Jake Johnson and director Joe Swanberg have become a Chicago film power duo. As fellow Chicagoans (well, ahem, technically they’re both from the suburbs), their collaborations are uniquely in tune with the city’s feel and aesthetic—Johnson and Swanberg’s characters feel almost too familiar to Chicagoans. Their latest movie, Win It All (now streaming on Netflix) is no exception. The story follows Eddie (Johnson), a gambling addict trying his best to get his life together, and like Easy and Drinking Buddies was filmed all over Chicago. We caught up with Win It All star Jake Johnson to chat about hometown pride, shooting on location and creating a half-written-half-improvised film.
Photograph: Courtesy Netflix
So you’re from here, right?
Yeah, I grew up in Winnetka then when I was 15 I moved to Evanston.
You, of course, have a history of working with Joe Swanberg and shooting these movies in Chicago. Why is it—apart from hometown pride—that you want to keep coming back and setting your stories here?
I just find it to be a very interesting city. I find the people to be the kind of people I can really relate to. I also think, as a city, it’s my definition of what a city’s supposed to look like. I love the buildings and the diners and the dive bars and the lake. It’s hard for me to want to create something that isn’t based here. This is where it all started for me.
And you’re based in L.A. now right?
Yeah, my wife is L.A. and the kids go to school there, so everything’s L.A.
Well, I’m glad you keep coming back here to shoot films.
My connection here will always be the movies I do with Joe.
So I watched Win It All, and I loved it. Something that’s so satisfying about watching the movies you make with Swanberg is how as a Chicagoan, I’m like, “Oh! I know where that place is, I know where that place is…” There’s a really distinct feel, a very purposeful portrait that’s being drawn of Chicago. When you’re writing, do you just write “diner” and “movie theater” as the settings, or do you have specific Chicago locations written into the script?
It’s a combination of both. In this one, we were thinking about specific diners. Joe’s a big part of that, too. We discuss different kind of places—we decide on a type of place or a type of feeling, and then we see who’s available.
Am I right in feeling like Win It All is more of a standard, three-act story than say, Drinking Buddies?
It is. So, Joe has always done more of a free-flow style—like the show, Easy—he likes to write collaboratively, and while on set. We’d done that on Digging For Fire, but I wanted to experiment a bit. I went to NYU for screenwriting, so screenwriting’s a big thing for me. I really like the three-act structure. For Win It All, we wanted to see if we could do a three-act story in a Swanberg-style movie. We kind of combined the roles, and I loved the way it turned out.
What makes it “Swanberg-style” if you’re taking away that free form?
What I think makes Joe’s movies so great is how he gets such naturalistic performances, the way that his movies feel, the way that his characters are authentic and believable. It just feels like a slice of life.
Tell me about the balance between the script and improvising. I know that Drinking Buddies was mostly improvised, but…
We had a solid script, but we don’t care too much about dialogue. No one was allowed to improvise a story beat that didn’t work. We knew what had to happen, and we had a version of the script, but we let the actors slightly change the wording. For example, in the scene where my character pulls up, and Joe Lo Truglia does that whole set-up about like, “Come on in, blah blah blah.” That was a bit that we wanted to do, but the specific things that Joe said were up to him. We just told him to make fun of my parking, make fun of my clothes, talk about how great your places is, show that you have a sense of humor. But what he specifically says—Joe Lo Truglia’s take is going to be funnier than anybody else’s, he’s hilarious. So we’re happy to give Joe that thought before we start shooting, and see what we comes up with, because then my reaction is authentic, since I’ve never heard Joe say that specific thing. So, it’s been written, but it’s improvised too.
Photograph: Courtesy Netflix
I really love the scenes between your character and Keegan-Michael Key’s, where he’s calling you out on your bullshit. For the viewer, that’s really satisfying to watch. Key is an awesome improviser, so how’d those scenes work out when you were shooting them?
He was so funny, so talented. Keegan would practice by reading the scene that was written, block it as it was written, then once we were shooting we would keep going and keep expanding on it. So a lot of what Keegan does is improvised, so the beats are written out, but he’s making his own jokes.
Was there more scripted dialogue in Win It All than there was in Digging For Fire and Drinking Buddies?
It’s not even close. Digging For Fire had like, a fifteen page treatment, and Win It All had a full screenplay. We did development on this, got notes from our agent on it. We knew everything we were supposed to do. In Digging For Fire, we would show up and kind of know what needs to happen, but not specifically.
I love how much of it was shot on the Red Line—down in Chinatown?
Yeah, the scenes where I’m gambling were down in Chinatown. But we shot all over the city.
That first scene where you met Eva and her friends, where was that bar?
One second, I’m actually with Nicky Excitement, let me ask him. [to Nicky Excitement off-phone] Hey, where was that bar where we shot the scene where I met Eva? O’Lanagan’s? [to me] O’Lanagan’s bar. Oh, it’s shut down? Well, now it’s shut down.
Oh, well, now it’s preserved forever. I was just trying to place that scene—it’s part of the fun of watching your movies. Tell me a little bit about working with Aislinn Derbez, she was wonderful.
She’s wonderful. This is her first English-speaking movie.
Really?
Yeah, she’s a movie star in Mexico.
That’s amazing.
We really wanted her and really liked her, but English is a second language. So, we didn’t realize how goofy Aislinn was. And I mean that as a compliment—she’s just a fun, silly person. And so our Eva character didn’t have that in the script, that’s something she brought to the character, which really helped with our love story.
If this was her first English-speaking role, was she still doing the same amount of improvising, or were your scenes with her more scripted?
She did more improv than anybody else. We didn’t want her to get stuck memorizing English words, even though she can. We’d just say, “This is the point of this scene,” and let her kind of improvise and act around it.
Okay, one last question—favorite spots in Chicago?
I’ve always loved Old Town Ale House a lot. Also the Diner Grill, that was a diner I went to growing up. That’s what jumps out.
Catch Jake Johnson and Joe Swanberg host a screening and Q&A at the Music Box Theatre on at 7pm on Saturday, April 8. Win It All is now streaming on Netflix.
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