Comfort Zones and Clichés: Jake Johnson Discusses Win It All and Playing a Gambler

“Write what you know” is familiar advice for anyone looking to tell a story, and it seems to suit Jake Johnson and Joe Swanberg just fine. Collaborating for the second time as writers, and third time as actor and director, the duo returns to their hometown of Chicago in Win It All, in which Johnson plays Eddie Garrett, a poker addict that falls into protecting a bag of money for an acquaintance in jail. This turns out to be a challenging task. Eddie loses portions of it at underground poker clubs and enlists the aid of his mentor (Keegan-Michael Key), his brother (Joe Lo Truglio), and later his girlfriend (Aislinn Derbez), to help him out of debt and reclaim his life.

What might have been a precarious proposition for most actors—playing a diseased gambler—was less frightening than exciting for Johnson, who wanted to explore the type of troubled character he has met, in various circumstances, throughout his life. That familiarity proves helpful, as the movie resists the clichés of its genre and finds something authentic in its portrayal of a lovable loser. After working together on Drinking Buddies and Digging for Fire, Johnson and Swanberg make sure to give this potentially dark subject matter warmth and comedic texture, affirming their strong creative chemistry. We spoke with Johnson about the film, which debuts on Netflix this Friday, his love for Chicago, working with Netflix and the potential end of New Girl.

Paste: I know you’re a big Cubs fan. How exciting is it to start the season calling your team the defending World Series champions?
Jake Johnson: It’s a really nice feeling. I spent so many years of my life having the same arguments with opposing fan bases where they always got to win the trash talk by saying “1908.” So being able to say “2016” is a nice feeling.

Paste: Being from the Chicago area, how much fun is it for you to make another movie there?
Johnson: Well, it’s a big priority for me. Part of my relationship with Joe Swanberg is we like making Chicago movies. We experimented with it with Digging for Fire, which we shot in L.A., and it feels more comfortable for both of us at this point to make Chicago movies with Chicago characters with a Chicago crew. Chicago was a huge part of my life growing up, and I’ll always have a lot of love for it, so it’s really nice to make films about it.

Paste: What does being more comfortable in your home city allow you to do as a writer and actor?
Johnson: It allows me to write characters that I feel. The character of Eddie in this movie was loosely based off of a feeling that I got from my uncles when I was growing up, and from different Chicago characters. It’s not a character that is foreign to me. We’re not writing a story about a kid who grew up in rural Japan, where, [you have to] figure out what it means to grow up there. I don’t have to invent a lot because I know Chicago. I know the people—I was the people for a lot of my years before I moved out. I experienced it every day. So, it’s a comforting feeling going back and shooting in Chicago.

Paste: What made you want to play Eddie Garrett, especially because he’s a character that can be tough to embrace?
Johnson: I feel as though a lot of those gambler-type characters are played in a very similar way most of the time, where they’re Joe Cool, but a screw-up. I know more of those fringe-gambler people, and the truth is, with people with addictions, there’s often a real sweetness to them, a real vulnerability. The problem with people who are really addicted to something is that for many of them you feel really sad for them—you might even like them. You just hate what they’re doing. I wanted to play Eddie in a way where he wasn’t your same-old cool cat gambler—the coolest cat in the coolest club. I don’t have much interest in those characters, so I wanted to make Eddie a character who I could relate to and who just finds himself in a situation that was greater than his ability get out of.

Paste: Did you have any experience at an underground poker club?
Johnson: I have. I love playing cards. I’m definitely way more PG than Eddie Garrett is, but when I was shooting Let’s Be Cops, I got to talking with a member of the crew who was a poker player, and he told me he knew of a game. I thought it was a home game—a bunch of guys playing low stakes—and we ended up going into the ’hood in Atlanta and going behind a Subway restaurant to this weird room. [There was] a guy who was a guard there and had a hand gun and a generic jacket that said security, and we played this weird version of Omaha with wild cards for high stakes. It was with gangsters, and it was intimidating and a lot of fun and definitely high stakes and a higher intensity than I was comfortable with. I played and I left, but I thought, ‘What kind of character lives in that world and loves it?’ And so Eddie was a character who goes to those places, loves those worlds and gets locked into it.

Paste: Between you and Joe, how much did you draw on your own experience and how much did you take inspiration from other classic gambling movies?
Johnson: Well it was interesting because Joe was not a poker guy, so in terms of making this movie, he didn’t care about it. He was our gauge because I love poker; I could watch those poker shows all night. But as for the actual game of poker, Joe was like, “I have no interest in making a movie about it.” So if you notice, what the hands are, and how people are playing hands, means way less in this movie because Joe wanted to make a movie where you don’t have to like or care about poker to like this movie. You’re just watching a guy’s journey, so it was an interesting mix.

Paste: What was different about working with Joe this time around compared to your last collaboration Digging for Fire?
Johnson: A lot. For example, Digging for Fire, we just had a treatment for the actors to not only improvise their dialogue, but suggest story beats and move the story and be part of the collaboration. On this one, we had a script, and we knew exactly what we needed from the stories in terms of what the actors brought to the table. They were allowed to improvise and change their dialogue, but the intentions had to stay the same because every scene leads to a next scene. So Digging for Fire was a great learning experience for me. It taught me that I like to have more control over the story, and I like telling a very specific story, but when you’ve got guys like Keegan-Michael Key or Joe Lo Truglio, you don’t need to tell those guys how to say a joke. They know exactly how to get words out of their mouth.

Paste: What’s the difference for you as an actor when you’re writing your own character and material versus just seeing a new script and trying to find your way into one from somebody else’s perspective?

Johnson: It depends. One of the reasons I don’t say yes to a lot of projects as an actor is I don’t need to stay totally busy, because if I see a script and I don’t get it, and I don’t understand the intention, I don’t need to spend months of my life trying to find out what a writer meant by something. If it doesn’t feel familiar to me, if it doesn’t feel like something I care about, then it’s not a story worth telling for me. One of the nice things about writing is I understand all the reasons that the character would do things and why they would do it, so I don’t need anybody to explain to me why a character would be in a situation. It makes it easier for me to try and convince an audience why a character’s doing it. As an actor, sometimes I’m given scenes of material that I don’t think are truthful—I don’t think this character would do it. [But sometimes] it’s your role as an actor to just shut your mouth and do it, even if you don’t believe in it. I get that, but it’s not something I need to always do.

Paste: It was also refreshing to see that when Eddie gets a job from his brother, he doesn’t relapse and actually enjoys the daily habits of work, which is rare to see in movies regarding these kinds of addictions.
Johnson: I actually think there’s a lot of truth to that. If you have any addicts in your life, when they quit drinking and start working out more, or do whatever they do, there’s a lot of happiness in that for them.

Paste: Did you speak to any gambling addicts to tap into their psyche a bit more?
Johnson: As one of my first jobs when I first moved to L.A, I worked at the Hollywood Park Casino, down in Inglewood. And so I spent 40 hours a week hanging with degenerate gamblers for the first year that I was out in L.A. I had hours and hours of conversations, and that was where the realization was that a lot of these gamblers aren’t gambling to win, they’re actually gambling to lose so that they can feel like a loser, because that’s the feeling they were craving. That was the thing that really blew me away. And at the core of this story, that was one of the things I wanted to [convey]. I think people associate gambling with the cool gambling movie, that what you’re chasing is the Rat Pack style—flipping the coins up in the air and driving the convertibles. But real gamblers are chasing a darker, more depressing feeling, that loss of control when you’re out of money because you lost. But I also didn’t want to make a movie that’s just depressing and heavy. I like to make entertaining movies. In my core I believe filmmaking is escapism, entertainment. If someone is going to give me an hour and a half of their life, if they’re going to take a break from their jobs, their families or friends, I don’t want to just bum them out. I want them to have an hour and a half where there could be a real story about something, but there are also a lot of laughs.

Paste: That’s where Keegan-Michael Key and Joe Lo Truglio come in. How easy is it to find a rapport? Do you just jump right into it with them?
Johnson: There’s a thing I’ve learned about professional actors. There are certain actors who can jump onto a project and see the tone almost immediately and figure out their way into it. Lo Truglio and Keegan are the definition of professional actors. They understand what they’re doing, they know how to come in. It took one conversation with Keegan for him to realize that he’s the guy who comes in, he’s the sponsor, he’s serious, but if we don’t have laughs there, then people hate him, and people hate those moments with this character. He reads the script, he gets it and he goes, “I’ve got an idea—let’s start shooting,” and before you know it we’re shooting stuff and he’s improvising. That’s the stuff that makes it in.

Paste: What was it like working with Netflix on this, and is it hard knowing the audience won’t get to see this in a theater with other people?
Johnson: Well, Netflix was our first choice on this movie, because when we did our movie Drinking Buddies, we really wanted people to experience it in the theaters. Nobody went out to the theaters. So, people found that movie and continue to find that movie from streaming sites. So I’ve been trying and beating the drum for people to go out and see these indies, and a lot of times the reaction I’ll get from social media and people talking to me is they’ll find movies on their own time. So this as a theory was, “What if we made a movie that was big and had big laughs?” You saw at SXSW, laughs that could fill a theater, you could all laugh together.

Paste: Yeah, the most raucous times were when the graphics of Eddie’s debt showed up on screen.
Johnson: And it gives a really fun rhythm in the crowd, but I’m a real believer—and I say it because it’s how I watch most of my stuff, I don’t go to the theater that much—that you can still have that experience alone or with somebody else watching it at home, and we want people to find this movie on their own. We want them to discover it when they discover it.

Paste: Since New Girl Season 6 just ended, what was your experience like with the show and is there a chance for another season?
Johnson: It’s not officially over. It might be coming back. We don’t know. But if it ends, it will be a really sad end to a great era. It’s been a hell of a show. It’s been an incredible life experience. If we come back, then we’ll roll up our sleeves and get dirty.