Andy Karr’s review published on Letterboxd:
Swanberg could easily (har har) lean back and coast through endless plotless iterations of Jake Johnson: the Motion Picture, and fans of that, myself included, would probably be content. It’s so refreshing and cool that he’s pushing himself to do more. Win It All is an excellent character study, following the effervescent Johnson as a recovering gambling addict through romance and relapse in a gritty, working-class Chicago. It’s both a fun hang, like all Swanberg movies, and fully plot-driven in a manner akin to more mainstream storytelling.
More like this please, Joe. Maybe spend more time with the women in the next one? But yeah, really good.