Is there a more destructive addiction than gambling? Instead of a mere hangover, compulsive gamblers can find themselves deeply in debt to leg-breakers. Eddie Garrett is exactly that sort of loser. In fact, his Gambling Anonymous sponsor tells him straight out he is addicted to losing. When Garrett really, really gets in over his head, he finally starts to clean up his act. However, just as he starts to appreciate the straight life an enormous karma bill come due in Joe Swanberg’s Win It All (trailer here), which debuts on Netflix this Friday.
Garrett is in debt to just about everyone, except Michael, the scary looking criminal waiting for him in his apartment. Instead of a painful collection, Michael is there to offer him an easy gig. While he is serving a short prison term, Garrett will babysit a mysterious duffle bag. As long as he resists temptation, he makes an easy ten grand when Michael returns.
Of course, the bag is stuffed with cash, as well as other rather ominous looking implements. It is just as certain Garrett will peak inside and start using the money to fund his losing streaks, despite his sponsor’s best efforts to talk some sense into him. Garrett will have one lucky night with the duffle bag money, so naturally he celebrates with his schlubby buddies. As fate would have it, he also meets Eva, an attractive RN, who should be way out of his league.
True to form, Garrett subsequently starts to lose Michael’s money, to the tune of $20K or so. The repercussions of this potential shortfall are sufficiently dire to scare him straight. He accepts a job at his brother’s landscaping company and finds he almost enjoys working like a responsible adult. Concurrently, he manages to develop a serious relationship with Eva. However, all his progress might be for naught when Garrett learn Michael Duffle Bag will be getting out of prison months early.
Even though WIA has an appealingly grungy, lived-in vibe, it is light years more polished than the early Mumblecore that initially made Swanberg’s name. Essentially, he and Jake Johnson, his recent co-writer and star of choice, have combined the rom-com with the gambling caper. Yet, unlike Rounders and scores of card-sharking films, they really see redemption in everyday, responsible life. Having a job and a girlfriend (especially a gorgeous one) are good things. They also shrewdly use the gritty streets and back alleys of Chicago as vivid backdrops.
Johnson is terrific as Garrett and he develops winning chemistry with all the major players. Mexican actress Aislinn Derbez is utterly charming, but completely grounded as Eva, the single-mother nurse he really doesn’t deserve. Johnson and Joe Lo Truglio bicker and kvetch together so convincingly, we can totally believe they are brothers with years of difficult shared history together. However, the funniest scenes focus on Garrett trying to fast-talk his undeluded sponsor, played with acerbic attitude and surprising gravitas by Keegan-Michael Key (in what might be his best dramatic performance to date).