Movies focused on gambling seem to have a formula. A scrappy underdog wins a big pot and their life is changed forever. It doesn’t seem to even matter what game they’re playing. This is the biggest problem with Jake Johnson and Joe Swanberg’s “Win it All.” You’ll see the winning hand before it’s even dealt.
That’s not to say “Win It All” is lacking in charm. Johnson plays an affable loser with a compulsive gambling problem. During the day, he’s a parking lot attendant outside Wrigley, getting paid cash under the table. Every night, he blows that cash in backroom, speakeasy poker games. His call to adventure comes in the form of a mob debt collector facing a prison sentence. The collector has a bag he needs stored. A bag he’s willing to pay ten grand to keep watch over. Johnson quickly finds out the bag is packed with stacks of cash. As expected, this is a lot like leaving your stash of pure Colombian blow with a class A junkie.
Johnson has a decent set of comedic chops. The spectrum of his performance swings between angry exasperation and joyful relief. Johnson is also flanked by two veterans from the sketch comedy world, Keegan Michael Key and Joe Lo Truglio. I love seeing Key in just about anything, but I doubt he spent more than two days on set for this. Lo Truglio on the other hand landed the meaty role of Johnson’s comedically mundane brother. It’s the kind role he’s expertly played since starring on “The State.” Some of the funniest scenes revolve around Johnson and the lesser known supporting cast. Steve Berg, who absolutely kills on Idiotsitter, Arthur Agee, of Hoop Dreams fame, and newcomer Nicky Excitement do yeoman’s work as Johnson’s dimwitted pals. Aislinn Derbez does a fine job as the obligatory love interest. At times, her story felt shoehorned in, but she does her best with what she’s given.
The movie has a grittier look, both in film quality and setting. The digital cinematography gives it a little bit of a student film feel, but it matches the general aesthetic of the film. The Chicago locations all look a little rundown. It isn’t all highrises and shots of the Sears Tower (or whatever they’re calling it now.) We mostly see blue collar neighborhoods that could easily pass for anywhere someone might work in a factory. The most distinctly Chicago thing in the whole movie is seeing people happily throwing back Old Styles.
Overall, it’s a decent flick. A little formulaic, but that comes with the genre. Count this as another success for Swanberg. After directing episodes of “Love” and “Easy,” he’s put together a decent string of collaborations with Netflix. One reason the script Johnson helped penned works is that it forgoes the normal trope of cartoonish villains. It was nice to not see an inarticulate clone of Malkovich’s character from “Rounders.” Johnson’s greatest adversaries are his own stupidity and willingness to succumb to addiction. The emotional stakes are a little lower, but it still rakes in a nice pot in the end.