Win It All is mumblecore pioneer Joe Swanberg's 18th feature film since making his debut with Kissing on the Mouth in 2005. So, we should all know what to expect from one of his movies by now: practically non-existent budget. No script; just an outline for what is often a semi-autobiographical story. Almost exclusively white actors improvising all of the dialogue, and usually playing someone connected to the entertainment industry (like an actress, writer or artist). A worldview concerned only with Los Angeles, New York, and, on occasion, Chicago. And scene after scene of people simply talking to each other. Really, you don't watch a Joe Swanberg movie for the plot; you watch for the conversations, which rise or fall based on the improv talents of the involved actors.
Thus, with Win It All it's likely as simple as this: if you like Swanberg movies you'll probably like this one; if you don't you won't.
However, that's not entirely true because New Girl/ Jurassic World star Jake Johnson is just as much responsible for this movie as Swanberg. Johnson co-starred in Swanberg's Drinking Buddies (2013) and then co-wrote and starred in Swanberg's Digging for Fire (2015). He is again the co-writer and star of Win It All, playing a gambling addict attempting to regain control of his life after bottoming out in epic fashion when some idiot entrusts him with looking over a bag of money for 6-9 months and somehow didn't realize he would just gamble it all away.
Through these collaborations with Johnson, Swanberg has been forced to branch out. He's no longer stuck entirely up his own ass making movies about people who make movies (or art) for a living. That's his jam, but not necessarily Johnson's, who based both Digging for Fire and Win It All on his own life. Thus, Swanberg has now shifted focus to more blue collar-like characters, such as the brewery workers (Johnson and Olivia Wilde) of Drinking Buddies and gym teacher and yoga instructor (Johnson and Rosemarie DeWitt) of Digging for Fire. Win It All continues the trend by focusing on a man who works odd jobs in Chicago, such as parking cars at Cubs games, for a living, and has an older brother (Joe Lo Truglio) who owns a lawn care company.
Moreover, Win It All is also Swanberg reaching out to include a more diverse cast. Thus, Keegan-Michael Key plays Johnson's sponsor, and Mexican actress Aislinn Derbez plays the love interest. The guy who actually kicks off the plot (Jose Antonio Garcia) is also Hispanic. So, um, kudos.
Does all of that add up to a better-than-average Swanberg move, though?
Again, the answer depends on your mileage with Swanberg and Johnson. Some on Letterboxd have described Win It All as "barely a movie" whereas others regard it as easily the most scripted and best work Swanberg has ever done.
For me, the highlights were the funny, but insightful scenes between Johnson and Keegan-Michael Key, and the surprisingly tense card game in the finale, which recalled any number of prior gambling movies in execution (I was personally reminded of Rounders and Mississippi Grind) and suggested an actual growth in Swanberg's talents behind the camera. However, the central message of the film seems muddled (gambling is bad unless you win?), and while it admirably touches on some uncomfortable truths about addiction and the rough road to recovery it also keeps telling that same story over and over again. By the three-quarter mark I didn't know if I could take another scene of these characters saying roughly the same thing yet again.
THE BOTTOM LINEIs there enough here to make this a film I'd recommend? Not really, not unless you are already a fan of Jake Johnson or Joe Swanberg or both.
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