Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
The films of Joe Swanberg have a very distinct visual and tonal aesthetic. Drinking Buddies, Happy Christmas, and Digging For Fire are all simple, character-driven stories steeped in authenticity, improvisational dialogue, and early-adult “what does it all mean?” malaise. With razor-sharp focus these movies eschew shiny cinematic bells and whistles and instead linger in the small, genuine moments life has to offer. Premiering today on Netflix, Win It All, which Swanberg co-wrote with frequent collaborator Jake Johnson, doesn’t deviate from that tried-and-true formula, but the gambling comedy does double down on the narrative, resulting in Swanberg’s most complete film to date.
Win It All stars the aforementioned Johnson as Eddie Garrett, a man whose gambling addiction leaves him vocationally and emotionally listless as he circles the drain of insolvency. Eddie’s life is best summarized by his sponsor, portrayed by the always brilliant Keegan-Michael Key.
“You’re a loser. You’ve never won. You lose, lose, lose. USDA prime rib f*ckin’ loser.”
But as any gambler knows, it only takes one lucky card to get back in the good graces of Lady Luck. Things begin to improve for Eddie after an unsavory acquaintance offers him $10,000 to look after a mysterious duffel bag while he’s in prison. So, what’s in the bag? “Don’t worry about it,” says the soon-to-be incarcerated man!
Funny thing about gamblers: impulse control is rarely found on their list of special skills.
The allure of the unknown is too much for Eddie to handle, so he opens the bag to find an assortment of items that would definitely be found on a murder’s shopping list, but more importantly, copious amounts of cash. Unfamiliar with the “know when to hold ’em/know when to fold ’em” philosophy, Eddie gambles away a large portion of the fortune he was supposed to be protecting. As you can imagine, losing the cash of a man who owns his very own bag o’ murder is not exactly ideal. When his buddy’s prison release is shortened, Eddie suddenly has a small window of time to win back the money or face certain doom.
This might not seem like a traditional Swanberg movie, but Win It All deftly balances the gambling plot with Eddie’s personal journey from extended adolescence to adulthood. The film doesn’t romanticize the life of a gambler. Eddie’s not suave. He’s not money (and he knows it). He’s hanging on by a thread. The film is a breath of fresh air because it zigs where so many films that deal with gambling tend to zag.
The gambling genre has a tendency to eulogize the protagonist’s helter-skelter life of debauchery. Paul Newman confidently decreeing he’s back? Matt Damon’s Mike McDermott heading to Vegas with three stacks of high society? There’s an allure to those characters; a pang of regret that we’ll never hop a train to Anytown, USA and experience the unpredictable life of a gambler. Sure, Eddie’s likable, but that’s more due to the inherent affability of Jake Johnson than anything remotely resembling envy for his lifestyle. Johnson’s a reservoir of charm. He could portray a serial killer, and I’d be like, “I don’t know? Maybe those 38 people just had it coming?”
Despite his gambling affliction, Eddie begins to turn his life around. He takes a normal job with his brother (the incredible Joe Lo Truglio, who goes against type by playing the rational straight man) and embarks on a romantic relationship with Aislinn Derbez’s Eva (who previously appeared in Swanberg’s Netflix series Easy). Despite his initial antipathy about the prospect of living a “normal life,” Eddie begins to appreciate the cozy charms of ordinary.
“I gotta say, I like having a job. I like working my way up in that company,” Eddie admits. “I like having a girlfriend. I like feeling like an adult and not like a degenerate.”
Many films of the genre depict a “normal life” as an undesirable slog barely tolerated by squares who can’t handle the volatility of chance. But in Win It All, the stability of settling down is viewed through an aspirational prism. The life of family dinners, 9 to 5 jobs, and bowling nights isn’t a penalty one must endure after suffering a bad beat; it’s the pot of gold at the end of the rainbow.
A couple of years ago, the second act of Win It All would have been the entire story of the film. A man tries to kick a debilitating addiction while he gamely pursues a new, uncertain future. But Swanberg and Johnson have evolved as storytellers. They crafted a fully developed, engaging narrative without losing the essence of what makes their films so damn compelling. For fans of Joe Swanberg and Jake Johnson, Win It All is a sure thing, but even if you’re unfamiliar with their previous films, this entertaining Netflix movie is worth a roll of the dice.
