Goes straight to my " feel good " movies list. its very simple, yet touching. I smiled almost the whole time. actors were brilliant and everything felt natural and not overacted. if you like happy ending movies, but not the cheezy kind, this movie is for you. 10/10

For some reason I just didn't like this film as much as most of Swanberg's output. Straighforward plot is just not what he does best, his strong suit has always been character study, and with this film his characters were all sort of one dimensional; even the main character, though more rounded, falls a bit flat. I just feel like the story did not fit well with Joe Swanberg's easy mumblecore style, and felt a little forced.

"Win It All" is a film about a guy who is floating through life, never accepting responsibility. He is also a gambling addict, which is partly to blame for his lack of maturity. He knows he needs to reform, but he cannot muster the willpower. Like most gamblers, he is always waiting for the big payoff to pull him out of his hole, and fate sends him an opportunity to regain fiscal fitness--if he can just control his impulses.This is a solid kernel of an idea for a film, and Jake Johnson feels committed to the part of the main character, Eddie, but the film never reaches its potential. Much of the story feels clichéd and the characters are underdeveloped. This is most noticeable with Eddie's romantic relationship--with Eva (Aislinn Derbez, who feels like she has more to contribute). The development of their feelings for each other is cheated by many brief scenes that sometimes feel like a montage. This may be due, in part, to editing, but the writing is the main culprit. In scenes that should carry some weight, there is inadequate exposition. It's like watching a Cliff's Notes version of a film.The ending is abrupt and underwhelming. It's unclear if this was intentional or if it was due to the inadequate build-up of dramatic tension.

Netflix said I will give this a full score. Netflix was right. This is a film about a man who has no job and no prospects. He thinks he is a good gambler but he is not good at all. A friend/colleague is going to prison. The guy leaves the protagonist a bag and says in clear terms, don't open it. I'll take it back when I get out and give you $10k. Our protagonist agrees. But he can't help him self.What follows is a funny, entertaining and hilarious ride. I loved this. This is like an Indie Swingers. This is Jake Johnson's best film since drinking buddies which I really liked. Raw and edgy. Fans of Rounders + Swingers + Owning Mahowny may appreciate it. Whereas Louis Ck fans might wanna try it too. Why am I writing this review? The rating on IMDb is ridiculous and discouraging