'Win It All': Film Review | SXSW 2017
Jake Johnson struggles to resist temptation in Joe Swanberg's Chicago-set gambling picture.
The most convincing of the three features Joe Swanberg has made with star and co-writer Jake Johnson (each of which has represented a highlight in his filmography), Win It All should come with what is now called a trigger warning: Gambling addicts may respond poorly to this tale of a poker player who gets in over his head, decides to reform, and thereafter struggles to resist an opportunity he'd be an idiot to exploit. Where their previous collaborations have been star-heavy affairs seemingly designed to expand the indie auteur's audience, this outing relaxes, using a choice couple of familiar faces extremely well and focusing on getting its sense of place right. The result will play well on Netflix to fans of the director and star; SXSWers are lucky to see the celluloid-shot effort on the big screen.
Johnson stars as Eddie, an on-the-margins character who works just as much as necessary to fund all-night sessions in illicit poker dens. He's in the hole when a jail-bound acquaintance offers him a job: Take this bag, don't look inside, and keep it safe until I'm home in six to nine months; I'll give you ten grand for the favor when it's done.
Once alone with the duffel, Eddie lasts about as long as you'd expect trying not to open it up. There's an enormous amount of cash inside, and Eddie puts up enough semblance of a fight that he sets a meeting with his Gamblers Anonymous sponsor — Keegan-Michael Key, a reliable source of "don't ask me to buy your self-delusion" comic relief — to ask for advice. There would be no movie if Eddie heeded that wisdom, though, so soon we see the bag come out of the closet and the text "-$500" flash onscreen.
We know that silent counter will soon show more frightening in-the-red sums. But before it does, Eddie enjoys some luck. While celebrating a good night in his favorite dive, he meets Eva (Mexican actress Aislinn Derbez, who appeared in Swanberg's series Easy); the two walk and talk all night, bolstering Eddie's sense that he has turned his life around. The next day he puts on his high-roller suit, heads to the racetrack, and rides that self-confidence into the dirt.
It's here, with Eddie owing over $21,000 to the bag and its felonious owner, that Win It All diverts from the expected genre path. Shaken and genuinely remorseful, Eddie finally takes his big brother (a very sympathetic Joe Lo Truglio) up on his offer to join the family landscaping business. He sets his alarms, wakes early and slaves away without complaint. He woos Eva, respecting her desire to take things slowly. He seems likely to remake himself into a real salt-of-the-earth lucky guy, paying off his debt in tiny installments before his friend gets out of jail and learns he has been robbed.
Armchair screenwriters will see where this is going. But fewer will anticipate exactly where the impending complications swing the plotline, which is why discussing the problems therein should be left for post-viewing conversations. Suffice it to say that what satisfies on one level raises questions on others, and that certain plot points mightn't play as well without someone as charismatic as Johnson putting them across. Win It All becomes a gambling picture that subverts the usual morality-play stuff, or simply decides it knows better, and therefore will win no awards from addictive-personality support groups. But for once, it's a life-on-the-fringes flick in which the goal of going straight — often a red herring in these films — looks genuinely appealing.
Production company: Garrett Doubles Down
Cast: Jake Johnson, Aislinn Derbez, Joe Lo Truglio, Keegan-Michael Key
Director-editor: Joe Swanberg
Screenwriters: Jake Johnson, Joe Swanberg
Producers: Jake Johnson, Joe Swanberg, Alex Orr
Executive producers: Peter Gilbert, Eddie Linker
Director of photography: Eon Mora
Production designer: Aimee Holmberg
Composer: Dan Romer
Venue: South by Southwest Film Festival (Narrative Spotlight)