Win It All

Gambling is consistently a dramatic go to because of its inherent dramatic stakes. Money is on the line and someone is going to win and someone is going to lose. That’s what makes director Joe Swanberg’s decision to examine gambling in “Win It All” so unique. Strictly indie, he is not a director typically associated with the usual sorts of pesky stakes everyone’s always prattling on about. Sure, his movies have big emotions, but those emotions typically arise from much more small scale narratives. And his often admirable refusal to indulge in obvious endings runs completely counter to the gambling movie’s favored denouement of one last Big Card Game. Yet “Win It All” does feature one last Big Card Game, marking the film as a curious experience, one where the stakes keep intruding themselves even if Swanberg nevertheless seems determined to cast off those stakes-y shackles.

“Win It All” is spurred forward by Eddie Garrett (Jake Johnson), a degenerate gambler who can’t afford a cup of coffee, being given a duffel bag by an ominous accomplice about to be squired to the slammer. Upon the accomplice’s return, Eddie is guaranteed $10,000. Ah, but what if the duffel bears more than $10,000? The bag, of course, is the narrative bomb and Eddie, frankly, held out longer zipping open that duffel than I would have bet. The bag contains, as it must, swaths of cash, of which Eddie takes a little, gambling it and winning, prompting him to a gamble a little more and lose, gamble a lot more to win back what he lost, lose all of that, etc. That seems tailor made for crazy schemes to get out of the red but “Win It All” mostly remains low key, approaching this crisis pragmatically rather than with all manner of comical complications.

The middle passages, in fact, center on the emergence of a support system for Eddie. Eddie’s brother Ron (Joe Lo Truglio) owns a small business and brings Eddie on as an employee, driving him firmly but lovingly, while Eddie also begins a relationship with Eva (Aislinn Derbez), a less than thought-out character, mostly existing to suggest something to which Eddie can root himself. And while Derbez and Johnson work charmingly enough together they, frankly, have less chemistry than Johnson does with Keegan-Michael Key playing Gene, a fellow gambling addict in recovery who Eddie calls his “sponsor”, a term to which Gene remains resistant in their scenes together where humorous give and take is laced with lots and lots of skittishness. Indeed, in his little time on screen, Key, with a semi-manic don’t-push-me temperament makes clear how precarious the straight life is.

Often the getting-it-together portions of movies like this are less than earnest, limited to a montage, a means of building up the character so he/she can come crashing back down. And while there is a montage, Swanberg goes beyond that, making Eddie’s rehabilitation, grudgingly doing the Day-by-Day, the true focal point. There is nothing much new here, yet it still mostly comes off and that can be attributed to Jake Johnson. He partially came up through improv, forming his own comedy troupe, and was also the inspiration for the web series Drunk History in which celebrities, uh, drunkenly recount history. I don’t mean to be flip. Johnson has an ability to make lackadaisical, off the cuff sounding monologues rather charismatic, an ability that matches this character, always begging, always assuaging, always assuring, sound incredibly genuine, trying to convince himself in the moment as much as he’s trying to convince whoever he’s speaking to.

Yet as “Win It All” becomes more concerned with Eddie’s bit-by-bit growth, the more it writes itself into a hole, needing to return to the duffel bag subplot, which theoretically should only add to the urgency but starts to feel more like a plot point that should have been jettisoned on a rewrite. Because as “Win It All” gradually proves itself a movie better without drummed up suspense, when the suspense gets dutifully drummed up, the trap the movie has set for itself is sprung and, sure enough, Eddie, metaphorically speaking, gets caught in a little left field melodrama. It might have been better if he just went up in a puff of smoke.