I first encountered the movies of David Gordon Green as a college student in Montreal. My friends and I were in film school and Green was our shaman, a kind of mini-Malick whose earliest work—George Washington, Undertow and All The Real Girls—was unusual, poetic and pulsated with youthful energy. It helped that he was a twentysomething film school grad who got together with some friends and just started making their own shit. Some kids came of age wanting be like Mike. We wanted to be like David.

It was only a matter of time until Hollywood came calling. But rather than expand on the emotional lyricism that defined his earlier work, Green decided to do something different. Green decided to make Pineapple Express.

It was a head-scratching move that would go on to define one of the most peculiar Hollywood careers of the last decade. Green has continued to oscillate between genres, from the star-stacked political satire of Our Brand is Crisis, to the twisted comedy of his HBO shows Eastbound and Down and Vice Principals. Next, he’ll try his hand at horror when he directs the latest sequel to Halloween, which he co-wrote with his frequent partner in crime, Danny McBride.

When I encountered Green at the Toronto International Film Festival, it was to discuss the chameleonic director’s latest about face, Stronger, a triumphant biopic about Boston Marathon bombing victim Jeff Bauman, who lost his legs on that fateful day on Boylston street. With the help of a career-best performance from Jake Gyllenhaal, Green has crafted an intimate portrait of a man who, beset by tragedy, became a symbol for the resilience of the human spirit.

Here, Green and I discuss how he managed to make a piece of entertainment built around a real life tragedy in a city that’s notoriously frosty to outsiders, the joys of Gyllenhaal, and how Judd Apatow changed his life.

Stronger hits theaters this Friday.

Every film obviously presents its own unique set of challenges. Which ones stick out in your mind when you think about Stronger?
The hardest part was balancing my efforts to honor a family’s real life story, and an audience’s entertainment.

And how did you manage that?
John Pollono, the screenwriter, had done the preliminary relationships and connections, but I needed them to trust me. I needed to ask them to share with me very vulnerable and intimate details of their lives if I’m going to try to make something authentic. And then there’s that reality to consider. And there’s also the strange efficiency, both economically and just the running time of a film to encapsulate the story. So, there’s a script, and I’m a director that likes to use that as a blueprint and then break away and play with the actors, and play with the environments. And so I had to find that line in production, where the subjects of the film would believe in me and the community would support our project, the city of Boston.

As an outsider, how did you ingrain yourself in Boston, which is such a unique American city with very specific ebbs and flows?
Well, I think it was immediately helpful to not be from Los Angeles or New York, to kind of be a lower-profile regional filmmaker, I think, was comforting to them, because I don’t have any interest in Hollywood exploitation or the clichés of an inspirational story. I wanted to make something that felt honest and genuine, and from the inside. And I’m an outsider. So I needed to have that access. I’d made Pineapple Express, and new Kenny Powers personally, so that helped.

The city’s spirit is very palpable. Do you have a special affinity for Boston after making this movie?
I love Boston. It’s such an outspoken and opinionated community. On day one, we filmed our sequence at TD Garden during the Bruins game. That was our first day of production. We were shooting in a real game, and we asked people to stay after the game, and they’d lost, too. They could have all left but Jake went out and invited everybody to stay and see what we could get, and it was just really moving how many people were there.

What was the mood on set on the days that you shot the marathon scenes?
We shot at the marathon that year. We staged a few things. It was very light and outdoors. It was an ethical thing for me that if we were going to be on Boylston Street, to not actually show anything resembling the event. So when we’re actually in production, it’s actors run this way, actors run that way. Everything’s in sound design and digital effects. It’s distressing. So it was important for me to not ask that specific area to go back there.

I get the impression that Jake and Jeff have developed quite the bond. Is that similar to your relationship with Jeff or is it a little different because you’re approaching this from the point of view of a director instead of an actor?
He sends me ball-busting texts all the time. But I mean, he’s very internal. He’s not a guy that’s just willing to tell you his life story.

He seems pretty comfortable in the spotlight.
Yeah, absolutely. Culturally, it’s not a northeastern thing to just open up and be emotional, so that’s taken exercise for him to embrace that. But he’s hilarious. He’s a really fun dude to hang out with. He’s got that magnetism, and I don’t think he recognized that for a long time.

You’ve obviously worked with some supremely talented actors and I’m sure Jake ranks at the top of that list. What kind of emotional and physical preparation did you watch him go through?
It was a close collaboration like I’ve never had with an actor. I mean, when we’d wrap at the end of the day, we’d go to his house and talk about tomorrow. And rehearsals were extensive, talking about the character, spending time with Jake, going to talk to real people. We invited a lot of real people, initially, as like a counsel for the film. Like, the surgeon. It started with ‘Will you tell us how this went?’ And then at the end of the conversation it was ‘Will you just play yourself in the movie?’ We’d go to see when they fit Jeff for prosthetics, we went up to United Prosthetics and talked to the Martino brothers who talk us through the process. And then we had them play themselves in the movie.

Do you pride yourself on your versatility as a director? It’s almost become your hallmark.
I think so.

When I first saw your films, they were these small, poetic meditations and I thought you were the next Malick. Then you made Pineapple Express.
It’s funny, because I remember when people that know me well saw my first movie, they were like, ‘what is that?’

They expected you to make Pineapple Express first.
Yeah, exactly. The reality of the business is you make something, and they want to see a little bit more of that. And so that was something that I kind of fell into for a couple of movies. If I was going to go from George Washington to Pineapple Express, I don’t know that I would’ve been allowed that opportunity. But then through making a few films that were low-budget and dramatic in nature, I started those relationships, and people did get to know me within the industry, and found that my personality and interests are far more varied than that. So, yeah, Judd Apatow gave me that opportunity, and that changed my life. Just because people were allowed to see me and my eclectic sensibilities. And I think it’s a good thing. I’m not embarrassed about my career. I think it’s just weird.

When you were making those first films, was this your goal? To be working so firmly entrenched in in the Hollywood system?
Oh, yeah. I wanted to make big action movies and westerns. I’m just a movie nerd, so why not make a Star Wars movie? It’d be incredible. But also, I like the environment of this film where there’s four people in a room. And that’s what most of these sequences were, four people in a room. And the intimacy to that is incredible. I made Your Highness, which was a $60 million movie with a crew of 4-500 people, and it’s a very different experience. If you’ve got creative collaborators, people you can trust that are around you, it doesn’t really matter the size. You just want the machine to be hand-curated a little bit.

Do you feel comfortable navigating your way through the Hollywood system?
This sounds weird to say, but I kind of prefer it. I feel like there’s more independence, because I’m a good communicator, and I can speak very clearly about what my opinions are about things.

And you can spot the bullshit.
I can spot the bullshit. But the bigger studios have weeded out the riff-raff, for the most part, in my experience. There’s not a lot of slackers, because they’d be fired. Whereas, you can find a guy in the indie business who’s got his heart in the right place, but he’s lazy, you know what I mean? Those guys don’t survive in the studio system, and I have a low tolerance for slackers and shitty work ethics. I work a lot, and I love it.

Why don’t you live in L.A.? Is that a deliberate choice?
I love talking about movies and I can talk about them all day. But I also love not talking about movies, and I like neighbors that don’t give a shit what I do. Actually, Danny (McBride) just moved from L.A.. I’ve been living in Austin a long time, and Danny was just kind of at the point where he’s like, ‘let’s go try something different.’

Speaking of Danny, I’m so excited for this season of Vice Principals.
Oh, just wait. This season gets dark.

You, Danny and Jody (Hill) have mastered that darkly comic tone. Observe and Report was one of the darkest comedies I’ve ever seen.
It’s so good.

It has a kind of cult status in the same way Cable Guy does, which was almost too dark for audiences.
Yeah, Cable Guy’s a brilliant movie.

But massively overlooked.
Absolutely, and now people pretend it wasn’t. Like Big Lebowski at the time. No one really thinks about the fact that it only made like $10 million when it came out.

And now, if you haven’t seen Big Lebowski, you get sent to an island.
Yeah, exactly. For my career, and Danny as well, and probably James (Franco) too, time does a lot to get the right people, because there’s a machine of marketing that movies come out, and there’s an opening day, an opening weekend, and a campaign. But over time, the right people start to say, ‘You thought one thing, but you’re the right person to see this.’ And so then you start to find where the real strength of a fan base is. And something like Eastbound, every season the viewership would double, not because the show was getting better. It was just because the right people started to watch it and tell their friends that you’re another twisted fuck.

I’d be remiss if I didn’t ask you about Halloween. What are you going to bring to the franchise that we haven’t seen before?
Well, this isn’t a remake, necessarily. This is kind of a different thing.

Will we see Michael Myers in full mask?
Probably. It was funny, I met with John Carpenter the other day to go over script notes. I mean, Danny and I wrote it together. So it’s like these two passionate fans of the original Halloween that don’t want to fuck it up but want to explore it.