Directed by Joe Swanberg
Joe Swanberg’s most well-known film might be 2013’s Drinking Buddies. It’s a film that focuses on the platonic friendship between Olivia Wilde and Jake Johnson. Most of Swanberg’s films, maybe all of them, are pretty quiet and centered on relationships between people. That might seem obvious, but it’s not, at least, I don’t think it is.
Think about a very mainstream action movie. If there’s a love interest, it’s because that’s what’s expected in that type of movie, but if a Swanberg movie has a plot, it usually doesn’t really matter. Instead he focuses on the small moments between people because that’s what fascinates him. A lot of his movies are improvised, though I’m not sure to what degree. Win It All is cowritten by Swanberg and Jake Johnson, the leading actor. They have worked together previously on Drinking Buddies as well as a 2015 film called Digging For Fire.
Just to give another example of what I mean when Swanberg focuses on relationships… Digging For Fire is about a guy, Jake Johnson, who becomes obsessed with the idea that there is a body or some kind of hidden treasure buried in the backyard of the house and his wife are house-sitting. But the story is ultimately about the struggles in Johnson’s marriage with his wife, played by Rosemarie DeWitt. Every movie, to some degree, is really about something under the surface, something which isn’t mentioned in the longline.
Seth Rogen mentioned, in an interview with Pete Holmes on the You Made It Weird podcast, that what a movie claims to be about at the beginning, all but vanishes at the end. As that plot begins to dwindle, the heart of the movie is given more space so that by the end, when the character seems to have lost everything, they’re experiencing a loss of whatever it is that really matters to them.
The longline of Pineapple Express reads, “A process server and his marijuana dealer wind up on the run from hitmen and a corrupt police officer after he witnesses his dealer’s boss murder a competitor while trying to serve papers on him,” but the movie is, at its core, about the friendship between Rogen’s character and Franco’s character, his drug dealer. It’s just a movie about friendship.
I guess what I’m saying, in a long-winded way, is that there is some expectation that movies will unveil some amount of heart, but many of them do it slowly and over time. The “fun and games” portion of a script (aka all the moments you see in a movie trailer) deal more with the plot and the premise than the underlying heart of the film. It often feels like, at least in comedies, the director gets to the point where they sigh and say, ‘I guess now we have to address that the reason this character is acting so wacky is because his father abandoned him when he was 6.’
In a Joe Swanberg movie, though, he seems incredibly eager to dump the plot or any pretense and get to the heart of why a character is the way he is. It’d be like if he directed a James Bond movie, and then by minute 15 there has already been a huge shootout, Bond is injured, and he spends the rest of the movie falling in love with an insurance agent who helps him write his will (because in his line of work he could die at any moment), and he realizes that he’s been flirting with death for way too long and it’s time to settle down.
So, in Win It All, we follow a gambling addict who is given $50,000 to hold onto for a friend while he in prison. The gambling addict gambles using $500 and wins about $1,500. Then he can’t stop himself, so he gambles more of the money and loses $19,000 over the course of one painful night. This all happens in about the first 30 minutes of the film. The “fun and games” portion of the story, which occurs early in act 2 (say, minute 30-45 of a movie), deals with the protagonist getting his life back together rather than him gambling or doing anything about the bag of $30,000 he still has hidden away in his house.
Swanberg cares more about the human side of this, of addiction, of selfishness, etc. The money is almost completely forgotten until the midpoint of the film, when the incarcerated friend says he’s going to be let out four and a half months early.
The protagonist is Eddie (Jake Johnson). He won’t accept his addiction, even though he routinely meets with his sponsor, Gene (Keegan-Michael Key), to whom he usually just announces a crazy plan, hoping Gene will validate his idea. It’s clear that Eddie needs to grow up. His character is further illuminated by the role of his brother Ron (Joe Lo Truglio), who has settled down (wife and a child) and works hard day in and day out at his landscaping company. Ron seeks stability while Eddie lives on the edge, always about to lose it all.
When Eddie finally loses the $19,000 gambling, he turns to his brother and asks to come work for him. If Eddie works for him without conflict for 6 months, Ron will cover the rest of whatever Eddie owes. As this is going on, Eddie meets a nice nurse, Eva (Aislinn Derbez), and we chart the course of their budding romance while he gets his life back together.
At the midpoint of the film, when a story usually digs into the heart of the character, Win It All turns back to the money, which has all but been forgotten for the last 30 or so minutes. It’s almost as if Swanberg through the plot back into the film, realizing he had forgotten about it for a while as he focused on Eddie and his new job as well as the improving relationships between him and his brother as well as his girlfriend.
When Eddie’s friends calls him from jail, saying he’ll be let out in a week, Eddie panics and goes to his brother, asking for more money to cover the amount he owes. Ron, though pleased with Eddie’s progress over 6 weeks, tells him he won’t give in this time. We know that Eddie is an addict, and though he has been improving (even going back to meetings alongside the supportive Gene), we recognize Eddie slipping back into old ways, even if we understand where his urgency comes from.
Ultimately, Eddie has to give in to the gambling impulses he claims he no longer feels, going to a high roller game to try and win the rest of the money back. His plan, should he lose the money, is to skip town, even though that means severing the relationship with Eva and damaging the one with his brother.
The film actually wraps up the plot surprisingly quickly, almost in a single montage. It’s a surprisingly tense, gripping sequence, as we can only tell if Eddie is winning or losing by his reactions, stripped of context. We are never seen the poker game itself, only Eddie’s mannerisms. It’s not until the amount of money he has either won or lost fades in slowly in the lower right hand corner of the screen to tell us how he’s fared that we understand the degree of his success or failure.
So poker never really matters to the film, even if it matters to Eddie. The focus is always on his face and on his improvised lines celebrating victory or wallowing in defeat.
Sometimes a Joe Swanberg film (like those of similar directors Lynn Shelton and the Duplass Brothers), can feel a little too… something. I love improvised films because I feel like you get certain moments and reactions that you might not be able to capture in a conventionally-scripted and blocked out movie or scene. But at the same time, you can occasionally recognize the acting process. There is a fine line between giving us enough details and moments to make the movie feel real and force-feeding us too many of these cutesy moments to make it feel like a student film.
The film is do dependent on Johnson’s performance, particularly in the poker scenes, that sometimes his acting feels very much like acting, like a guy going a little too far. It’s hard for me to explain why, but I suppose it’s just that the informality of the film’s structure starts to feel like it’s been let off the leash.
Still, I really liked this film, and I was surprised by how nervous I was during the gambling and poker-playing scenes, partially because I never knew just how much Johnson was poised to lose at a given moment.
Another touch I really liked in Win It All is when we see Eddie’s dark side come out. Jake Johnson is a charismatic guy, so it’s hard to dislike him, and we don’t, but at the same time he is playing an addict who has pushed the limits of his friendship with Gene and Ron and Ron’s wife Kris (played by Kris Swanberg, Joe’s real life wife). In one scene, at a bowling alley, Ron lets Eddie know that he’s excited for him in his confidence about his new life and his new girlfriend (whom Ron hadn’t met), but Ron tells Eddie to be careful, because Eddie says everyone girlfriend is different than the last. It’s understandable, where Ron comes from, but then Eddie gets pissed, also understandable, and they verge on the edge of a real nasty fight. Ron, however, is always quick to quiet down, wanting to diffuse the bomb before Eddie goes off, and we can guess how it’s probably gone off in the past. I loved this interaction between the brothers, where you understood so clearly how Eddie has to suppress this part of him (both in terms of gambling and living), but also the struggle of Ron to be friends with his brother and to look out for him too, like a parent. This scene, though, is an example too of when the improvisation feels a little too loose, only because the scene lasted a little too long. We got the point well before the moment ended, but we couldn’t cut away until they resolved the conflict.
Win It All is a well-acted, well-directed film that is occasionally funny but surprisingly dramatic and very sincere.