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To gambling, the cause of and solution to all of life’s problems

by Thom Yee


Win It All images courtesy of Netflix

Manifest destiny is one of those concepts that’s surprisingly easy to throw around, even if we don’t all have a firm grasp on 19th century colonialism, because it’s so tempting to believe what we’re doing is right. What we’re doing is inevitable. What we’re doing is something we ought to be doing, something that will bring about the way things should be and, perhaps, always should have been. It’s a lot like gambling that way. It’s an act of faith.

Gambling is something you do at least partially because you believe it can help you to meet your end goals. That doesn’t necessarily make it a lot better or an easy thing to condone, but I think it makes it easier to understand. You know there’s a chance you could win, so you can’t help but believe you will win, whether you’re a high-stakes poker player, a slot-machine jockey, or a part-time gambler, visiting betting sites to lay it all on the line for your favourite sports team, something we can finally do here in Edmonton now that our Oilers have made it to the playoffs for the first time in 11 years (#GOilers). In the case of sports betting, it’s something that can even make you appreciate the game that much more (#LetsGoOilers). In that way gambling’s a lot like life actually, a game of risk and reward. And, like life, you can’t win if you don’t play.

Or you can just watch a movie about it.

What’s it about?

Eddie Garrett (Jake Johnson) isn’t on what you would call the right track, scrounging for work, spending his nights drinking with buddies, and regularly gambling away whatever little he manages to save, so when Michael, a local criminal, offers Eddie $10,000 simply to hold on to a bag for six months he naturally agrees. When Eddie discovers the bag is full of cash, however, he quickly puts himself in the hole by gambling most of it away, something that forces him to finally put his life together to replace the cash he lost, but when Michael reveals he’ll be returning early, before Eddie’s earned the money back, Eddie must either find a way to stay on his current path or go back to gambling to ‘Win It All’ (Ooooh, I used the name of the movie!)

So… Win It All isn’t a movie that’s likely to jump out at you in any particular way, shape, or form, but I can give you two reasons why you should consider it:  It’s on Netflix and it stars Jake Johnson.  While the former has grown to become an institution in most of our lives, I can’t quite say the same of the latter, even if he keeps taking significant steps in that direction. Jake Johnson has quietly built a surprisingly robust career for himself, having featured primarily in indie fair (like Win It All) before starring on Fox’s New Girl and, lately, landing roles in some pretty major movies, including 2015’s Jurassic World and the forthcoming The Mummy alongside Tom Cruise.  He’s far from a movie star, he doesn’t look, act, or even move like one, but Jake’s getting himself some pretty plum roles, and for me, that’s a great thing to see because he’s just such a likable presence on screen (so likable in fact that I consciously chose to refer to him by his first rather than last name just now).

While first available to the public on Netflix, Win It All actually had its premiere at this year’s South by Southwest, a music, film, and interactive media festival with live acts, conferences, and trade shows that, despite its artistic appearance, is really mostly a word-of-mouth-oriented marketing vehicle where things like Twitter got their start. The latest work from director Joe Swanberg, Win It All is a movie that can, at least outwardly, be associated with the early 2000’s mumblecore movement of films known for their low budgets, low production values, and largely improvisational natures. As intriguing, creatively liberating, and ultimately terrible as that probably sounds (depending on your beliefs and tolerances), it diverges from those movies in one significant area: It actually has a clear narrative path.

Is it any good?

The first thing you’re probably going to notice about Win It All is that… it kind of looks like crap.  It’s grainy, its colour palette is stifling and muted, and it has that signature handheld shakiness that makes you feel like you’re there.  It’s suffocating really, and that feeling informs the themes of the movie while creating an atmosphere that makes the movie visually evocative of more classic cinema, like something out of the ‘70s. The settings look uninviting, the basements and backrooms of the kinds of businesses you usually try to avoid, not because they’re dangerous necessarily, but because… well, only losers would hang out there. It’s a dingy, dark world full of normal-looking people who mostly live on the wrong side of the tracks.win-it-all-poker-table

Something you may be less prone to immediately noticing is that Win It All is a comedy, and this is where the first real divide between whether or not you’ll like this movie shows up. Despite being quirky and not overly serious, and despite employing comedic actors like Jake Johnson, Joe Lo Truglio, and Keegan Michael-Key, there’s nothing laugh out loud about Win It All, and there’s actually a lot of quiet despair onscreen. The humor you’ll find in Win It All is subtle and understated and built on the humor naturally found in life, the kind of things you’ll smirk or grunt at rather than laugh, and you have to be in the right mood for its comedy to work.

The other thing that will have to sit right with you is how much you like Jake Johnson because this is a movie that’s utterly dependent on liking the lead and his performance. I like Jake Johnson, the affable, lovable loser role he’s usually saddled with pretty much always works for me because he knows how to play it just right, obviously a down-and-outer but never quite defeated, and he’s always funny in a way you can’t ever imagine taking him seriously. At one point he refers to one of his friends, holding the bag of money at one of his poker games, as his “bag man”, and it’s something that tickled me just right and caused me to laugh endlessly, but more on the inside and not at all on the outside. If Jake’s underdog charms haven’t worked on you in the above trailer or on shows like New Girl though, there’s almost nothing to see here.win-it-all-race-tracks

So should I see it?

When I think back about watching Win It All, I’m reminded of the advice I’d heard an accountant give to a famous clown once:

Gambling is the finest thing a person can do, if he’s good at it.

And then that clown took all of the money he’d made in his latest business venture and bet it against the Harlem Globetrotters (he thought the Generals were due).

Movies like Win It All run on almost no money, and because of that, there’s an authenticity to it that allows its themes to shine through, even if they’re themes that are harder to verbalize or more nuanced than single-sentence morals like “slow and steady wins the race” or “appearances can be deceiving”. At one point in the movie Eddie gets himself into a high-stakes poker game that his winning or losing of depends largely on your perspective, and so the themes aren’t as simple as just saying something bad about gambling or labelling it as an addiction or disease, instead they shift more towards a question about committing to the choices you’ve made. Because of this, the one absolutely positive thing I can say about Win It All is that it feels right, it understands how mediocre it can be to exist in a world without many good choices and how great it can be when you finally make the right one.

But to be honest, this level and type of authenticity and nuance frequently verges on boring, and Win It All never really has anything to say or do in the sense of dynamic storytelling or comedic pratfalls. If the sequence in the trailer (above) of Eddie saying “Oh no” to himself over and over as he discovers more and more money in the bag he’s holding doesn’t tickle your funny bone, then you’re not going to find much here. If you can see how something like that might work for you though, you’ll find yourself gradually but surely becoming more and more invested in the story and what ultimately happens to Eddie. You start to fear for him, you start to get a sense of heartache and longing for where he seems to be going and where you suspect he’ll end up.  That said, it’s also very easy to keep going with your life having never seen it. It’s like manifest destiny that way. Wait. I might not have been using that term right.

Thom’s Win It All final score


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