The most radical thing about “Win It All,” a perfectly agreeable little movie about one man’s attempt to put his gambling problems behind him, is that it follows a pretty conventional arc. More than a decade after director Joe Swanberg started cranking out rambling, improvisatory lo-fi movies, he has wound up funneling those tendencies into formula. At the same time, “Win It All” shows only just enough interest in narrative to keep its light entertainment value in play, while resisting the impulse to tell all but the simplest of stories. It’s still a talky character study, but Swanberg has steadily shown a far greater regard to holding the interest of a general audience, and this is the closest he has come so far.
It’s a reasonable outcome for a movie produced exclusively for Netflix, where Swanberg recently did a full season of his observational comedy “Easy,” further honing the challenge of funneling his ragtag style into more accessible material. Ever since 2013’s Olivia Wilde vehicle “Drinking Buddies,” Swanberg’s pace has slowed and he has experimented with handing his meandering approach to more experienced actors, from Melanie Lynsky (the centerpiece of “Happy Christmas”) to the ensemble of “Digging For Fire,” which included Sam Rockwell and Orlando Bloom.
All three of those projects also featured Jake Johnson, whose cheeky grin and leering expressions make him a natural fit for Swanberg’s usual fixation on bumbling characters suffering from arrested development. Swanberg and Johnson reteam for “Win It All,” and it’s a sturdy combination that feels more purposeful than anything else in the filmmaker’s oeuvre to date. The pair co-wrote this playful romp, which chronicles the plight of Eddie Garrett (Johnson), a small-time Chicago gambler seemingly incapable of getting life together. Eddie’s problems get complicated with one of the more familiar MacGuffins in film history — a duffle bag full of cash — and his slapdash attempt to make back its contents after he loses everything at the poker table.
Laced with a lively blues soundtrack and bolstered by Johnson’s rambunctious performance, “Win It All” lies somewhere between Hal Hartley’s seminal gambling caper “Looking to Get Out” and the everyman redemption stories of Frank Capra, though it’s a simpler and unambitious variation on those precedents. The concise plot finds Eddie constantly feeling the heat from his judgement older brother (an uncharacteristically straight-faced Joe Lo Truglio), who leads a comfortable family life and beckons his sibling to join his landscaping business. Instead, Eddie keeps going back to the tables, until he winds up so broke he has no other option but give in.
Half an hour into “Win It All,” and it seems as if Eddie’s already settled down, even nabbing a promising romantic interest in the genial Mexican woman (Aislinn Derbez, who also surfaced on “Easy”) he meets at bar. Plot tossed aside, Swanberg settles back into a series of rambling exchanges, and for a while it seems as though “Win It All” will simply examine Eddie’s experiences growing up. But his ultimately compelled back to his addiction, and faces dire consequences when he realizes the owner of the duffle bag will get out of jail soon, setting the stage for a frantic Texas Hold ‘Em climax that ranks as the first genuine moment of comic suspense in Swanberg’s oeuvre.
Swanberg and Johnson comically emphasize the slow pileup of problems for Eddie with monetary figures onscreen counting down the money he keeps losing, but ultimately that device serves a nice closing punchline about just how much Eddie has lost track of what he owes. Eddie shares some DNA with Anne Kendrick’s peripatetic troublemaker in “Happy Christmas,” as both are equally well-intentioned and disaster-prone. Swanberg’s loose style is a natural fit for a crisp story about leading a disorganized existence, and the new movie exists within the confines of Eddie’s shifting perspective. “Sometime’s the world is just perfect,” he says. “Sometimes it’s not.” For the duration of “Win It All,” the story shifts pivots back and forth between those two basic outlooks.
There’s much to enjoy about “Win It All,” but not quite enough to push it beyond the basic appeal of the material established early on. As if afraid to go too far with a conventional payoff, Swanberg keeps backing away from major conflict, instead settling for more cheery, aimless dialogue that owes a lot to its energetic performers. As with much of Swanberg’s career, that’s sufficient fuel to keep the movie rolling along and just enough to limit its staying power. However, by making a satisfactory crowdpleaser that doesn’t overextend itself, Swanberg has delivered his most traditional movie to date — and for this prolific filmmaker, who spent ages defying conventions, that’s nothing short of a radical step forward.
“Win It All” premiered at the 2017 SXSW Film Festival. It premieres worldwide on Netflix on April 7, 2017.