Tyler’s review published on Letterboxd:
Swanberg doing a genre film? Not exactly. It's still basically a dramedy, though unsurprisingly, it feels hindered by its genre elements.
Jake Johnson is great as always (as ALWAYS) and it's shot beautifully on 16mm. An easy to love film, with its only true mistake being that it isn't about much. Win It All has none of the coherent, meaningful qualities that Swanberg's latest (and best) film, Digging for Fire, had, but it's still a blast.