Win It All (2017)

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Independent cinema rules modern filmmaking, let’s be perfectly honest. The very definition of independent cinema just won Best Picture, and we are living in a world where independent cinema is the trendiest and most sought-after movement. American indie films, more than anything else, have forged a special place in modern cinema, to the point where it verges on being mainstream. Joe Swanberg has been someone at the forefront of the highly popular mumblecore movement, and his film Drinking Buddies managed to get high-profile fans in the likes of Quentin Tarantino. He has worked steadily in the world of independent film, and reunites with his muse, Jake Johnson, for a film that serves as the best work for both men, and one of the better independent films this year (I say that like there are bad independent films this year, which there really isn’t so far).

Win It All is about Eddie (Johnson), a steadily unemployed man who has an addiction to gambling. When his friend goes to prison and leaves Eddie in charge of his belongings, Eddie is shocked and chagrined to find that has left around $20 000 in cash, and being the compulsive gambler that he is, Eddie loses all of it, and needs to find a way to earn that money again before his friend is released. The problem is that when his friend has his prison sentence shortened, Eddie needs to scramble to make a plan to gain all the money he lost previously, through any means necessary.

Jake Johnson is obviously a very talented actor, and I am pretty sure that his talents are being dreadfully wasted on New Girl, and from what I’ve seen, they really are. While it is a reliable show, it is certainly not the showcase for Johnson as some of his independent work has been. However, this isn’t to imply that Johnson is necessarily Marlon Brando or Peter O’Toole, and he isn’t always the strongest actor on his own merits. He is one of those actors that does well with a good script, and he is beyond capable of bringing a character to life, granted he has the support of great writing. There is something about Win It All that I find fascinating in this regard – he co-wrote the script, and managed to write himself (along with the very capable Swanberg) to his finest performance yet. It isn’t a vanity project – by all means, Eddie Garrett is not a particularly likable character, but Johnson is wonderful in it. He has the indie sensibilities that made stars of actors who had their roots in independent films. Johnson really is wonderful in Win It All, and it stands as his best work yet. Considering that his career is still relatively young, and he has many more years in him hopefully, this is the perfect performance to showcase his talents as a leading man, and with a bit of diversity he could rise to being one of the most extraordinary actors indie cinema could hope for.

Independent cinema also manages to often bring some interesting casts together, and while Win It All may not boast a particularly strong cast, it certainly does have some interesting actors in it. Joe Lo Truglio always steals the show on Brooklyn Nine-Nine, and playing Johnson’s older brother here, he is hilarious and does well with the character. Aislinn Derbez plays Johnson’s love interest, and while her performance started out very shakily, she showed considerable charm throughout, and while she doesn’t have a well-developed arc, she is still great in the film and Win It All is a great introduction to a very promising young actress.

Keegan-Michael Key is always a welcome presence in any form of media (honestly, I would watch informercials with him in them, but then again, who wouldn’t?). I have to say that Key’s career is going in a very different direction than that of his comedy partner Jordan Peele, who has proven himself a talented director with this year’s best film, Get Out. Key is really making a name for himself as a reliable supporting actor in indie films – he just needs that one leading role to propel him to the status of a great actor, because what made Key & Peele such a successful show was not only the fact that the titular duo were wonderful comedians, they were also incredible actors, and now that the show is done, here’s hoping for more opportunities for Key, who is someone who has shown considerable promise as an actor before, he just needs a leading role to cement that fact. I actually can’t believe that I dedicated a whole paragraph to Key, who has around four or five scenes in this entire film. I think the message is clear – Keegan-Michael Key is talented and deserves a cinematic breakthrough.

Win It All is a gambling movie, a sub-genre I don’t really have much patience for, because they can often be very boring. One recent example is Mississippi Grind, which despite having a fantastic performance from Ben Mendelsohn, was a bit dull. Gambling movies are often just forgettable excursions into the world of excess and faux-complexities. Win It All finds the biggest problem with gambling movies and eliminates it right out the gate – convolution. Win It All has a simple storyline and it follows a logical order, and rather than being an experiment in showing the high-stakes lives of gamblers, it manages to just follow a single coherent plot point, without too much excess, to create a rivetting and interesting entry into a very problematic genre. I appreciate the rapidity and simplicity of this film, and it proved that a film about gambling addiction can actually be logical and not confusing to those of us who don’t really enjoy gambling all that much, and rather than being a film about gambling, it is a film about gambling addiction, and treats the subject like Days of Wine and Roses treated alcoholism and Requiem for a Dream treated drug addiction.

I won’t begrudge independent films for becoming very trendy – there are no people in the film industry that deserve fame, acclaim and popularity quite like independent filmmakers. Joe Swanberg has created a film with mainstream appeal without distancing the film too far from its roots in micro-budget independent cinema. I am not sure what trajectory Win It All will provide for Swanberg’s career, but the positive buzz and natural excellence of the film makes me suspect he is in for quite a breakthrough here. I just hope when he has his breakthrough, he keeps the same humble nature of filmmaking that he shows here, because it would be a great loss for him to lose his singular vision. But both he and Johnson deserve bigger breakthroughs, and god-willing, they will happen soon.

Please watch Win It All – it is a delightful film that takes serious subject matter and presents it to us in a way that is funny but also very serious. Jake Johnson gives his best performance yet, and Joe Swanberg cements himself as a truly talented visionary in independent films. I have to thank Netflix for giving many filmmakers a platform for having their work seen in unique ways, and the combination of great cinematic content with the popularity of Netflix will hopefully lead to more diverse and fascinating distribution of films, allowing the visions of independent filmmakers to be seen by more people. Win It All is a great film, and I think it should be given credit and acclaim for being so good, and I hope everyone will give this film a chance, because it really is great.

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