean how much more deliberate and structured they are getting. They are starting to look like actual films. There was definitely some charm in their naturalistic, mostly improvised dialog, but what is even more impressive is how they retain that feeling without taking Seinfled’s show-about-nothing philosophy to the next step.

Part of it, I think, is that the movement may have found its perfect protagonist in Jake Johnson. This is his third outing with director Joe Swanerg, and this time around he earned himself a writing credit. When not working with Swanberg, Johnson is most likely to be seen elevating the material of an already competent network sitcom, “New Girl.” His self-deprecating and reactionary comedic timing is near-perfect, and he imbues the sad sack archetype with enough endearing empathy to make it more than just a schtick. He’s already nailing a candid style of dialog in a heavily scripted show, but when applied here, he polishes an already crafty subgenre.

Johnson plays Eddie Garrett, a small time gambler who hasn’t quite hit rock bottom yet but is circling it. He can’t lose much because he doesn’t have much, but that all changes when an acquaintance with much dirtier hands pays him a visit. He’s about to go to prison, and he drops off a bag of money for Eddie to watch. Why he thinks Eddie would be the best guy to watch it makes no sense, but it is the perfect McGuffin to put Eddie on his downward spiral.

This is where Swanberg and Johnson take in a different direction. Rather than build up to the moment when Eddie would hit rock bottom and repent in the final act, Eddie busts pretty early on and spends the bulk of the movie trying to better himself. It ends up being more like the sequel to the movie that I thought it was going to be. On a superficial level, it robs the movie of immediate stakes, however, in the end, you realize that it has giving Eddie things worth fighting for. Thing to be “at stake.” A job. A renewed relationship with his brother (played by the awesome Joe Lo Truglio). A new relationship with a pretty and charming woman (Aislinn Derbez, who gets damn close to stealing the show).

It is a little lightweight, but it is in good company, like the Sam Rockwell starring The Way Way Back or Jon Favreau’s Chef, only with that added naturalism of the mumblecore movement. In a post-modern marketplace, in the age of anti-heroes, where every protagonist must transgress so they can be punished, it’s refreshing to not be disappointed by a character you are rooting for.

Rating: 7/10