Win It All marks the third collaboration between director Joe Swanberg and actor Jake Johnson, as well as their second as a writing team after Digging For Fire, and it is undeniable that the pair have a cinematic kinship that immediately makes their efforts intriguing.
In Win It All Jake Johnson plays Eddie Garrett, a small-time gambling addict who's unable to get his life together because of his affliction. His efforts to do so are waylaid even further when an old friend who's about to be sent to prison asks him to look after $50,000, which Eddie immediately starts to work his way through. It's at this point that Eddie realizes he has a problem, and with the help of his sponsor Gene (Keegan-Michael Key) and brother Ron (Joe Lo Truglio) he looks to get his life in order, even starting a relationship with a single mother Eva (Aislinn Derbez). However the debt and his urge to gamble is never far away, especially when his pal's prison sentence is shortened.
There's an effortless charm and warmth to Jake Johnson that makes him perfectly suited to such lo-fi fare. Joe Swanberg knows that, too, giving the actor the freedom and time within the frame to strut his stuff, and trusting that Jake Johnson has the audience in complete control, while also positioning him to create an instant mood or emotion in just a single shot or with a look, too. Because of Jake Johnson's amiable persona, and the fact that Win It All presents Eddie Garrett as addict that's down on his luck and trying to perverse, you're always on his side and rooting for him to come through.
So much so that you can't help but be lulled in. Especially as Joe Swanberg and Jake Johnson do such an impressive job of establishing how much Eddie Garrett's close friends and family look down on him at the start, before then showcasing Eddie's high as he goes on a winning streak with the money that's not actually his. In these moments, as Eddie buys drinks for everyone and Johnson releases a palpable sense of hysteria, you really fall for the character.
Of course, in a film of such ilk, what comes up must go down, and Eddie Garrett overextends himself and soon starts to lose. Badly. As Eddie Garrett's losing streak spirals out of control, Joe Swanberg hides the ticker that had previously been revealing exactly how much he'd won until the very last moment, where, after a prolonged montage of defeats, it's tragically revealed that he's $20,000 down. The fact that this defeat is so impactful, and such a punch to the gut for the audience, speaks volumes of the connection that Johnson and Swanberg have built. At this moment Win It All hasn't really made a foot wrong, which makes it all the more disappointing that it can't build on this momentum.
It's not that Win It All particularly nose-dives into tedium. It just plateaus. In a way it's understandable, as at this part of the movie Eddie Garrett looks to get on the straight and narrow, and the innate excitement of his gambling exploits flitters away. The emergence of Joe Lo Truglio and Keegan Michael-Key helps. Plus there's also a couple of particularly funny scenes involving Eddie and his pals trying to figure out how he can get out of his predicament and Eddie and his incompetent bag-man at a high stakes game, but the detailed characterization and commotion of its opening gives way to a relative simplistic final two acts and ending, which lacks a punch.
Despite these flaws, Win It All is another reminder that Jake Johnson and Joe Swanberg are a potent and dynamic filmmaking team that are willing to explore seldom seen complex characters in a refreshingly honest fashion. And even though Win It All does tail off, long may that continue.