The following is a review of Win It All – Directed by Joe Swanberg
Mumblecore filmmaker Joe Swanberg’s newest film – Win It All – is a Netflix ‘original film.’ As you may remember, Win It All isn’t Joe Swanberg’s first Netflix release. In 2016, Netflix released the first season of Joe Swanberg’s anthology dramedy series Easy, which was a show that I enjoyed even if it didn’t blow me away. I’m much more fond of Win It All, which, I believe, gives us one of the strongest performances Jake Johnson, who I’ve become a big fan of, has ever given.
Jake Johnson plays Eddie, a gambling addict with absolutely no luck, who one day comes in possession of a lot of money. However, the money doesn’t belong to him. Eddie has agreed to take care of a duffel bag containing lots and lots of money for an acquaintance, who is going to prison for the next six-to-nine months, in exchange for $10,000.
This is all well and good, until Eddie has to scratch that itch again. Eddie takes $500 from the duffel bag and actually wins a good deal of money. This newfound luck leads him into the arms of a wonderful woman (played by Aislinn Derbez) who is, without a doubt, too good for a gambler that has no idea what to realistically do with his life.
However, when an elated Eddie casually starts gambling again his luck is nowhere to be found, and he soon starts taking more and more money from the prisoner’s duffel bag. Soon Eddie loses way more than he can possibly get back with his luck, and he is forced to return to his old gambler’s anonymous sponsor (played by Keegan-Michael Key) and his family for help.
I had a lot of fun with Win It All, but it’s a movie that I think it is easy to dislike or reject and brush over. Swanberg’s latest doesn’t feel very fresh, and it is regrettably fairly predictable. Also, although the film effectively and smartly shows us a simplistic dollar counter so that we can get caught up in the horror of Eddie losing money he, most likely, is unable to get back, Win It All doesn’t properly drive home the impending consequences.
But even if Win It All doesn’t completely work as a nail-biting gambling movie, it definitely does work as a casual but confident character study, which Jake Johnson is terrific in. Eddie is a hapless guy who is stuck between two worlds. His no-direction lifestyle, which is driven by his gambling addiction, and his relationship with his family – and now this new woman in his life who he is completely falling for.
Eddie has to learn what is truly important to him. Is it drinking all night with his buddies before going out and throwing away money with no endgame in sight? Or is it just settling down, laying roots, and setting a course for himself? Over the course of the film, he needs to mature and realize what ‘winning’ really feels like.
Swanberg’s film feels very real and human. The relationships, the characters, and the reactions, indeed, feel very lifelike. Win It All won’t win over every Netflix subscriber, but if you take a chance on this film, then you’ll see a strong and charming performance by an underrated actor in an enjoyable gambling dramedy, which doesn’t outstay its welcome.
8 out of 10
– Jeffrey Rex
I'm Jeffrey Rex 