Armed with a residual check from an episode of Girls, director Richard Shepard purchased plane tickets to Tokyo for himself and the stars of his forthcoming short film, Emmy Award-winner Elisabeth Moss and Ebon Moss-Bachrach.

“It was funny,” Shepard recalls over the phone, laughing mildly at his own antics. “I paid for Ebon and Lissie [Moss] to fly business class, and I flew coach because I was paying for it myself. So Ebon was on my plane, and I kept telling him to go fuck himself every two minutes.”

Once there, Shepard, Moss and Moss-Bachrach, both of whom opted to work without pay, shot Tokyo Project over five days with an intimate 12-man crew, using a free camera, a free editing system and a free score. Many locations were plucked from Shepard's prior experiences in the city: an old movie poster store, a charming bookshop, a bustling café. Often, Shepard would simply have the actors walk the streets and say their lines—no marks, no rules—as the camera shifted in and out of focus, trusting a freewheeling process to capture the energy he wanted. 

“There’s something about doing something for free where no one complains, and everyone’s trying to come up with a creative solution,” Shepard says. “I can ask Lissie Moss to change in the backseat of a car and she’s like, ‘great.’ That couldn’t happen on a feature. It felt in a weird way like a student film, except everyone knew what they were doing.”

The result is a melancholic half-hour romance, as much about the love between its two characters as it is between Shepard and Tokyo, evinced in his twinkling, dreamlike shots of the city at night. Revolving around a traveling businessman’s encounter with an enigmatic American photographer, the film may call to mind Sofia Coppola’s Lost in Translation. In reality, though, the short is more reminiscent of Shepard’s work on HBO’s Girls, where he directed several of the show’s widely-acclaimed bottle episodes—themselves short films in spirit—such as “One Man’s Trash,” “The Panic in Central Park” and last season’s instant-classic, “American Bitch.” 

Fittingly enough, Tokyo Project counts Girls creator Lena Dunham and her creative partner Jenni Konner (also Shepard’s longtime girlfriend) as executive producers. While Shepard primarily made the film to satisfy his own artistic ambitions, it premiered at this year’s Tribeca Film Festival and was fortunate enough to be picked up by HBO, where it premieres this Saturday.

Recently, I had the pleasure of talking to the filmmaker about directing shorts over features, working with Dunham and his ongoing love affair with Tokyo. 

I don’t mean this as an insult, but I actually found most of the short to be quite vexing. Then you get to the end and it casts the movie in an entirely different light. It kind of reminded me of some great short stories, where the last line kind of alters the meaning of everything you’d read prior. Which is a roundabout way of saying I enjoyed it.
It definitely felt like a short story to me when I was writing it. And I do enjoy that feeling where you’re carried into the storytelling but then you look back and go, “Oh, well that’s why that happened.” In a way you have to put pieces together to make the story work, and then at the end it shows you the pieces that really went together. I think that’s fun for the audience.

What was the germ of this idea for you?
I’ve been really wanting to write and direct something romantic for myself. And even though I’d been directing on Girls and doing a lot of work with great people, I hadn’t written and directed a movie in a few years. I was itching to have an experience where I lived and died on my own creative choices.

I was also in love with Tokyo. It was one of those cities where the second you land, you’re like, “I want to shoot everything." Many of the places that are in the movie are places I discovered visiting Tokyo, whether it be the old movie poster shop or beautiful book store or the coffee bar. Those places really zipped and I really connected to them. And then I had an idea for this love story...I think when you travel and you go to new places, in a way everything is new. I don’t know if this makes any sense, but you know when you’re in high school, every day feels like forever? And when you’re in regular life it just speeds by? When you travel a day can take forever again, because you’re taking in so much information and having so many experiences. You’re living twenty days in one day. I really liked that idea, in which you can reinvent yourself and be open to anything. You do things things [when you travel] that you would probably never do in your normal life.

What was it like working with Elisabeth Moss and Ebon Moss-Bachrach? How did they get attached?
I really love Ebon as a human being and I think he’s just a great actor. His role on Girls [as Marnie’s boyfriend, Desi] was so indelible and so funny, but it was certainly not who Ebon is. And I thought there was a more doleful side to him. So I wrote this for him thinking maybe he would do it.

For Elisabeth Moss, when I finished the script I gave it to Lena Dunham to get her notes and she loved it, and I said, “Will you help me get an actress for a role?” and she said, “Yes, who do you want?” and I said, “I want Elisabeth Moss.” And she’s like, “Well, let’s call her and see if she’ll be in it.” So we just cold-called Elisabeth Moss. I guess when you’re a celebrity you can just call other celebs and they’ll take your call. But god bless her, Lena got Lissie to read the script and she really responded to it. We met in New York and I think she understood that it would be a unique experience, the fact that we were going to shoot it with a crew of 12 people, that we were going to shoot it in five days, that we were going to go to Tokyo and shoot for 12 hours, have a delicious dinner, drink some sake, take an Ambien and go to sleep, wake up, drink a lot of coffee, go to set, work really hard and repeat the whole thing every day. It was just us. And that was a very unique way of making a movie.

I know you’ve directed features before (like Dom Hemingway and The Matador). What attracted you to this format? It’s not really dissimilar, it seems, from some of the bottle episodes you directed for Girls.
There’s definitely an inspiration from those Girls episodes—to believe that you could tell a really emotional story in 30 minutes...I did feel there was something nice about short storytelling. Also, from a purely professional point of view, if you’re making a feature...First of all, it’s so hard to get a movie made, but second of all, the pressure on you is unbelievable, because you’re spending a ton of money and you’re going to have to return the money to your investors. The idea of experimentation diminishes with each dollar sign you put on the product you’re making. So for me the idea of, “Can I do a short for basically no money?” took away all the pressure of having to make something that’s responsible to anything other than my own creative happiness. 

I’m curious what movies, if any, inspired you here directly? I know there were stills and clips interspersed throughout the short from Japanese movies, and there’s a more direct reference to Don’t Look Now. Obviously, Lost in Translation came to mind, too, as a pretty seminal Tokyo love story...
Well, I purposefully didn’t watch Lost in Translation. I hadn’t seen it in awhile and I purposefully didn’t watch it, because I wanted to have my own experience of writing the movie. I’m obviously inspired by movies and I love Japanese cinema, and all of the clips I got to show were from movies I loved. But Tokyo Project wasn’t so much inspired by other movies as it was just inspired by my love of making movies. I just happen to love the process so much. And when actors or crew members are doing a movie for free, everyone is working on a different level. Even in movies in which people are loving the process from beginning to end, somewhere in your mind it’s a job. There’s something about doing something for free where no one complains, and everyone’s trying to come up with a creative solution. I can ask Lissie Moss to change in the backseat of a car and she’s like, “Great.” I can say, “Lissie we’re taking a subway somewhere but we’re going to film you on it but we don’t own it”—and she’s like, “Great let’s go.” That couldn’t happen on a feature. It felt in a weird way like a student film, except everyone knew what they were doing.

I was also inspired by this idea of trying to use what I had learned on Girls. So right after we filmed “The Panic in Central Park,” which was a very romantic episode and all handheld and all through New York, was when I wrote Tokyo Project. Normally on a movie you rehearse the scene and you put marks on the ground and the actor has to hit the mark completely right, because that’s where the light hits them. But on that episode of Girls we had no marks on the ground, we just let Allison [Williams] and Chris [Abbott] do what they wanted to do and the camera caught them and they had these moments. I really wanted to have that feeling when I was filming in Tokyo.

[Ed. Note: the following question and answer contain spoilers.]

You ride that tricky line between deceiving your audience and delivering a well-earned plot twist at the end. How did you navigate that?
When we were editing, there were some notes coming back from friends. Sometimes people were like, “Why is Lissie being so weird with him, why isn’t she being friendlier?” And we tried a version that softened her up a lot for the first part of the movie, which worked for the first part of the movie but destroyed the ending. I chose to do the more difficult version, which is to have it be a little troubling for the audience as it’s going down, but hopefully keep them involved through the sheer movement of the filmmaking, and then at the end have them go, “Of course that’s why she was cold, of course that’s why she acted that way, of course that’s why that happened,” because of what they end up learning at the end of the film.

I think filmmakers can take an audience places they don’t necessarily want to go or are uncomfortable going, if it feels like at least the filmmakers know what they’re doing. I always say that it’s about feeling like you’re in capable hands. Which is why the first few minutes of a movie are so important. If you suddenly think that the director doesn’t know what he's doing, then you’re not willing to go anywhere he wants to take you.

I know Lena Dunham and Jenni Konner exec-produced this. How involved were they creatively?
Lena and Jenni both read the script and gave me some the notes, and they helped me get Lissie Moss. Then I showed them the first cut and they gave me a huge amount of notes. So they did in a weird way exactly what an EP is supposed to do—get you your movie star and help you, at the end, make your movie as good as possible. I loved collaborating with them.

I made a movie about four years ago called Don Hemingway and Lena gave me copious notes. She’s really smart about post-production and ways of fixing things and solving issues and certainly on this movie, the notes they both gave were very incisive in terms of helping form the movie. Because I didn’t have a studio, I didn’t have a network and I didn’t have anyone else to have sign off on this, I was looking to them...because the worst thing you can do as a filmmaker is not want to hear any comments. 

Any fun anecdotes that came out of this ragtag production process?
We could shoot in neighborhoods that don’t normally have movies shot there, because we didn’t have a truck. So we were shooting in an area that was basically controlled by the Japanese mafia, the Yakuza, and the Japanese crew said that if at any moment we tell you to stop filming, you have to stop filming. We were shooting all night and at one moment we stopped in front of this shop to get a shot. A lot of the Yakuza dress in this 1950s sort of way, they look like they’re almost extras in Grease or something. It’s very strange. And suddenly this guy came out in his suit and he said something to our Japanese assistant director, and the AD literally looked like he was about to faint. And he was like, “We have to move NOW.” You’ve never seen a group of people move more quickly.

This conversation has been edited for clarity.