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Director Sydney Freeland on Trans-centric Web Series “Her Story”

A web series about a couple of Los Angelenas discovering love when they least expect it sounds less “groundbreaking” than stereotypical indie pitch. Yet “Her Story,” which debuts its first six episodes on its website (for free!) on January 19th is anything but your average hipster cliché. The series, co-written by Jen (“I Am Cait”) Richards and directed by Sydney Freeland (whose rez-set feature film “Drunktown’s Finest” made a splash at Sundance a couple years back) also features trans women in the lead roles. Meaning the talented ladies both in front of and behind the lens are all part of the transgender community. Recently, I had the opportunity to catch up with series director Freeland – who I last interviewed prior to the “Drunktown’s Finest” 2014 premiere – to learn more about “Her Story,” and her own story about the process of portraying a once marginalized, increasingly visible population in a realistic light.

Lauren Wissot: So how did you come to get involved in the project?

Sydney Freeland: Sarah Baker, who is one of our producers, sent me the script. I knew Sarah from “Drunktown’s Finest” because she was also the manager of one of the lead actors in that film.

LW: What’s the ratio of trans-to-cis cast and crew? (I know the series is written by/directed by/starring trans folk – but someone like executive producer Eve Ensler obviously falls into the latter category.) And how did this affect the production process, if at all?

SF: I couldn’t give you an exact number, but I can tell you that we had trans crew involved with every phase of the production. One area in which I was particularly blown away was with the music. We ended up with four trans musicians on the soundtrack – Isley Reust, Rie Daisies, Namoli Brennet, and Mina Caputo. With Isley (and her band Spectacular Spectacular), they actually wrote an original song specifically for “Her Story.” We were so impressed that we even shot a music video for it.

LW: The transgender community is every bit as diverse as the community that identifies as lesbian or as gay, so I’m wondering what it was like to work with so many trans folk both behind the scenes and in front of the lens? Were there differing opinions when it came to the portrayals of these characters?

SF: I do think there was a very familial vibe on set. We were moving at a relatively fast pace so there wasn’t a lot time to stop and think, but I do remember looking up from time to time and thinking, “This is nice.” You don’t always get that.

LW: I believe your feature film “Drunktown’s Finest” largely originated as a reaction to the media’s stereotyping of your Navajo reservation community. Do you see the series in a similar “activist” vein?

SF: What jumped out at me initially was Jen and Laura’s script. I remember reading it for the first time and thinking, “Wow, I didn’t even know I wanted to do this.” What I really loved was that this was a story about the trans community, but it wasn’t about transition. At its heart it was a love story, but we were picking up with these characters years later. On a personal level this was also something that I related to. I transitioned over 10 years ago, and I found myself really connecting with what the Violet and Paige characters were going though.

LW: What challenges did you face shooting a web series as opposed to a short or feature-length film?

SF: Time. Because this is a web series, our audience will likely be watching this on a computer or mobile device. This means there is a much greater chance our audience will be distracted, so the challenge for us was to make the story as engaging as possible, as quickly as possible. Thankfully, we had a fantastic editor in Bryan Darling. At one point the first episode was 14-minutes long and he literally slashed it in half to 7 minutes. At first I was terrified that we were losing all this important set-up and character info, but the more I watched the more I realized that he was right and we didn’t need all the set-up. That was definitely a challenge, but I feel like we found a nice balance between story and pacing that really caters to the web series format.