A more lovable loser there may not be than Jake Johnson’s Eddie Garrett in Win It All. The 18th (!!!) feature from mumblecore originator Joe Swanberg, Win It All is the second “official” collaboration between Swanberg and Johnson, who paired up last year to middling success with Digging for Fire after previously working in a director-actor capacity on festival favorite Drinking Buddies. Swanberg’s brand of low-key, grounded comedy-drama has rarely been better than in Win It All as he and Johnson create an emotionally involving character study of a man whose addiction to gambling (and losing) has come back to bite him, just when life has started looking up.

A garish rogue in his own mind, Eddie Garrett’s life is a lot less glamorous than he imagines. He parks cars at Cubs games between bouts of late night drinking with his buddies, which often leads to sketchy underground poker clubs where Eddie absconds to flush his money down the drain. He may dress in horse track whites, wave Benjamins and cheer on his stead but Eddie, for all intents and purposes, is nothing if not a guaranteed losing bet. When a not-so-savory “friend” recruits Eddie to watch a mysterious duffel bag as he serves a 6- to 9-month prison sentence, the gambling low life with a heart of pewter seems to have caught a huge break.

All he has to do is sit on the bag and not look at its contents and he’ll find himself $10,000 richer. That’s it. There’s no hoops. No shady deliveries. Just a high paying storage job. Easier money earned may not exist. Not one for self-control, Eddie becomes the proverbial cat whose curiosity got the better of him and peeks in. He discovers the bag is loaded of cash. Also a rather forbidding hangman’s rope. The imagery is suggestive, likely the arrangement of his imprisoned contractor. Money and life (or death as it were) itself are bundled; a pricy package deal. Being a drunken fool with a bad habit, Eddie promptly gambles a large chunk away (around $20,000) and must come up with a way to get the money back lest he wind up in a ditch, split ear-to-ear.

The situation is complicated by the arrival of new romantic interest Eva (Aisling Derbez), a night nurse who (by no fault of her own) tempts Eddie to the light side. As Eddie attempts to recover the money the good old fashion way – work – he takes up with his brother Ron’s (Joe Lo Truglio) landscaping company, learning the meaning of hard work and surprising himself with how much he enjoys the accompanying stability. The relationship sprung between Eddie and Ron is, for lack of a more descriptive term, nice. Because Win It All, for its potentially sour notes and grounded harsh realities, is to its very core a “nice” movie; it just makes you feel pretty damn good.

Swanberg and Johnson don’t fall for the gambler’s fallacy and unlike Eddie, they don’t leave the odds to chance. Unlike most of Swanberg’s collection, Win It All works for a fully functioning script. Like one with pages. Dialogue. And, gasp, blocking. Fans of Swanberg will know the man typically writes a few pages of treatment – general plot points, through lines and character arcs – allowing his actors to find the dialogue in the moment. That is not the case here and for it, we are witness to an evolution of the oft freewheeling director.

The cast is great from head to heel but none supersede the phenomenal work Johnson offers. His performance is richly textured, layering snide comedy, adorable romantic impulses and a looming sense of fear of consequence that haunts the darker corners of the screen. But Swanberg never lets Win It All seem too glum. Even in Eddie’s great moments of despair, his sponsor (he used to go to meetings for his gambling problem, not alcohol, though it could easily be argued that wouldn’t hurt either) played by Keegan-Michael Key openly laughs in his face.

The balance between those two impulses – great human tragedy boiled into an almost Shakespearean comedy – is played with throughout and the result is nothing shy of delightful. A scene where Eddie’s body literally rebels against his addictive urges is the laugh out loud pinnacle of that discord, amplifiying the chord of bittersweet imperfection that Swanberg and Johnson have so masterfully conjured.

CONCLUSION: Joe Swanberg’s redemption story of a lovable loser is equally parts humanistic hilarity, endearing romance and dramatic thrills where Jake Johnson shows the smug charm that makes him so watchable in ‘Win it All’ a comeback tale that’s as winning as they come.


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