'Win It All' just should've been about the Cubs

At a glance, you might suspect Jake Johnson and director Joe Swanberg of overcompensating the Chicago-ness of “Win It All,” their third movie together and first since the thoughtful, uncharacteristically L.A.-based “Digging for Fire” – which followed “Drinking Buddies,” a terrific movie focused on employees at Avondale's Revolution Brewing. 

In “Win It All,” the Evanston-native star, boasting the same facial hair and blue-collar, beer-driven dudeness of “Drinking Buddies,” plays Eddie, who works as a Cubs parking attendant. In a scene at one of the city’s completely ordinary bars, a guy wagers $20 and an Italian beef on a game of pool. And Eddie takes the Red Line from Addison to a hidden-away gambling spot in Chinatown, where his best skill is losing. 
 
So there’s plenty of homegrown credibility to the latest from the Chicago-based Swanberg (whose most recent outing, the Chicago-made Netflix series “Easy,” was occasionally pretty good and overall just OK). But this is the first time these two have collaborated and seemingly didn’t know what they wanted to achieve.

No longer concerned with issues of romantic commitment, Johnson and Swanberg (who, as with “Digging for Fire,” tackled the script together) struggle to find new ways to approach other kinds of growth and loyalty. Eddie’s brother Ron (Joe Lo Truglio) tells him, “At a certain point you have to grow up,” which at a certain point every movie should just avoid. As you probably can expect, Eddie’s late father had a gambling problem as well, though that leads to no more consequence than his unconvincing relationship with Eva (Aislinn Derbez), a nurse with a 7-year-old daughter. While Eddie tells his brother that he likes feeling like a functioning, productive member of society after he starts working for Ron in the family landscaping business, and there’s the clear sense that having someone to improve for makes him better, the movie never confronts his feelings about if he’d be ready to help care for a child.

In fact, much of “Win It All” feels under-conceived and at arm’s length, as if setting up a situation reminiscent of yet another remake of “The Gambler” and letting it play out in Swanberg’s likably casual style will provide enough character to compensate for the lack of tension. (Eddie’s tasked with guarding a bag while its owner spends time in prison, and you can probably guess what’s in the bag and how responsibly its handler deals with those contents when given the opportunity to bet them.) But the threat feels too minimal, regardless of the addict’s revolving door of euphoria and failure. Eddie’s level of skill and addiction feels unclear, and his compulsive behavior results in little in terms of his relationships with friends or family. His fear of the bag’s owner isn’t developed beyond “This guy is getting out of prison and will be mad.”

Johnson succeeds in Eddie’s uncomfortable attempt to balance efforts toward normalcy with the bubbling, hidden panic inside, and Keegan-Michael Key, who has had a supporting performance in approximately 42 percent of movies in the past few years, has a couple good moments as Eddie’s sponsor. Yet “Win It All,” which isn’t funny and eventually hinges on a pretty cheap ending, is too non-committal to stick. Anna Kendrick’s behind-the-curve aunt in “Happy Christmas” went through more, less obvious growth; here, Johnson’s unreliable uncle experiences only the familiar, right up to the big game that will either help him win it all back or push him farther down the hole.

If only they could have adjusted the shooting schedule a little; with that title and that initial job, there was another “Fever Pitch” unfolding right in front of them, perfect for a perennial loser finally winding up on top.

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