Win it All (2017)

Starring: Jake Johnson, Joe Lo Truglio, Keegan-Michael Key, and Aislinn Derbez
Grade: A

I know this is random, but the white suit Jake Johnson wears to the racetrack combined with the sunglasses is such a cold look.

Summary

In Chicago, Illinois, Eddie Garrett (Johnson) parks some cars for some quick cash around Wrigley Field. After making that cash, he goes straight to some back-alley poker place he frequents to make some big money, but he doesn’t do too hot. Being there all night, he leaves in the early morning, heads over to the local convenience store to get a quick bite and promises the owner he’ll pay him back at the end of the week. We can see this is something he does a lot. With what we see in the opening and how he’s known by the locals, we know Eddie has a very clear gambling addiction. He gets to his house to find known gangster Michael (Jose A. Garcia) at his kitchen table waiting for him. Michael offers him a business proposition. Since he has to do some prison time coming up (6 to 9 months give or take), he wants Eddie to store his duffel bag in his house, so the cops won’t confiscate it. If he holds it until he gets out, Michael gets $10,000 cash. Eddie wonders what’s in it, but Michael is adamant that Eddie doesn’t need to worry about any of that. Just leave it alone, store it, and forget about it. If he does this very simple task, he’ll get his money. It seems simple enough, so Eddie agrees to it.

Later on that day, Eddie’s older brother Ron (Truglio) calls and leaves a message for him, asking him to come over to his family’s house since they haven’t seen him in a few weeks. As Eddie bonds with his nephew and Ron, Ron’s wife Kris (Kris Swanberg) drills Eddie with questions and subtly disses him for still parking cars, bringing up how he talked about opening a bar. Eddie insists plans are still on for this but him and his friend Arthur are still “discussing” details, which we know isn’t true. He changes the subject about how he’s opened up his own “storage business”, though she doesn’t know he’s referring to the duffel bag deal he agreed to earlier in the day. After being questioned on the specifics, Eddie gets a bit agitated, so Ron has Eddie come outside with him to help with the trash. Sharing a joint, Ron once again offers Eddie to come work for him in his landscaping business that he took over from their father because it’s much more stable and secure. Unfortunately, Eddie has no interest in being a landscaper. Once he goes home, he considers opening the duffel bag but decides against it, going to the bar with his friends. It doesn’t take much thinking however, for him to go right back home that night to open it anyway, regretting it as he does it.

Inside, he finds a rope, a sledgehammer, and a lot of cash.

The next day, Eddie meets with his annoyed friend Gene (Key), his recovery sponsor, though Gene doesn’t claim this because Eddie hasn’t been to a meeting in six months and chastises him for it because he knows Eddie’s not progressing. He tells Gene of his plan of taking only $500 from the bag to gamble with it because it may put him into position to win some big money. If he does, he can put the original $500 back in the bag and everything will be square. Gene counters with Eddie’s losing streak and how he knows if Eddie takes $500, he will take more. Even though he insists he loses because he never had the bankroll, Gene knows he will fuck this up. Lying to his face, Eddie “agrees” with Gene.

Immediately after, he grabs the money and goes straight to the gambling house he frequents.

That night, he leaves with $2,148 and goes straight to the bar with his friends to celebrate, buying drinks all night for them. On the way to the bathroom, he accidentally gets in the way of Eva (Derbez). Once he hits the bathroom, he starts to think about her and runs into her again on the way out. This time she notices him, and they start sharing glances at each other when they go back to their tables with their friends. He pays his bartender friend to deliver drinks at her table and uses the moment to come over and talk to Eva. With Eddie’s promise of buying all their drinks to ease the tension, they combine friend groups for the night, and everyone has fun, with Eddie and Eva really hitting it off. To end the night, they separate from the group, get some food, and talk. He walks her home and secures the phone number. Unfortunately for him, they can only do a breakfast meet up because she’s a nurse and is always busy. He knows he’s not a morning person but agrees to it because he doesn’t really have a choice.

His new standing total after the night is $1,975. Still riding the high from the previous day, he goes to the racetrack to gamble some more but loses a lot, forcing him to call his friend Nick to bring the duffel bag to him. Unfortunately, the track gets rained out after his cold streak, so everything is postponed. He goes straight to the gambling house and loses more. He starts to freak out, but when he goes back to the car, he gets even more money from the bag and goes back in. Bad hand after bad hand, he loses even more. He’s now in the negatives.

-$21,243 to be exact.

After he flips out in the alley, he gets a text from Eva to meet up with her for breakfast, so he does. She talks about how her mother lives with her and how she has a seven-year-old daughter. Fortunately for him, the father is not in the picture. The breakfast goes very well and once he walks her back to work, he actually comes to the realization that he needs to change. He also needs help because of the amount of money he lost from Michael’s bag. After going to Gene for help and regrettably asking Ron for a job at the landscaping business, Eddie tries to get himself on the right track if things are going to progress with Eva. The problem is that he has a very small amount of time before he has to make that money back.

My Thoughts:

Using a limited budget to perfect, the fan favorite team of Joe Swanberg and Jake Johnson make Win it All one of Netflix’s most winning original comedies in recent memory. It’s breezy, fun, incredibly engaging, and effortlessly watchable, much like star Jake Johnson himself.

Personally, I could watch Johnson in pretty much anything. It can be in the simplest setting, premise, or whatever else. Something about him is so cool and natural to the point that he can light up the most general of scenes with his mere presence. He possesses a quality about him that works in a star role, romantic lead, best friend, or supporting character you wish you were friends with. Not all actors have this quality. Some are pigeonholed and can’t get out. Johnson has “it” though, and it’s obvious in everything he does, including in Win it All. Here, he plays a likable gambling addict that refuses to get better in Eddie. There’s a chance of striking it big every day, and he lives with this mentality, the addiction mentality. He has no future plans or motivations in life, totally fine with scraping by to live for the next day instead of building a future with a stable job and financial security. It puts him in shady places and gets him to meet some sketchy people. Nothing changes in his mindset though because he’s chasing the high of winning money no matter how much he loses because there’s always that small chance, he wins big. Then again, even if he did win big, he’d keep going until he lost the money, or he’d blow it all on a different day because hey, maybe he could win again. It’s hard for a gambler to admit his faults because when you win, you win a lot. However, when you lose, you tend to lose big enough to where you could lose everything. Eddie gets down bad, and it’s enough for him to finally admit to Gene, a friend who’s been hearing this stuff from Eddie for years, that he needs help.

Once this is admitted, we know it’s serious because even Gene takes a step back.

Some people need help changing. It can’t always work with one person saying, “You need help”. It’s not loud enough for some to hear. A true addict knows this is rarely enough to make a change. Sometimes, the addict needs to be faced with a real danger, a real problematic situation (a “hole” some would say) to force the person to change. This is what happens to Eddie. He puts himself in this situation by taking money out of the criminal’s bag and gambling with it on the off chance he makes a lot. Sadly, in true gambler fashion, once he wins, he continues until he loses all of it. Why did he do it? If he kept the bag in the closet untouched, he would’ve gotten 10k no questions asked. It could’ve been that simple. It’s hard though, isn’t it? Even as a viewer, I wanted to know what was inside. Curiosity is human nature. When Eddie takes a peek inside the bag, we can’t blame him. It would be hard not to do the same.

I love hearing him tell himself aloud “Don’t do it”, as we hear a drum beat to make the tension of the scene rise. It signaled exactly the amount of danger Eddie was about to get into, and he knows it. He’s telling himself not to before he does it like it’s going to stop him or something. He knows this will only spell bad news, but he can’t not look. When he sees the money, we both get that “Oh shit” moment because we both know he won’t be able to get it out of his mind until he gambles it. Why not? It’s right there! The chances of winning are massive now because he has a bankroll to back him! According to him, this was his only problem before. This is the thought process and because of it, we start to see behind the mind of an addict. The wheels start to turn. Despite him being in full control and getting advice from his friend and sponsor, he goes through with his risk-filled plan. He goes through with it for the small possibility, and he pulls it off! However, showing the addiction level Eddie is at, he starts feeling really lucky and spends about a day or two before he blows it by gambling more. The hole only gets deeper before he realizes he needs an out and seeing his desperation in key moments really gives us an attachment to the character, especially with Ron as he yells about how embarrassing his situation is.

It’s powerful stuff.

This may be a comedy about gambling, but addiction is the center of it, and it’s displayed in an entertaining and engrossing fashion. Win it All is really good, and Johnson’s performance is understated genius.

It’s not all about danger though. Love is a big part of it. Most of what we do revolves around it. Along with his back being against the wall because of the money loss, the potential of having more with Eva is enough for Eddie to want to work. He’s ashamed of his gambling life and never brings it up to her, even though we know that everything he does up until things progress with her is centered around it. He really likes this girl and he’s willing to work in landscaping, a job he never wanted, to help start his rebirth as the new Eddie. You can see how his eyes light up when he’s with her and talking about the future with his job. It’s backbreaking work, but it’s satisfying to earn your living. It’s part of recovery. He can finally feel it, and everything starts going well because he believes in what he’s doing for the first time in his life. He’s doing the right thing, and it’s because of Eva. Aislinn Derbez is wonderfully charming in her role and has an easygoingness to her that really matches Johnson’s energy. Their scenes together whether it be in an underground Mexican dance club or eating at a diner, felt so natural, you feel the love growing between them. We want this couple to win, which makes us really want Eddie to figure out his life badly.

Eddie was right. Him meeting Eva was fate.

When it comes crashing down because of the phone call from Michael, my jaw fucking dropped like Eddie’s. I should’ve saw it coming because everything was going too well. Even then, it turned the movie into something else, and I started panicking. It was frustratingly good because we know how well Eddie is progressing but when the situation changes, he starts looking for an out by asking Ron and Gene, but they think he’s giving up on the grind when that’s not the case. He’s just severely fucked and doesn’t know what else to do. God, it was great. The third act was an awesome pay off. The first two acts drew me in and made me fall for our admirable protagonist trying to finally change his ways, but the added conflict shooting a hole into everything he’s doing was a phenomenal choice in making this movie what it was. It shows what the human being can and will do when his back is against the wall, and it’s riveting to watch unfold. All he needed was that voicemail after almost giving up, and he hits us with the perfectly delivered line: “Let’s play cards man”. I loved it. Kudos to the divine intervention bit that halted what could’ve been a disaster by giving us a different disaster. With the drum beating and the frantic Eddie considering risking more, I was completely and utterly captivated by the action. I don’t want to ruin it, but it was so well done and such a great way to end a story like this.

The title is what it’s all about. Can Eddie win it all? We don’t know. Not even he knows, but it’s the possibility that drives him. This is what he’s chasing. Can he have his cake and eat it too? Can he get the money recovered and the girl, or does he have to give up his potential life with her because he’s running out of time? Watching him try to pull it off is exhilarating.

Jake Johnson and Joe Swanberg are the key here. Usually when they team up, there is some real magic, and it continues with Win it All. It’s everything combined with a grainy, raw footage look, to the excellent use of thunderous drums to build tension in so many scenes, to the showing of where his money is at on the bottom of the screen throughout his misadventures, and so many other small details that make this Netflix original film feel special. The acting carries it too. You can tell when Eddie talks to Gene about how he legitimately doesn’t want to be a part of the gambling world anymore how simple the script is line-wise and how it’s just Johnson owning the role and elevating the material. He makes what could be something simple into something special. Win it All is sneakily good and flew under the radar for most, but I assure you this one is a great watch.