I will watch any movie about gambling…especially degenerate gambling. Win It All is not exactly a poker movie, although there's a couple of poker scenes. Win It All is more of a degen gambling film because the main character is a former member of Gamblers Anonymous, who parks cars at Chicago Cubs games by day, then stays up all night gambling. Our super degen plays poker and blackjack at illegal gambling parlors in Chinatown. At one point, the super degen is pitching cards into a mixing bowl in the back of a Chinese restaurant. Then, our anti-hero is bitching that a monstrous rainstorm cancelled races at the horse track. When he got super stuck, he weaseled himself into an exclusive high-stakes poker game in the Chicago suburbs.
Yeah, someone made a movie about someone who will gamble on anything.
Indie filmmaker Joe Swanberg (Drinking Buddies) typically outlines his films then allows his actors to improvise from scene to scene. For Win It All, Swanberg and his co-writer Jake Johnson, took a different approach and penned a script. The departure with an actual screenplay was a shift from his collection of low-fi mumblecore flicks. As a result, Win It All is one of Swanberg's most cohesive and best films to date.
Although Swanberg admitted that he's not a poker player, he understood the gambling aspect as an indie filmmaker and producer. Swanberg self-financed his previous films to guarantee creative control. He constantly gambled on his own projects with his own money and whatever money he borrowed from friends and family.
Jake Johnson, on the other hand, is an avid card player and made sure the poker scenes were authentic. When Johnson moved from Chicago to California to pursue a career in acting, he played low-stakes poker and blackjack on the side to supplement his income. Johnson found it easy writing for the character of Eddie because he played against a similar personality… a likable loser and know-it-all that can't ever catch a break. Keegan-Michael Key plays Eddie's GA sponsor and he summed up Eddie's personality the best: "You're a loser. You lose, lose, lose."
Win It All tells the story about Eddie (Jake Johnson), a degen gambler from Chicago, who stops attending Gamblers Anonymous meetings. Eddie bounces around from odd job to odd job to make a quick cash… so he can gamble it up. He can't even afford to buy a cup of coffee in the morning after staying up all night gambling in dark and smoky gambling dens in Chinatown. Eddie gets a visit from a nefarious friend who is about to serve a six-month jail sentence. He gives Eddie a bag and tells him to watch it for him until he gets out of prison…if everything is still inside then Eddie will get $10,000. Eddie has instructions not to look in the bag, but of course, Eddie looks in the bag and discovers bricks of cash. What would any degen do? Peel off a few bills and gamble it up! Eddie goes on a run… before he loses it all and then some. The total destruction…. Down $21K! Reality sinks in and Eddie decides to quit gambling and find a square job to pay back his friend…otherwise suffer violent consequences. Eddie returns to Gamblers Anonymous and takes an entry-level job in the family landscaping business. Eddie also meets someone at the neighborhood bar… a nurse named Eva (played by Mexican actress Aislinn Derbez). Eddie ends his evil gambling ways to focus on normal things like a job, relationship, and slowly paying back his debt. Just when it seems like Eddie is back on track, his friend from prison calls with good/bad news… he is getting released from jail several months early. Eddie has one week to figure out how to recoup five figures in losses. What would a degen do if they were stuck bigtime? That's right… gamble it up!
I won't give you any spoilers on what happens, but Win It All defies the trope of the downtrodden gambler who meets a girl who helps pull him out of a tailspin, turns luck around... and they live happily ever after.
Joe Swanberg, Director of "Win It All"
I am a gambler in life. I am not a card player. I gamble on movies.
Hollywood took a shot and whiffed with the remake of The Gambler (with Marky Mark a.k.a. Mark Wahlberg reprising the role of James Caan). Hollywood also shit the bed with Runner Runner, the Ben Affleck online poker vehicle penned by Rounders writers Brian Koppelman and David Levien. After two big misses, you would expect major studios to steer far away from gambling/poker films.
Thank God for Netflix and indie filmmaking! Otherwise, we wouldn't have special films like Mississippi Grind and Win It All.
Mississippi Grind was a small-budget indie film that surprised me (you can read the review here), which explored the bittersweet off-the-felt antics of degen card players – played by Ryan Reynolds and Ben Mendelsohn – who were both sort of losers in life constantly seeking that next big score.
Win It All fits into the gambling genre, but it's definitely not a poker film despite the plot having a heavy poker element to it. As a stand-alone film without knowing anything about Joe Swanberg and his style of filmmaking, Win It All works as because of the likability of Jake Johnson's Eddie character.
Everyone knows an Eddie. We've all played poker with an Eddie. Some of our friends are Eddie. It seems like there's a guy like that in every poker room in Chicago… in America… in the world. Doesn't matter if it's Monte Carlo, or Las Vegas, or a private game in a dingy alley in Chinatown… there's a guy like Eddie gambling away his last $200 with hopes of going on an epic heater. Someone made a movie about one of my friends…and Jake Johnson's portrayal of Eddie felt bone-chillingly realistic.
Win It All is currently available to stream on Netflix. Watch the trailer here…