Win It All is concerned less with gambling addiction and more with the power of losing. You go in with the highest of intentions, all the necessary wherewithal to play a great hand, and in one fell swoop lose it all. That’s not an explanation of the gambling vice; that’s Win It All.
The parts are great: Joe Swanberg has form as a writer/director (Drinking Buddies, Digging for Fire), his cast is a veritable who’s-who of should-be-bigger small part players, and the plot has great comedic-drama potential. But all of this just gets flushed away.
The weirdly attractive Jake Johnson plays great losers, and Eddie is no exception. He plays the highs and lows well, giving the character a sense of realism. A scene comprised almost entirely of him saying “oh no” on repeat is a standout showcase of his comic charm. The supporting cast too, most notably Joe Lo Truglio, Keegan Michale-Key and Aislinn Derbez, are for the most part fun to watch.
Where the film folds is in the delivery. Even at 90-minutes, it feels stretched thin – there’s plenty to like here but it’s going nowhere and going there slowly. Heavy reliance on gambling cliché and a liberal dose of lucky coincidence strips the film’s tone of truth.
An inconsistent tally of Eddie’s monetary ups and downs proves little more than a distraction or rough afterthought. More regular use of it would have been amusing, although getting rid of it entirely would not be to the film’s loss.
Shot using the grittiest celluloid available, Win It All could have been a darkly comic addiction study. In the end, Win It All is akin to that “Indiana Jones didn’t have to be in Raiders” theory. Maybe Eddie learnt something about himself in those 90 minutes, but we certainly didn’t.
CAST: Jake Johnson, Rony Shemon, Morgan Ng, Edward Kaihatsu
DIRECTOR: Joe Swanberg
WRITERS: Jake Johnson, Joe Swanberg
SYNOPSIS: Eddie Garrett (Johnson) agrees to watch a duffel bag for an acquaintance who is heading to prison. When he discovers cash in the bag, he’s unable to resist the temptation and winds up deeply in debt.