When Joe Swanberg emerged in the mid-’00s, his approach to filmmaking was downright refreshing. Working with unbelievable speed and emphasizing improvisation, the writer/director’s films were small, actor-driven, and—sorry, but there’s no other word for it—quirky.
As Swanberg’s matured and gained an audience, his films have, perhaps necessarily, bent toward conventionality. There are pros and cons to that development, and his newest, the Netflix-released Win It All, is evidence of both. Centered on a luckless loser played by Jake Johnson, Win It All trades in the appealing, interlocking, Altman-esque aspects of Swanberg’s series Easy to focus intently on a single character. In that respect, it’s a total success—due in no small part to Johnson’s easygoing, transparent performance—but at the film’s close, it all feels a bit pat.
Things start ominously, if predictably. Eddie (Johnson) is a gambling addict who can’t get his life on track, but two strokes of fate land in his lap: He meets a woman he really likes (Aislinn Derbez), and a shady acquaintance asks him to hold onto a bag full of money. For someone who’s got his shit together, these would be great developments. But Eddie crumbles, and with the help of his kind but overbearing brother (Joe Lo Truglio) and his skeptical Gamblers Anonymous sponsor (Keegan-Michael Key), he tries to keep his life from blowing up.
Unfortunately, there’s a bleaker, seamier story here that never seems to fully materialize: As Eddie correctly realizes by film’s end, he’s not so much addicted to gambling as he is to losing. But while we sense he goes to some dark places, Swanberg and Johnson’s mutual love for Eddie prevents the audience from seeing them. Instead, Win It All wants to play nice and warm hearts. It wants you to win, too.