Win It All (2017) / Comedy-Drama
MPAA Rated: Not rated, but would likely be R for language
Running Time: 88 min.
Cast: Jake Johnson, Joe Lo Truglio, Aislinn Derbez, Keegan-Michael Key, Steve Berg, Jose Antonio Garcia
Director: Joe Swanberg
Screenplay: Joe Swanberg, Jake Johnson
Review published April 21, 2017
Starting with the old-as-cinema premise of the trouble that ensues when someone finds a duffel bag full of cash, then top that with another oft-told feature of a guy with a gambling addiction who just can't stop himself from losing it all, micro-budget director Joe Swanberg (Drinking Buddies) and co-screenwriter and star Jake Johnson (Mike and Dave Need Wedding Dates, Jurassic World) take what's considered passť and make it their own thing, in this Netflix original movie.
Small-time gambler Eddie Garrett's life is on the skids. No wife or family, no steady jobs, and, thanks to his incessant compulsion to gamble, no real income to support him. Eddie's brother Ron (Lo Truglio, Pitch Perfect 2) wants him to find steady work and join him in helping out with the family landscaping business, but Eddie would rather walk down Easy Street and (hopefully) catch a lucky break at the poker table that will keep him rolling in dough for a while.
When a mysterious duffel bag is literally dumped on his lap from a convict friend named Michael (Garcia), who offers him ten grand to keep an eye on it while he serves a six-month stint in prison, he readily accepts the easy-peasy offer. When he also meets what might be the woman of his dreams in a bar one night, a single mother who works daily shifts at the hospital as a nurse, everything seems even grander than the ten grand. That is until Eddie feels that familiar itch once he looks in the bag and discovers a bundle of several wads of cash just waiting to be played at the gambling tables.
While Win It All may not have high cinema ambitions, there's a watchability factor that remains in play for those who enjoy comic characters interact in a variety of mostly improvised scenarios. Although it is about a man struggling with an addiction at its core, and he has tried to get help in terms of being in a program that seeks to cure people of such addictions (represented by Keegan-Michael Key (Don't Think Twice) as his skeptical sponsor Gene), this is not a heavy-handed drama about the dire crises that can occur to chronic gamblers when they go too far. Certainly, the film offers up ramifications for actions, one of which includes the possibility that Eddie will have to run for his life should he not have all of the money expected in the bag once the convict is released, but Swanberg keeps the tone light and comical, even if we do have a palpable sense of what tragedies might befall Eddie should he screw up his life even more.
Nevertheless, while this isn't a "lesson movie" full of maudlin, cautionary tropes, there is a theme here that is uplifting, about how a sense of self-worth is fulfilling beyond an easy payday, and how good it feels to work hard to have something, whether through putting ones nose to the grindstone with blood, sweat and tears, or through waiting patiently for the right woman to be able to open up her heart and home to the possibility of more. It's a film that shows that the adrenaline rush of having one's livelihood on the line gets much more complicated when you stack more things one can lose on the other side of the scale -- love, career, a future, and even one's own life. Some things are beyond monetary value, and we hope that Eddie can see this in the tug of war between his high and his heart, which is something that gets a metaphoric expression within the film in a literal way.
©2017 Vince Leo