Joe Swanberg’s Win It All is yet another step in the ongoing maturation of a filmmaker previously known as a mumblecore icon. Win It All is a low-key comedic drama that delivers big laughs courtesy of star and co-writer Jake Johnson, who previously worked with Swanberg on Digging for Fire and Drinking Buddies. In their latest collaboration, Johnson plays a directionless gambling addict (hence the wry title) who falls in love with a single mother (played by Aislinn Derbez) and struggles to get his act together. It’s an incredibly familiar formula, sure, but Johnson and Swanberg still manage to make it entertaining, hilarious, and heartfelt.

Sitting at a table across from Johnson and Swanberg, it’s easy to see why they keep working together — their chemistry is effortless and charming, though it comes nowhere close to matching the charisma of Derbez, the Mexican actress (and daughter of superstar Eugenio Derbez) who plays Johnson’s love interest. I was impressed with her performance, which elevates basic material, but I find myself even more impressed when she eventually joins us for the interview. Johnson and Swanberg have this whole history together, and although Derbez is a newcomer — and something of a “wild card,” as Johnson put it — to the Swanberg Cinematic Universe, she feels like she’s been with them all along.

So I’m familiar with Joe through his work, of course, but my only other exposure to you was watching you beat up a friend and former colleague of mine at Fantastic Fest several years ago.

Swanberg: [nodding, laughs] Mm-hmm.

Johnson: Wait, was this that boxing thing?

Yeah!

Johnson: That’s crazy.

Swanberg: [laughs] Well, either I’m sorry or you’re welcome. I’m not sure which.

Listen, it was entertaining, and the debate was fascinating to watch. 

Swanberg: Well, it was for fun. It was meant to be for fun.

Right.

Swanberg: I had more fun than him.

So no boxing matches on the set of this movie? No journalists or directors were harmed during the making of this film?

Swanberg: [laughs] No. Not that I can remember.

But there was some karaoke. Are you all big karaoke people?

Derbez: They are.

Swanberg: I mean, nobody can rival me. I’m the king.

The two of you have been working together for a while, so I’m curious about where this idea originated on that timeline — was it during Digging for Fire or before that?

Swanberg: After.

Johnson: This was in response to Digging for Fire. We knew we wanted to make another movie together, and so Joe had an idea about somebody who ... He wanted to see my character finding a bag and being stuck with that bag, and what would happen there. And then he told me that, and I thought about it for a while, and then I pitched him the story arc without any of the characters really in it, but this could be the three-act structure, and he liked that, then we got together and started pounding it out.

What compelled you to keep developing this story, specifically — because I’m sure the two of you have come up with other ideas. What made this one a priority?

Swanberg: I don’t know. It came together in a different kind of way. I think we were compelled to make something funny after Digging, and I think we built something that felt like a vessel in storytelling structure. To me, the bag thing was born out of a really visual old movie device, and I was just kind of curious whether that would even fit into our world and the kinds of movies we like to make — but also, it wasn’t until we started to get to know Eddie Garrett [Johnson’s character] that I think that structure made sense, or we were compelled to do something specific with it.

Johnson: And I was really interested in doing a Joe Swanberg movie that had a three-act structure to it, and had big story and big stakes to see if we would at least like the movie together — to see how it would feel, and to see if it would work, and then the way we deal with each character, we would have an arc that we would see. But Aislinn improvises how she does her character. We know the beats we need to get to, but then how we get there, we would always have versions. And if you actually see the 85-page script treatment thing, it’s close, but then when she comes in, she’s bringing her own energy. And when Keegan[-Michael Key] comes in, he’s bringing his own energy to it, which made it feel like a Swanberg movie again.

Then you’re like, “Oh, now we’re here and doing it.” Once we’re on set, we know where we have to get, but we also get to have that freedom of a Swanberg movie, so...

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Aislinn, you worked with Joe before, on his Netflix series Easy, right?

Swanberg: Well, we shot this first.

And this is your first English-language film, too?

Derbez: It is.

You’re so charming. I can’t overstate that. 

Derbez: Aww, thank you!

Johnson: She’s not. It’s good acting. [laughs]

Swanberg: The best actor I’ve ever seen.

Okay, fine, so you’re really good at acting. 

Swanberg: Spend 10 minutes with her, and you will know ... but she is very charming in the movie, which makes her scary.

Johnson: She should win an Oscar.

On a very basic level it feels like I’ve seen this movie so many times before…

Swanberg: Mm-hmm.

Swanberg: Totally.

From the outset I was a little skeptical, like, alright movie, I know how this goes…

Johnson: Yep.

But what you guys made is so funny and heartfelt.

Swanberg: You’re right. I’m happy to hear it. Yeah I mean, I think we all feel that way. It’s a pitch where you’re like, “Cool, I get it.” It’s a movie. And what’s fun for me as the challenge, is the movie only works if the stakes feel real, and the movie only works if you don’t know how it’s gonna end or where it’s gonna end or where it’s gonna go. That is a really different kind of challenge than “How do we tell a new story that’s never been on screen before? How do we take an old story that everybody’s seen, and make it fun and exciting again?”

But now that’s the goal for a lot of people, who feel like we only have so many kinds of stories to tell.

Swanberg: Some people would argue we always have enough.

Johnson: If we’re going to get into the story debate ... You know, I came up going to writing school, and the whole thing is there’s only seven or eight stories, and we just recycle them. And then the interesting way to recycle them is, you put the third act first, and everyone’s like, “Whoa, crazy!” Or the way you tell this love story is that you’re like “Well, if you actually break it down into the story structure, they’re all the same stories.” So it seems different because of this device, but if you’re sitting around with it to be cheesy about it, if you’re sitting around a camp story, we all want the same peak of the story — the scary story doesn’t start with, “There was a monster!” [gets quiet] “So, we were all walking around...” No, you’ve got to build to the scary part! There’s just a way to tell a story.

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But the game for Joe and I on this was, well, Joe’s movies do feel fundamentally different. So, what the audience likes, and here’s what we like, is that it’s not that. It’s just connections. It’s just humans interacting. Where can we do that, with a campfire story about [salesman pitch voice] He’s a gambler hard on his luck, somebody drops a bag, he’s got money. Oh, no! He’s at his worst spot and he meets his dream girl. We know that we’re doing the moves, but can the moves work here? That was our experiment. You really need to get lucky and have the right cast, and with Keegan and Joe [Lo Truglio] we were very confident. We knew what that was. We had a wild card [motions to Derbez]. But truly. You know, we said behind your back, “Aislinn was our wild card because the love story is the heart of it.” And if it doesn’t work, then we don’t have something. And the love story was our least fleshed out in terms of dialogue, because we didn’t know who that person was yet.

Derbez: I didn’t have any dialogue. No structure, nothing.

Johnson: And we knew where the beats would have to get.

Derbez: Everybody else knew.

Johnson: But we would say, “All right, so we’ve gotta get here, and then how are we gonna get there?” And we would discuss what we’d want to do, and where we could go, but we also knew if that doesn’t work, if Aislinn doesn’t bring it, we’re in a lot of trouble. And we really didn’t know her. And she really didn’t bring it. [laughs]

It was all editing, then.

Johnson: I mean, no. We used face replacement. With those little balls.

Derbez: Hours and hours and hours.

Those are some really convincing effects.

Johnson: We lost a fortune. We lost a small fortune. But then she came and she was good, and what we didn’t know about Aislinn was that she’s really funny. Truly. And that she was goofy, because the story we’d written with Eddie and Eva wasn’t that goofy. It was actually kind of serious and it was boring — “poorly written,” as she likes to say when you guys aren’t around. But it was just kind of boring. And then when Aislinn came in, we’re like “Oh, it’s fun and it’s goofy, and these people like each other.” And that’s when we were like, “Oh, great!” So that to me is — you get to do the story, but on a Swanberg movie, you don’t find all that chemistry beforehand. That’s where you get to do the work, on set.

Swanberg: And as a director, you have to ask yourself, “How do I make this work when my two leads don’t like each other?” [everyone laughs] And so, it’s a really big challenge.

 

Derbez: I really wanted to say that working with Joe was amazing. It was the funniest set I’ve ever been in. They have multiple personalities all the time, and you never know when they’re true or not. I never knew what was happening. [laughs] And what I like about Joe is that he really trusts everyone, and trusts the real art in every person that he’s with. And that’s really special because he’s not a control freak at all. I’ve never met a director that is not a control freak, and he is so — I don’t know how to say it, but he trusts every person that works with him, and that makes it very special. Then it’s full of heart all the time. He has everything in his mind, but he’s very open to whatever everybody brings, and that makes it very special.

You can see that in the film. Plus you get to work with that ridiculously adorable kid.

Johnson: Refer to me by name. I’m no child. I am 38.

Can I just ask — Jake, how often do people tell you that you look like Jason Mantzoukas?

Johnson: You know, honestly, there is a thing, which is really funny. There are about 10 of us guys of a lot of different ethnic backgrounds, where we all have larger noses, brown eyes, brown hair, olive-ish skin. The amount of people who tell me in my life I look just like their sibling, their boyfriend, or somebody in some movie. Look, I know Jason.

Right, of course.

Johnson: We do not look similar when we are together.

But you do kind of…

Johnson: We have enough of the same stuff that I never realized. There are honestly so many people. Even my wife, we’ll be watching something, and she’ll be like, “Now that one does look like you.” Even my kids, I’ll be watching things online and they’ll go like this [gesturing] “Dad?” No. Brown-haired man, brown eyes, and I’m like, “I know” It’s just the way humans were created.

There’s a movie in there somewhere.

Johnson: The guy who I really have gotten the most, and he and I have talked about it, is David Krumholtz.

Oh yeah, I can totally see that.

Johnson: Because there was an era of time that David Krumholtz and I, when we first met, we literally went like [does double take]. He’s like, “Hey, man.” I’m like, “Hey, man,” and we were both like “F—ing weird, man, we look alike.” We weren’t sure if we were brothers or cousins or whatever. And as we aged, we do look different, but there was a moment in time where I would look at him, and I would be like, “I don’t mind the way we look,” and, “Oh, so that’s how we look in red shirts. Dammit, I gotta get a red shirt. We look good in it.”

Win It All is now streaming on Netflix