The confident and funny Drinking Buddies is Joe Swanberg’s first picture with a real budget (above five figures) and real stars (Olivia Wilde, Jake Johnson, Anna Kendrick and Ron Livingstone), but don’t jump to the conclusion that it’s some kind of rom-com sell-out. The emotional messiness, generational indecision and loose-limbed storytelling of Swanberg’s previous work are all present here, honed and amplified by a terrific cast and sharp production team.

The film has traditional elements: two couples, flirtations and one weekend in the country. But then there’s alcohol — specifically beer — and not just flowing during one climactic meltdown scene. Instead, Wilde and Johnson’s characters work at a craft brewery and seem to have a buzz going at all times, a spirited fogginess that prevents the healthy self-examination they should be undertaking at this moment in their lives. Swanberg very cleverly uses Wilde’s star power and beauty to initially misdirect the audience about her character, allowing his film to quietly develop thoughtful insights into in-between relationships and emotional infidelity. To my mind, it’s Swanberg’s best film.

Released by Magnolia Pictures, Drinking Buddies is already on digital platforms and opens in theaters today. Below, I talk with Swanberg about working with CAA and “going bigger” — how he altered his working methods to work with a larger budget and professional cast. (Full disclosure: Alicia Van Couvering, one of Filmmaker‘s Contributing Editors, is a producer of the film.)

Filmmaker: Drinking Buddies is bigger in budget and in scale than your previous films, and it has real stars. Was all this by design or by accident? When you started to develop this film, did you intend for it to go a different route than some of your others?

Swanberg: I knew that it would be a little bit bigger. It’s the first project I did with CAA, and their attitude was: “We can help you make your movie on a slightly bigger scale. Who are some actors you are interested in working with? What are some stories you’re interested in telling?” So, it came together in a very natural way. But at the size that I was [previously] working, the idea of “bigger” could have meant $100,000 or $1 million. The movies I made before were so small that anything was bigger.

Filmmaker: Did CAA package the film?

Swanberg: I worked with [casting director] Mark Bennett to cast the movie. He did The Hurt Locker and Zero Dark Thirty, so he had great relationships with agents. It was an interesting process getting the gears rolling on an improvised film because no one is used to this way of working. There wasn’t a ton of awareness of my stuff in L.A. either. But, people were willing to give Mark the benefit of the doubt in terms of setting up meetings with this indie filmmaker who didn’t have a script or a title for the movie and couldn’t even really say what it was going to be about other than it was going to be some kind of relationship thing. And then [producer] Alicia [Van Couvering] got involved, very early in the process, in terms of trying to shape it and raise money. So it was a strange, interesting couple of months, meeting with these great actors whose work I admired and then working with Alicia to try and figure out: “What do we say about this? How do we find investors? How do we talk about it? How big is it going to be?” But it all just sort of fell into place in a way that was not dissimilar at all to any of the other movies.

Filmmaker: How did CAA become interested in you in the first place?

Swanberg: When Hannah Takes the Stairs came out in 2007, I got a lot of emails and phone calls from agents. I was already midway through making Nights and Weekends, and I had a sort of punk rock, bratty attitude about the whole thing. I just felt like, “I already know how to make my movies and I don’t need any help. I don’t want an agent.” So if I even bothered to respond to the emails or phone calls it was just to say, “Thanks, but no thanks.” Over the years [CAA agent] David Kopple was the only one who stayed in touch. He kept watching the work, I’d see him at festivals and he’d always make sure to say hi and to let me know that if at any point I wanted to try and do this on a bigger scale that he was really excited to help. So towards the end of 2011, after that huge creative output of, I think, six movies out that year, I felt that rather than another year of trying to do six movies and eeking out a living from all six of them that it might be nice to spend a year working on one movie that I could theoretically make the same amount of money with. And so I sat down with Kopple and said, “How does it work? How do we take this weird thing that I do and this way that I make movies and insert that into the system?” So CAA was involved [in Drinking Buddies] from the very beginning. They have an indie finance department that I worked with, and it was their idea to involve Mark as a casting director.

Filmmaker: What in terms of the content, the material and the way you approached it made Drinking Buddies the one to do on this larger model? To put it another way, could you have done a $20,000 version, and what, aside from the actors, would have been different?

Swanberg: You could have but I don’t know if we would have been able to have access to a brewery for a week. I don’t know whether we could have dragged everyone up to Michigan for three days. It was interesting because as Alicia was putting the budget together I was asking those questions myself. I said to her, “What’s this going to cost?” She gave me a number, and I was like, “Can’t we do it for a fifth of that?” And she showed me the budget and was like, “Quite honestly, no we can’t.” And it certainly wasn’t the actors that cost any money, I’m sure they all lost money. There were just a lot of locations and a lot of infrastructure in terms of what it meant to have an art department, a wardrobe department and all of these things. There was the idea that we could do the $20,000 version of this movie, but why would we if we could do the bigger one?

Filmmaker: You’ve already made another movie after Drinking Buddies on that smaller model. What was that like?

Swanberg: I did this movie in December called Happy Christmas and went back to a five-person crew, and a very loose, quick working method. It was interesting to realize how much freedom I had on Drinking Buddies to ask for things and to get those things. It just costs more money.

Filmmaker: So it was hard to go back?

Swanberg: No, it wasn’t. It was a pleasure. I think that I’ll always be doing that. There are incredible advantages to having no money and very few people around in terms of how quickly we can move and the kinds of artistic risks we can take without having to worry about investors making a bunch of money back. I suspect that’s going to be as appealing to me 15 years from now as it is today.

Filmmaker: In terms of the process, what was the hardest thing about transitioning up to the higher budget on Drinking Buddies? Was there anything about working with the bigger infrastructure that you found difficult?

Filmmaker: I had to write a lot more than I’ve ever written because I realized very quickly that when they opened up the production office there would be these department heads there asking me 50 questions a day. “Should Olivia wear back pack A, B or C?” “Well I think that she should wear C, but it would be great if it were blue instead of green.” “Should Jake’s apartment have this lamp or that lamp in it?” “On the moving day, do we want her to have the remnants of a birthday party or was it a going away party?” “What should Olivia should wear when they go out to eat at the restaurant?” [On previous films] it was just like, “Bring three outfits that you own and we’ll mix and match.” It was a big adjustment having to communicate so much to so many people, things that prior to this I was able to quietly imagine on my own and have a conversation about when I got to set. [This time], I needed to come up with answers to these questions four weeks before we shot. If I wanted Ron’s character to have a really nice record player and a bunch of records, the art department needed time to find these things — and because we didn’t have a ton of money we needed extra time to find them for free or cheap. It was pretty wild to go through a proper pre-production process, where a lot of the decisions of the movie get made before you’re actually making it. But I discovered I really liked it. It was nice to turn up on set and have already answered nine of the 10 questions that needed to be answered that day.

Filmmaker: Did you do anything personally to prep for that process?

Swanberg: Alicia was really helpful in terms of telling me what was going to be expected of me on a day-to-day basis — the kinds of conversations that I would have with the different people in the different departments. She’s done it quite a few times so anything I was curious about she had some anecdote from some other film she’d worked on. The best thing that she said to me was that I was basically going to have to answer questions all day long, 24 hours a day. I just had to have the answers to questions, which turns out isn’t that bad. I found that it was really cool to be able to think about these characters in terms of where they lived, what they wore, what music they listened to, what books they read. I’m used to just making a couple of phone calls and asking which friend doesn’t mind me shooting in their apartment for three days, and then the apartment in the movie is just going to look like whichever friend said yes to the question. So it was really fun that the world of the film was so much richer because I could have specific visions for each one of these characters.

Filmmaker: How did these actors, who are all coming off a lot of other work in the broader TV and television industry, inflect your material? What did they add? How did they transform it?

Swanberg: I’ll tell you the craziest thing, which I didn’t even realize until I got into the editing room: how helpful it is that the idea of continuity is engrained into their bones. Even on improvised takes where take A, B and C would be different dialogue, Ron would still reach over and grab his glass of water at the same point in each scene. They saved my ass [in the editing room] so many times. Beyond that, I think that the more experience an actor has, the more honed they are in their storytelling abilities. The way I work, I paint in broad strokes in terms of the outline and story. So, it’s really cool that the four actors had such practice and experience with throwing in little bits of dialogue that either foreshadowed something or called back to some joke from earlier in the movie. They felt like writers on the set.

Filmmaker: I found the film’s use of Olivia’s star power really interesting. She’s someone who, when you see on screen, you want to like. That her character has some disagreeable, unpleasant elements is something that took me by surprise. I think with another kind of actor, that kind of process of discover wouldn’t have been as surprising. Going into the film, were you thinking about how you you’d play against her persona?

Swanberg: I expect that over the next few years she’s going to be doing a ton of interesting work with a number of great directors and altering the image that has been painted of her. But it was cool to be at the forefront of that, to really get to play against Olivia from Tron and Cowboys and Aliens and these kinds of things. As a filmmaker I felt a tremendous amount of freedom because nobody has seen her like this before, so we could do anything. To have it be the case that she’s so cool, and she wants to be doing movies like this, just made it all that much easier. Her answer was never “no” to these questions. She wore almost no makeup, and she was really excited to get ugly and vulnerable in these different ways.

Filmmaker: What questions did the actors ask you at the start of the process?

Swanberg: Everyone was very curious about how the day was going to go. “What am I going to need to know beforehand? How many takes am I going to do?” Also, we talked thematically about what kind of movie we wanted to make, who the characters were, and what the message was going to be at the end. It was all about trust, making sure in the early conversations that I had reasons to be doing what I was going to be doing. And also, on a film like Drinking Buddies, if the movie stinks then Olivia’s going to be getting most of the heat. She’s going to be the one the general public is going to point their finger at [because] she’s the most visible. I think there’s a big fear [the actors must have]: “If we get a couple days into this and it’s not going well then am I going to have to save this thing? Is the burden of production going to fall on my shoulders if Joe doesn’t know what he’s doing?” With all the actors I sensed that I was going to have to get past that period of “who is this guy and what are these weird, improvised movies he’s making?”

Filmmaker: What did you hand people at the beginning of the process? A treatment?

Swanberg: At the very beginning of the process [the actors] had nothing. Everyone who met with me did so only with the knowledge that I was doing some kind of relationship movie that had something to do with craft beer. By the time they got to set I had written a 45-page script, an internal document so we could schedule the movie and the art and wardrobe departments had something to work from. What the actors got was a two-page, bullet-pointed distillation of that treatment. It had one-sentence descriptions of each scene. That was useful for them because they were making character choices based on the arc of the story. It was good for them to be able see on paper where the movie would go from A to Z. And then on a day-to-day basis they would get call sheets and things like that. But it was really a conversational process on set before we shot each scene, of what I was imagining for the scene but also why it was in the movie. Ben Richardson, the cinematographer, was always part of that conversation too. He was always lighting in such a way that we would have 360 degree or 180 degree access so that the actors did have some freedom to not hit specific marks.

Filmmaker: A lot of movies use alcohol to get people to open up, with epic drunk scenes, but yours is the only film that I can think of where it’s not really about being drunk — it’s about being buzzed. How did the fact that people aren’t drunk, but are always woozy affect the drama?

Swanberg: [Drinking] is part of the world, the craft beer world. It has something to do with the fact that these guys have to taste what they’re making to make sure that the beer is okay. But beyond that it is a sort of a loose, free-flowing part of the culture. But I didn’t quite realize, until I got the first cut of the movie, how much they’re drinking. Spread out over the course of 17 shooting days, it only looks like they’re sipping from beers for a few minutes a few times a day. Then when I assembled it I was like, “Oh my God! They’re drinking a beer in every single scene!” There certainly is a social lubrication aspect to [the drinking], but it was a compare and contrast thing too because Ron and Anna’s characters aren’t buzzed the whole time. It’s Jake and Olivia’s characters who are living in a sort of alternate reality from the people around them; they’re always on a slightly different plane.

Portions of this story’s intro previously appeared in our coverage of SXSW in Filmmaker‘s Spring, 2013 issue.