Dave Jackson’s review published on Letterboxd:
It makes me a bit sad when people shit on Joe Swanberg. It seems that there's this idea that he tricked his way into filmmaking and lucked out by being there at the right place at the right time. That his films are lazy. Devoid of anything resembling "cinema". Whatever that means. Surely there's room for all kinds of filmmakers? If Swanberg is lazy and shit, does that mean someone like Éric Rohmer was lazy and shit? (I'm not saying Swanberg is on the same level, just that they're both restrained in their approach.) As someone who dabbles in film, I wish I could make films like Swanberg. There's a bravery to the quietness of his work. That said, Win It All is definitely the most "cinematic" of Swanberg's work. The camera moves a lot more than usual (the cinematography is gorgeous actually). There's definitely a solid script this time round. But, despite the shine, it still contains that same uncomfortable honesty of his earlier work and Swanberg's knack for presenting realistic relationships. Jake Johnson is fantastic in the lead, making a likable character out of a frustrating gambling addict. Aislinn Derbez is also incredibly charismatic. A surprising addition to Swanberg's talents is how tense he manages to make Win It All. This is a stressful film, beautifully using titles showing how much money is being lost in each gambling adventure to ramp up the terror. The tension is swept away for a simple, gentle ending that really got to me. I think this is perhaps my favourite Swanberg so far.