"I want you to repeat after me: 'my name is Eddie, and I am a loser. I am addicted to losing.'" So says the sponsor (Keegan-Michael Key) of a Chicago gambling addict (Jake Johnson). Eddie Garrett knows he's a bum – parking cars at Cubs games before going out and playing poker all night, he's not so much chasing the high of winning as he seems to enjoy the ass end of the barrel. He's comfortable there, wallowing in filth and just scraping by. Eddie’s got a brother (Joe Lo Truglio) who cares about him and keeps begging the deadbeat to come work his way up the ladder at his landscaping business. But Eddie is content to keep bottoming out, as writer/director Joe Swanberg (with the help of his now three-time multi-faceted collaborator, Johnson) crafts possibly his most complete character in the flat out funniest movie of his career, Win It All.
While the above description may sound like an utter bummer – revisiting the unglamorous gutters the likes of which The Gambler’s Axel Freed once called home – Swanberg's approach is more like a drunken hangout take on Rounders. Like his previous breakout from the usual lo-fi mumblecore milieu, Drinking Buddies, Swanberg is more interested in observing his characters as they interact over beers and joints, sweating out their problems before waking up hung over and wanting to do it all again. There's certainly a plot; involving a bag of money left for Eddie to watch while his bookie (José Antonio García) goes off to the clink for six months with promises of a $10,000 pot of gold at the end of this shit-smeared rainbow. But Swanberg is again setting up scenarios in which we learn to empathize with this born loser, even as he digs a hole for himself in the middle of Wrigleyville by gambling the thug's ill-gotten gains away. All he had to do was not open the satchel, and we scream this at him as Swanberg’s cringe comedy ratchets to unbearable levels of hilarious tension.
Johnson and Swanberg's partnership has turned into quite the mutually beneficial endeavor. As an actor, Johnson's evolved under the indie auteur into a slimy charmer who you'd let play with your kid, but never really consider allowing him to babysit. There's a layer of grease that covers Johnson at all time, just as there was a sheet of sweat that coated him during the entirety of Drinking Buddies. He physically manifests each character's defining characteristic, to the point that you can practically smell the gambler's cheap cologne and unclean body after a night spent in a back alley poker den. At the same time, Johnson is almost effortlessly entertaining, diffusing even the edgiest of situations with a goofy facial tic. He's a truly gifted performer, taking the comedic chops he honed on network TV and transmuting them to fit perfectly with Swanberg's naturalistic approach to character development. Though when Eddie is pushed or has his sense of responsibility challenged by Lo Truglio's equally realized sibling, he snaps back and shuts down. He's not stupid. He knows he's a fuck up. But that's for Eddie to deal with in his own way. He doesn’t need anyone else to impose some bullshit familial mandate. This is a real human being Johnson and Swanberg have created, and (depending on your walk in life) you've more than likely known an addict like Eddie at least once.
Behind the camera, Swanberg retains his usual drifting sense of mis en scene; the ruddy lo-fi aesthetics he's been toying with ever since his days shooting and cutting on a laptop merely refined instead of compromised. However, where scenes in his previous endeavors either felt rushed or left lingering for one beat too long, the filmmaker’s sensibilities as an editor have never been sharper. Each scene in Win it All unfolds with purpose, driving Eddie's narrative forward in one way or another. When the addict decides to shape up his life and take his brother up on the job offer in order to "get his shit together", Swanberg doesn't just skip through this via a flighty montage. Instead, he pays close attention to Johnson's choices as a performer, utilizing takes of half-scripted/half-improvised scenario work that contain truly fascinating moments of tiny human interaction. Likewise, he gives those Eddie bounces off of the chance to have their own, real reactions to the growth he's experiencing as a person. Win it All is Swanberg's tightest movie, and no doubt his most accessible; the directing/writing/performing duo having discovered a true rhythm and shorthand together that's magic when it works.
With his continued move toward more traditional storytelling, Swanberg experiences some growing pains of his own – namely that his two main plot threads hinge on rather large suspensions of disbelief. First off, the notion that a small time criminal would leave a large sum of cash in the care of a man everyone in the neighborhood knows to be an utter junkie is, frankly, a load of horseshit. Similarly, it's rather difficult to buy into his love interest, Eva (Aislinn Derbez) - a working single mother who also cares for her madre in the suburbs - ever really falling for this oily slickster, charming as he may be. But if you can accept the reality of this otherwise lived-in cinematic experience, Win it All proves to a rather satisfying comedy that ties itself up just a little too neatly. Nevertheless, we're all rooting for this lovable scumbag by the end, hoping everything will turn out OK, even though it probably shouldn't.