Hot Take: Character driven Netflix Original that somehow forgets there’s a plot that needs attention until it’s too late. It’s still pretty good, though.
Most films about gambling get it wrong. Outside of Let It Ride and Rounders (I haven’t seen Mississippi Grind yet so that one is excluded from the conversation), the rest typically have some fatal flaw that causes it to lose credibility. Hell, even Rounders has a villain with the most obvious and ridiculous tell a poker player would ever have. Win It All avoids those fatal flaws by focusing on the main character, small time gambler Eddie Garrett (Jake Johnson) and his struggle with gambling addiction rather than the gambling action.
Eddie can’t seem to shake the gambling habit. The typical losing gambler who thinks the occasional big wins will last forever has tried Gambler’s Anonymous but failed to keep up the regimen and is mostly out of work (except for when he works parking cars for Cubs games). Despite his brother’s (Joe Lo Truglio) pleas to come work with him in the family business, Eddie resists the life that appears mundane to him and instead spends most nights gambling. A “business” proposition comes along that Eddie can’t resist. A less than reputable acquaintance named Michael (José Antonio Garcia) appears in Eddie’s apartment with a duffel bag and asks Eddie to keep the duffel bag safe while he serves a 6-9 month prison sentence with no questions asked about what is in the bag. If Eddie can pull it off, Michael will pay him $10,000. Eddie agrees.
Eddie’s curiosity about what’s in the bag gets to him over the course of a few movie minutes (Not sure about the real time) and once he opens the bags, he discovers the worst thing he could possibly discover: $100,000! Eddie borrows from the stash to seed what he believes will be an incredible run and it even starts out well. His first trip is a winning one and he celebrates with friends by buying drinks for the night and meets Eva (Aislinn Derbez), a single mom and nurse, and the two hit it off. Quickly and spectacularly (Shown through some basic graphic updates of his bankroll in the bottom right corner of the screen), Eddie’s winning ways don’t last and he turns to his sponsor Gene (Keegan Michael-Key) for advice and his brother for a job as he has to replace the portion of the cash he lost.
The premise is simple yet the characters are so genuine, it’s hard to get caught up in the details of the plot. Eventually, it predictably escalates as Michael’s release is accelerated to 6 weeks instead of the original timeline and Eddie’s plan to get the money back unravels. The third act is solid but let’s not spoil it with too many details. (This is “Spoiler Free” after all.) The character development is what holds the film together and Johnson and director Joe Swanberg (Also the film’s co-writers) show why they continue to work with each other.
While I wasn’t thrilled with the ending, it’s hard to argue with the film’s conclusion. However, there was something about it that felt like the filmmakers ran out of steam and decided to end it. Maybe it was on purpose but this feels like an attempt to prove the filmmakers are capable of conventional which hurts the overall product. Not enough to make it a bad film but enough to keep it from being a great one.
“Spoiler Free” Pros
- Jake Johnson
Johnson as Eddie is funny, charming and frustrating. The frustrating part is character driven and spot on if you’ve ever dealt with a gambler who always sees the world as half full even when his pockets are half empty.
- The Actions of an Addict
The monetary swings can be rough for a non-gambler but it is what keeps the blood of an addict pumping. The film portrays this in a most accurate light and gives some real credence to the story with subtle details and familiar depictions.
- It’s Not About the Gambling
What Win It All probably does best is never really make it about the drama of the gambling. While it portrays some familiar gambling tropes, it never dwells on the gambling itself which establishes that it isn’t really ever about the gambling. It’s a nice change from the films that focus on romanticizing gambling especially when poker is involved.
“Spoiler Free” Cons
- A Requiem for Convention
Maybe it’s a misread but it feels like Johnson and Samberg are out to prove they can do conventional.
- The Faux Indie Vibe
In addition to a conventional turn, the film feels like it is trying to give off an Independent vibe without appearing to be Independent. As deceptive as those dealing with gambling addiction can be, there’s a sense the filmmakers are being deceptive, too.