Win it All

You don’t need to have an encyclopedia of cinematic knowledge stored in your brain-space to suss out which filmmakers have impacted the output of Joe Swanberg, but it helps. Also helpful: Google. Just track down an interview with the Chicago-centric filmmaker and presto, you’ll see him spill the beans on the page, frequently citing Elaine Mays and Paul Mazursky as his two top inspirations. Watching his films doesn’t hurt, either, especially 2013’s Drinking Buddies, which ends with a special thanks to Mays, and 2015’s Digging for Fire, which Swanberg dedicated to Mazursky, who passed away the year before its release. Say whatever you like about Swanberg as a director, but give the guy credit for wearing his influences on his sleeve.

Take Win it All, his latest joint, a Netflix-backed flick about a gambler who isn’t addicted to the adrenalizing power of placing bets as much as he is to failure. If Digging for Fire is essentially a retread of Mazursky’s 1969 comedy-drama masterpiece Bob & Carol & Ted & Alice, then Win it All is a riff on May’s Mikey and Nicky, a gritty, off-kilter buddy flick that mines humor by way of gangland danger. But May made films, and Mazursky made films, while Swanberg, bless his unfailing tenacity, appears to get behind the camera and hope everything works out for the best. (His films, appropriately enough, often feel like gambles unto themselves, improvisational products that eschew traditional elements of craft like, say, scripts.) His style is chancy, but it’s hard not to admire his unabashed love of spontaneity.

This is especially true when it does work out for the best, as it does in Win it All. Swanberg co-wrote the film with your underachieving dream boyfriend, New Girl’s Jake Johnson, ostensibly a direct result of their actor-director collaborations in Drinking Buddies and Digging for Fire; Johnson, perhaps unsurprisingly, is the star here, too, playing that aforementioned scruffy gambler, Eddie, a career loser who takes any wager-earning gig he can get by day before flinging his earnings down the crapper playing games of chance at incalculably grimy casinos by night. The film is wrapped around him but Swanberg’s character study is supplied a backbone via temptation. Early on, one of Eddie’s unsavory acquaintances, who’s readying for a 6 month stint in prison, makes our foolhardy hero a literal offer he can’t refuse: Hang onto a duffel bag stuffed full of cash, and make $10,000 when the term is up. Easy money.

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But not as easy as the money that’s in the bag itself, which Eddie, against the furious advice of his long-suffering Gamblers Anonymous sponsor, Gene (Keegan-Michael Key), quite happily and quite liberally borrows from to feed his habit. Eddie wins a couple grand using the ill-advised loan, and while coming down from his hot streak romances Eva (Aislinn Derbez), an endlessly charming single mother he bumps into at the bar he frequents with his pals. We snap back to reality immediately after as Eddie overplays his hand and ends up in a real hole, wasting many more thousands of his associate’s money, which in the movies is the sort of idiot move that puts a person in mortal peril.

There is, in grand Swanberg tradition, a looseness to Win it All that remains for the duration of the film, hanging off of Johnson’s central performance. Whether because of his contributions on the page or on the screen, Johnson feels like a key component to Win it All’s success as a narrative: The story hangs off of him, off of his work, his emoting, the physical quality to his self-presentation before a lens. You wonder if maybe Eddie is a version of Johnson himself, spun out of the experience one gains from struggling with their worst merits. (This, it must be said, is speculative, but worth pondering all the same.) He gives Win it All a framework that Swanberg traditionally veers away from, and though the movie bears hallmarks of ad-lib directing, Johnson’s steadfast reliability keeps it on the rails throughout.

It means a lot that Swanberg and Johnson both care on a profoundly human level for Eddie. Who couldn’t? You probably have an Eddie figure in your life, whether you know it or not: The gregarious, amiable rascal, the kind of dude who just can’t slam the brakes when he’s careening toward trouble and knows it. He’s a lovable schmuck, his own worst enemy. The people in his life—Eva, his friends, Gene, his brother Ron (Joe Lo Truglio, ditching his sad puppy routine for a more grown-up look)—care about him, his creators care about him, and so of course we care about him, too, even at his worst, even as he invites troubles and hazards into his life against all fair warnings given him by his support system.

Win it All, in other words, is a Joe Swanberg movie, a domestically-focused tale about a slacker in conflict with his demons washed in the texture of 1960s and 1970s cinema. (Aside: If not for hints of modernity, a’la cell phones, we might guess that Swanberg’s setting is period instead of contemporary, which adds yet another layer to his fondness for both eras in cinema’s history.) It’s also further evidence that his relationship with Netflix, which first blossomed last year with his TV series Easy, is quite possibly the best thing to happen to him since Drinking Buddies, providing him with a wide-open space where his evolving, exploratory aesthetic can thrive. But the film is foremost an object lesson in identifying the intangibles that separate good Swanberg from bad Swanberg. Maybe he doesn’t need the right screenplay, but he does need the right actor.

Director: Joe Swanberg
Writer: Joe Swanberg, Jake Johnson
Starring: Jake Johnson, Aislinn Derbez, Joe Lo Truglio, Keegan-Michael Key, Nicky Excitement
Release Date: April 7, 2017

Boston-based critic Andy Crump has been writing about film and television online since 2009, and has been contributing to Paste Magazine since 2013. He writes additional words for The Playlist and Birth. Movies. Death., and is a member of the Online Film Critics Society and the Boston Online Film Critics Association. You can follow him on Twitter and find his collected writing at his personal blog. He is composed of roughly 65% craft beer.