If nothing else, Joe Swanberg’s Win It All shows that nothing good ever happens in underground gambling dens or high-stakes poker games. Although the story’s low-key dramatic crux revolves around gambling, this isn’t exactly a movie about gambling. That’s a good thing, because ultimately gambling movies have as predictable an arc as most crime movies, and it usually involves a steely-eyed sharp just trying to make their get-away-free amount of money in one last high-stakes game.
Of course, that’s where Win It All ultimately dead-ends as well. Fortunately, it invests more time and effort along the way in things besides the next drop of the cards.
Instead of the expected action junkie, Eddie (Jake Johnson) is no great shakes at the cards. He works part-time as a parking attendant for Chicago Cubs games. Otherwise, he appears to hang out at a crummy bar that has good specials on Old Style. Every now and again, Eddie pops down to Chinatown to gamble whatever bit of money he’s managed to put away. It doesn’t seem to give him much joy. He lurches toward the table like he’s being pushed and afterward looks like the El just ran over his dog.
Why? Because, as his frustrated sponsor Gene (Keegan-Michael Key) says, in between berating him for blowing off basically every Gamblers Anonymous meeting, Eddie is simply a loser. There isn’t much evidence to disprove that theory. That’s why, when Eddie finds friendly but still-threatening acquaintance Mickey (Jose Antonio Garcia) sitting in his kitchen with a mysterious bag and offering a terrible proposition, it’s clear that Eddie will accept. It’s also clear that, instead of waiting for Mickey to get out of jail and pay him $10k just for watching the bag, Eddie will instead eventually riffle through it, take out some cash, and play some cards.
By refusing to give us much of the highs that come from cinematic poker — think of the flashbulb jitters of movies like Rounders (1998) or The Gambler (2014) — Swanberg and his co-writer Johnson turn the focus back opon the relationships that Eddie is potentially blowing up on his race to the bottom. On one of his very few winning streaks, a feeling-flush Eddie comes across bright-eyed and responsible Eva (Aislinn Derbez), a soon-to-be-girlfriend who’s so promising that he even brings her to meet his bothersome brother Ron (Joe Lo Truglio). Delivered in the unhurried, high-mumblecore mode of Swanberg and Johnson’s earlier Chicago collaboration Drinking Buddies (2013), the movie is ultimately more at home in the diners and bars of its determinedly ungentrified locales than at the poker table.
This isn’t to say that Win It All doesn’t serve up some tension amidst the relaxed and jazzy humor. Swanberg occasionally throws up on the screen a dollar amount as a handy reminder of how much up or down Eddie is. It’s a device that becomes more urgent as the stakes ramp up; Eddie’s ability to lose money he can’t replace from a potentially very dangerous man sharpens even as his relationships with Gene, Ron, and Eva start pointing to a kind of normalcy. The script mostly skimps on Eddie’s self-destruction, allowing a few pointed hints at his history of dark deeds to fill in the blanks.
It doesn’t seem quite enough, though. There’s charm aplenty here, whether in Johnson’s patented shambolic chaos-bear routine (tweaked only about 20 degrees from his character on 2011’s New Girl) or the unhurried appeal of the ensemble (keep an eye peeled for Arthur Agee, star of Steve James’s Hoop Dreams, 1994).
While Swanberg and Johnson’s script keeps a string of about-to-drop other shoes dangling over the narrative at all times, it still has the rickety feeling of something knocked out over a long weekend and a few beers. There’s nothing inherently wrong in that, of course. But once Win It All drifts lightly across the finish line, it’s hard not to wish there had been a little more at stake.