Joe Swanberg is an indie filmmaker in a renaissance period. Yes, he helped create mumblecore with filmmakers like Mark Duplass, Andrew Bujalski, Lynn Shelton and Aaron Katz, but Swanberg has arguably veered the least away from his improvised roots. In fact, unlike say, The Duplass Brothers, who (largely) tightly scripted their excellent HBO show, “Togetherness,” Swanberg has mostly kept his loose methodology. It seems like a gamble, especially with name actors in the mix who likely don’t want to waste their time or fall flat on their face, but Swanberg understands how to hone that alchemy of spontaneity and character traits and spin them into something organic and life-like. That is all to say, that methodology is changing…slightly.

READ MORE: Joe Swanberg Gambles On A Lovable Loser’s Redemption With ‘Win It All’ Starring Jake Johnson [SXSW Review]

Swanberg’s been on a roll ever since 2013’s “Drinking Buddies,” his sort-of-“mainstream” breakthrough starring Olivia Wilde and “New Girl” star Jake Johnson. And while the film has opened many doors to the director, including far-reaching access to more stars and relatively bigger budgets, perhaps the biggest boon yielded from the film is his fruitful collaboration with Johnson. The director and actor co-wrote 2014’s Paul Mazursky-influenced relationship dramedy “Digging For Fire,” and for their third collaboration, “Win It All,” the pair decided to explore the world of gambling, addiction, and winners and losers (read our SXSW review here).


And while “Win It All” still features Swanberg’s patented loose and organic style, the drama is actually his first scripted film, something the filmmaker said he tried in order to challenge himself and do something a little different. Centering on an inveterate gambler (Johnson) who can’t catch a break, his life is changed twofold: when a lovely lady enters his life and shines a glimpse of a promising future, and when a duffle bag full of cash from a friend going to prison enables all his worst tendencies.

Co-starring Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key, the film then charts the path of an addict trying to manage his compulsions while keeping the hope of a blossoming relationship alive. We recently caught up with Swanberg over the phone to discuss “Win It All,” which debuts on Netflix today.

Let’s start at the beginning. What was the genesis of “Win It All”?
Well, Jake Johnson and I had worked on two films before, and the early genesis just came out of the desire…to collaborate on another project. Typically, we kick around a few ideas around before we land on something that we’re both excited about. So, we started with the idea of a duffle bag and an acquaintance headed to prison and asked ourselves if that was interesting or not. Then we started to craft the character and figure out who this guy was and what the temptations were. So, over a couple months of we batted ideas around — we don’t live in the same city, so our collaboration begins with emails and phone calls.

With “Win It All,” though, we decided we would write a script this time out. So when we started to feel good about the idea, we started doing in-person writing sessions, but that was basically anytime I was in L.A. for business. So it ended up being a project we did in our spare time. He’s on “New Girl,” so the windows of time where he can work on projects are pretty narrow, and so that often dictates the timeline.


Oh, so you used a script this time, wow.
Yeah, it’s the first time — it’s the most I’ve ever written for a film. We still improvised the dialogue and there’s still a lot of the process that was the same as our other collaborations, but going in, we had something like an 80-page, fully formed script. For the both of us, having done two heavily improvised films, we were interested in the challenge of trying to write something and attack it from another angle, a more conventional standpoint.

So, let’s get to it. Who’s got the gambling problem?
[Laughs] I definitely have the independent film gambling habit. I relate to the character a lot because I’m often putting my own money into my own movies. So, it usually feels like a pretty intense form of gambling each time out. While we were shooting “Drinking Buddies,” Jake told us all a story about how he used to work in the casinos in California when he first moved out there because that way that system works, someone plays as the house, so Jake was like a professional card player for a couple years at the start of his [stint in] L.A. So, we took some of those stories and modeled it on people we knew and ourselves and that character came out of that process.


So, no one’s into AA for gambling issues then.
[Laughs] Not yet!

So you and Jake have done three projects now. What is it about your chemistries that make you keep coming back for more?
I think it’s a level of trust and a mutual desire to learn from each other. We complement each other really well and in terms of our experience, we came from really different backgrounds. Jake was much more of a writer before he became a performer, and with his work on “New Girl” and bigger Hollywood projects, he’s bringing a really different perspective, and with my producing experience and making small movies myself, I think he’s really interested in [that] side of independent filmmaking. Plus, we always have a really good time. Personally, as a director, I think he’s an amazing actor and I’m always excited to push him to play characters I’ve never seen him do before. He’s made me laugh as hard as anyone has ever made [me laugh] before, and so the set is really [a] fun and easy environment when I’m working with him. It’s a great relationship, we fall in line around the same projects, and we both want to push each other and try new things.

I assume the collaboration will continue then?
For sure. I couldn’t say when, but it definitely will. I can feel like we’re in the realm of kicking around ideas and making another movie together. Sometimes it comes together quickly and sometimes it doesn’t, with other projects in between, but I think it’s very safe to assume another movie will happen in the next year or two.

win-it-allUnlike “Drinking Buddies” or “Digging For Fire,” there aren’t many stars in the movie. Was that a conscious choice? Also, you’ve got Arthur Agee from “Hoop Dreams.”
I acted with Arthur in a short film, so I’ve known him for a few years and I was always impressed with his acting. So, I cast him and he jumped in. He totally got the improv and he’s easy to work with, and adds a nice vibe to Jake’s friends in the movie. And “Hoop Dreams” was a really important film to me, and it’s really interesting to know him as an adult now because the whole world knows so much about his high-school experience, and with a lot of subjects of famous documentaries, they sometimes don’t remain relevant to those outside the scope of when the filmmakers chose to follow them, but it’s nice to know Arthur as a real person. He’s still in Chicago, he’s still the same guy, but with real adult responsibilities like all of us. I just enjoy working with him, and hopefully he’ll be able to get into more projects.

The rest of the cast, we just wanted to cast who was right for the movie regardless of who they were. And so we have Joe Lo Truglio and Keegan-Michael Key, but you know Aislinn Derbez [Jake’s love interest in the movie] is a huge star in Mexico. We considered other names, but we wanted a fresh face, but the benefit was someone who can truly act.

win-it-all-jake-johnson-5DM34606_RSo, I have to ask about your show “Easy,” and working with Netflix on a television series, both of which are new for you. What were those experiences like?
I loved it, honestly. I got to keep my favorite aspects of filmmaking and then I get to learn a lot more — working in a 25-minute format is really different than feature-film work. So, it was like developing a new way to tell stories, but also like short films. Like that open-ended structure and quality to short films where there’s no expectation to wrap things up nicely. And that’s the kind of exploration of what I did with my earlier films, more open and focusing on character. It’s an amazing project for me and I really love it. I hope to do it for a very long time, and it’s something that allows a level of familiar exploration, but there’s more money and infrastructure and support system in place at Netflix that allows me to be trying to new things. So, it’s a nice combination of feeling like I can play, but after 12-13 years of indies, a platform where the playfulness can find an audience.

I’m about to start season two, we’ll start shooting pretty soon, we’ll shoot another eight episodes and I’m really hoping that in between film projects, “Easy” is a thing I can keep returning to and following these characters over time. That’s another exciting aspect of nearly following these characters in real time in a way that movies never really allow.

Oh, so you’re using the same actors and characters, then?
Some of them, yeah. It’ll be half and half, reconnecting with these characters a year later and then continuing to introduce new characters and storylines.

“Win It All” is available to watch on Netflix now.