Movies about gamblers are fun. Movies about reformed gamblers, on the other hand, tend to put the viewer in the uncomfortable position of rooting for the protagonist to relapse. That’s the challenge taken up by Joe Swanberg and Jake Johnson—who previously collaborated on Drinking Buddies and Digging For Fire—in their latest joint effort, Win It All. Can they sustain viewer interest in a story about a literal loser who’s making a sincere, committed effort to overcome his gambling addiction and straighten out his life? Not really, as it turns out, but there’s enough disreputable behavior bookending the righteousness, and enough solid jokes along the way, to make the effort moderately entertaining.
Johnson doesn’t deviate much from his winningly hangdog New Girl persona as Eddie, who’s first seen getting cleaned out in a backroom poker game. (The film is set in Chicago, which is within driving distance of several legal riverboat casinos, but Eddie doesn’t frequent those, presumably for budgetary reasons.) Foresight and impulse control aren’t among Eddie’s virtues, so it’s unclear why a gangster friend (José Antonio García) who’s about to do several months in prison entrusts Eddie with a duffel bag, instructing him not to open it and promising him a whopping $10,000 payout if it’s kept safe. In no time at all, Eddie has opened the bag, found the bundles of cash within (underneath what looks alarmingly like evidence from an unsolved murder case), and convinced himself that this is his opportunity to finally make a big score. Montages of card games and racetrack excursions ensue, with onscreen graphics keeping tally of the results. After one terrific night, he’s up $2,148! But roughly 24 hours later, he’s down $21,243.
It’s at this point, fairly early in the movie, that Win It All does a bit of gambling itself, by having Eddie genuinely realize that he needs to change. After years of rejecting offers from his brother (Joe Lo Truglio) to take a job in the family landscaping business, he joins the crew and discovers, to his surprise, that he actually enjoys doing honest manual labor for a living. He also embarks on a romantic relationship with a single mom (Aislinn Derbez), growing attached to her daughter and becoming more invested still in the idea of standard-issue adulthood. All of which is admirable, obviously, but not exactly riveting to watch. The film’s middle hour leans hard on Johnson’s scruffy charm and occasional comedic interjections from Keegan-Michael Key (playing Eddie’s long-suffering Gamblers Anonymous sponsor) and Lo Truglio; the latter has a great bit in which he pretends to be furious with Eddie, then admits that he’s only kidding… but admits it in exactly the same angry voice that he’d employed in the prank. The bit feels much more like a State sketch than it does like Swanberg, but it helps keep Win It All from totally flatlining.
This is far and away the most conventional and accessible movie that Swanberg—a prolific, often idiosyncratic no-budget filmmaker—has helmed to date. Narrative expectations are cheerfully fulfilled: Having grown to appreciate his new, stable life, Eddie is forced to take part in a climactic high-stakes poker game, as his gangster pal is about to get sprung from prison early and thousands of dollars are still missing from the duffel bag. (The plot has a lot in common with Rounders, actually, minus Edward Norton’s enabling Worm character and the attention to realistic poker detail.) Even the sex scene is uncharacteristically chaste for Swanberg, fading to black before either party so much as removes a single article of clothing. It’s as if Swanberg, like Eddie, wants to demonstrate that he can play by the system’s boring old rules. They both make it look at once laudable and slightly enervating.