In the 12 years since Joe Swanberg released his debut feature, Kissing on the Mouth, he has emerged as one of America’s finest filmmakers, with a vast and varied filmography. One major facet of the wonderfully rich tapestries Swanberg’s works represent is the collaborative nature of his filmmaking process. Unlike many directors, he regards his actors as co-equal creators, making extensive use of improvisation and often giving them co-writer credit.

In recent years, Swanberg’s most fruitful collaboration has been with Jake Johnson, best known for the Fox sitcom New Girl. Previously, they worked together on Drinking Buddies and Digging for Fire, and with Win It All, they have come up with yet another beauty, a film which transforms extremely familiar genre elements into an infectiously comedic movie full of vividly detailed portraits. Swanberg and Johnson’s third collaboration—they co-wrote and co-produced—continues a potent creative winning streak, in sharp contrast to the track record of the hapless gambling addict Johnson portrays.

Win It All is thematically similar to Swanberg’s three previous features (including Happy Christmas) in that it features a protagonist confronted with the choice of embracing full adulthood—along with the maturity and responsibilities that entails—or continuing to operate in a state of arrested development. Eddie Garrett (Johnson) is an unrepentant gambling fanatic, putting all of whatever money he makes working odd jobs on the line at underground casinos in Chicago’s Chinatown.

Eddie loses far more often than he wins. As such, he exists in a precariously marginal fashion, always on the edge of financial collapse, looking over his shoulder in fear of running into various people he owes money to. His family and friends—including his older brother (Joe Lo Truglio), sister-in-law (Kris Swanberg), and Gamblers Anonymous sponsor (Keegan-Michael Key)—urge him to change his self-destructive path, to no avail.

Suddenly, an old acquaintance, Michael (Jose Antonio Garcia), shows up with the proverbial offer Eddie can’t refuse. Michael asks Eddie to keep a duffle bag in his apartment while he does prison time for about six months or so, with strict orders for Eddie not to open the bag. If Eddie follows through, Michael promises a reward of $10,000 when he returns; Eddie accepts without an ounce of hesitation.

Predictably, curiosity gets the better of Eddie, and he opens the bag. Buried under some ominous-looking metal tools and gnarled rope is a huge amount of bundled cash. Anyone who’s ever seen a movie can easily guess what happens next and know this can’t end well. So, of course, Eddie starts gambling with the money. And, again of course, he falls deeply into debt, tracked with an onscreen tally of the amount he currently owes Michael, a sum that quickly grows to a frighteningly large number.

Like many addicts, Eddie eventually arrives at the come-to-Jesus realization now that he has hit rock bottom and decides to straighten up and fly right. He goes to his older brother and offers to work for him at their late father’s landscaping business, a job that he has refused for many years, to earn back the money he lost gambling. To his surprise, Eddie finds great satisfaction in manual labor and earning a steady paycheck. To sweeten the deal, Eddie meets Eva (Aislinn Derbez), a nurse and single mother whom Eddie can envision settling down with.

Unfortunately, fate takes an extremely cruel turn, and just as things seem to be coming together for Eddie, they very quickly fall apart: Michael calls Eddie from prison and informs him that he’s getting released early and will be home in a few days. (The wide-eyed expression on Eddie’s face as he gets the news is worth the price of admission alone.)

Win It All may have a very familiar-sounding story, but Swanberg’s artistry lies entirely in the details and execution. Shot on 16mm, the movie has a warm ’70’s vibe evoking, among other films, Robert Altman’s classic California Split. Eon Mora’s beautifully burnished cinematography retains its celluloid-like texture even through viewing on the small screen.

Swanberg also excels in capturing the multicultural flavors and textures of modern American cities. Eddie interacts with many characters who, even in the brief time some of them appear, convey full lives and come across as much more than simply background or peripheral characters. The bar scenes are just many artfully staged examples of how Swanberg revels in the beauty of humanity and camaraderie.

Win It All is also a very funny film, Swanberg’s funniest yet. The humor is greatly enhanced by the way Swanberg and Johnson bring out each other’s best qualities. Swanberg’s visual acuity and sharp character insights lend deeper shadings to the impulsive and immature roles Johnson often plays, while Johnson’s expert comic timing and charismatic, sympathetic presence proves the ideal canvas upon which Swanberg can successfully bid for mainstream appeal without compromising the qualities that have made him such a valuable, important filmmaker.

Thanks to Netflix, Win It All will be Swanberg’s most widely distributed—and hopefully viewed—work to date. If the larger profile this potentially affords Swanberg helps him become a much more recognized name among the general public, it would hardly have happened to a more deserving director.

Directed by Joe Swanberg
Written by Swanberg, Jake Johnson.
Released by Netflix
USA. 90 min. Not rated
With Jake Johnson, Aislinn Derbez, Joe Lo Truglio, Keegan-Michael Key, and Jose Antonio Garcia