Kevin Jones’s review published on Letterboxd:
Pure mumblecore, yet scripted beyond what is typical for a Joe Swanberg film, Win it All also happens to be Swanberg's best film yet. Putting him alongside Jake Johnson yet again, the film stars Johnson as Eddie Garrett. A degenerate gambler who is asked by a friend to watch a bag full of money, he naturally gambles it all away and must earn it all back before the friend gets out of jail. Yet, coinciding with this, he tries to fix his life with new girlfriend Eva (Aislinn Derbez) lighting his fire again, brother Ron (Joe Lo Truglio) giving him a job in the family landscaping company, and his sponsor Gene (Keegan Michael-Key) offering him advice and guiding him through his rehabilitation. A loosely plotted film, it has echoes of other gambling-centered films, particularly Robert Altman's California Split for how the film just focuses on these gambling addicts going about their daily life as addicts. Yet, Win it All switches it up by making this a compelling character study of a man that wants to change and gets the audience to root for him, no matter how many bad choices he makes.
Initially making all the wrong moves, Eddie rejects a job offer from his brother and continues to gamble compulsively. It is only when he loses the money of somebody whose money should not be lost does he actually begin to change. However, until then, he is a largely detestable character. It is clear that Swanberg has learned from films such as Happy Christmas where the self-destructive nature of the central addict character is repulsive and leads to a film that gets chastised for having such an unlikable protagonist. Win it All begins much the same way as that film with Eddie hanging out with his settled-in and high-achieving brother and his family, divulging just how destitute his situation is and expressing his hopeless dreams and falsehoods about his current lifestyle. Watching him lie and then go out and gamble all night yet again is a tough cycle to watch and one that makes us inherently want to root against him and just be put to a stop.
Yet, Swanberg manages to make him incredibly sympathetic. We see him fail, but having him meet Eva when at a gambling high and right before a big fall shows the stakes put before him. He must put together his life and quickly if he wishes to have this great girl in his life. This gives the film good stakes, but also makes him more likable and a guy that you root for. Prior to this, he was hurting just himself. Now, we want to see him succeed to not hurt somebody else. Scenes of them together or him hanging out with family as he recovers from gambling all point to this same aspect of the film. As he changes from being unlikable to an impeccably sympathetic man, we want him to succeed and be happy at the end. When things begin going wrong, our heart breaks for him and want to see him put it back together again. Yet, in this character study, Swanberg does misstep. While largely just a look at the life of Eddie and shot and written incredibly realistically, the ending feels like movie fantasy. It dispatches of the low-key mumblecore stylings of the film and embraces a more commercial dramatic ending akin to Rounders or another gambling film when Eddie sets out to win back all of the money. It is unfortunate for a film that is such an intimate look at gambling addiction made by a director who is unafraid to just let them things happen and not script them, only for it to u-turn and become incredibly scripted and cliched at the very end.
As a comedy, the film is mostly focused on telling jokes. Instead, it presents real life scenarios and finds the comedy in everyday life. Encounters between Eddie and his brother Ron really show as this enjoy family life or just mess around with each other as friends and brothers do. Yet, the comedic highlight of the film is Keegan-Michael Key. Absolutely hysterical in his role as Gene, his character is casually funny without really trying and brings a lightness and great comedic zip to the film at all times when he is on-screen. As a foil to Johnson's more serious and downtrodden characters, Key's loose and supportive sponsor role is perfection.
A funny and engaging character study, Win it All becomes a bit too scripted and conventional in its climax and third act, but until then, it is a loosely put together and highly unique film, even if it still falls into the mumblecore genre of filmmaking though with a bit more structure than usual. With this added structure, Swanberg shows that these stories about lost 20-30 somethings can find an aim and serve a purpose instead of just being an hour and a half of characters walking around and driving themselves further down in the pit of despair. For this reason, Win it All is certainly the biggest win of Swanberg's career, even if it needs some additional polishing.