Beginning with her first feature film, Sydney Freeland has striven to create and present accurate, compelling images of Native American and Indigenous people on screen.
2014's Drunktown's Finest, which she wrote and directed, told the story of three people overcoming the challenges of life on a reservation. It was nominated for the Sundance Film Festival's Audience Award and went on to receive the Jury Prize at L.A. Outfest.
Freeland is now at work on a landmark project, the first-ever broadcast television network show centering on Native Americans. NBC has given the green light to a put pilot for Sovereign, which Freeland co-wrote (with Shaz Bennett) and has signed on to executive produce with Bird Runningwater and Ava DuVernay under DuVernay's production company, Array Filmworks.
After growing up on a Navajo reservation in New Mexico, Freeland graduated from the Academy of Art University in San Francisco and attended a writers' program in Santa Fe before she was accepted into the Fox Writers Lab.
Then, with a film degree but no job, she went back home to the reservation — but not for long.
Freeland was in the parking lot of a Walmart in Gallup, New Mexico, on a Friday night when she got the phone call that would set her career in motion. It was from a TV producer who had received her resume, asking if she could meet him at the Starbucks in Westwood that Sunday. She packed a bag and hit the road for L.A. During the meeting, she nailed down the job as a production assistant on a cooking show.
The rest, as they say, is on her filmography. She directed all six episodes of the Emmy-nominated web series Her Story. Her second feature film, Deidra and Laney Rob a Train, premiered at Sundance in 2017 and is currently streaming on Netflix.
Her television directing credits include The Wilds, Rutherford Falls, Grey's Anatomy, P-Valley, Nancy Drew and Fear the Walking Dead.
She — and the industry — have come a long way since she struggled to make Drunktown's Finest. Securing financing while remaining true to her creative vision was not easy. At one point, the main investors wanted her to change a character from Native to white, or half Native and half white.
"Compare that to today," she says. "I've directed a couple of TV shows with Native content, and the conversations with the showrunners are about, 'How do we get this right?' On the Native side, being open and being collaborative, I see what I hope is a genuine shift of execs and showrunners of getting it right. For me, that contrasts wildly with the first feature film, which was, 'Make it white, so we can sell this thing.'"
"When I started that first feature, it came from the idea of not telling a white savior story or to have simple characters. I grew up in a diverse and dynamic place, and wanted to show that, which led to three different characters: a straight Navajo guy going off to the military, a woman adopted by white people and a transgender woman trying to get off the reservation."
Freeland, who is also transgender, points to her experience directing episodes of the Grey's Anatomy spinoff Station 19 as another example of moving the needle. "I brought up in casting to make one role Native, a character found in a park, a non-descriptive role," she says. "Even having that was great, and little things over time can add up."
She still has memories of watching John Wayne movies with her father. "A lot of those are sort of racist caricatures — the antagonist, the gentle archetype, the wise elder or the warrior," she says. "Beyond that, there were white actors portraying Natives. It was a weird thing. Everyone knew it was inauthentic and not the actual experience, but any representation was great."
Starting off in the business, Freeland felt like most others had a head start and that Hollywood was a monolith with gatekeepers. Still, she broke through barriers through persistence and resilience.
"There's no one way in to the industry," she says. "You just have to be willing to put in the work. I didn't know or wasn't related to anyone, and didn't pick up a camera until I was 24. Learning to cope with and accept rejection is the norm in the industry. Dust yourself off and look at things and try to improve. Creatively the best advice is every rejection is an opportunity to make content better."
From not knowing anyone in town, Freeland now has many close colleagues, including Sierra Teller Ornelas, co-creator of the Peacock comedy Rutherford Falls co-creator, and Sterlin Harjo and Taika Waititi, co-creators of the FX comedy Reservation Dogs.
"It's a small community, and we all know each other. Sierra and I are the same age and went through the same program, and now she's a showrunner. How great is this? Sterlin Harjo comes from indie film, and we share war stories. Over the past few years we've interviewed for the same projects. We'll call each other afterward and download information," she says.
She directed four episodes of the first season of Rutherford Falls, and during the first season of Reservation Dogs, she was on the writing staff and directed two of the eight episodes.
“Everyone in the [Reservation Dogs] writers’ room knew each other, and we are all friends and colleagues, so it was a familial feeling," she says. "Once we got to shooting, Sterlin pushed for Native inclusivity in the production both in front of and behind the camera, so it was a very welcoming environment.”
She is currently working with Harjo on the screenplay for Rez Ball, a Netflix film about a Native American high school basketball team, which she will also direct.
And in addition to her work on Native-themed projects, she joined one of the best-known science-fiction franchises of all time when she directed an episode of Star Trek: Brave New Worlds, a new series scheduled to premiere next year on Paramount+.
“It was an absolutely amazing experience with the cast and crew, a great script and fantastic special effects,” she says. “Although it follows the crew of the Enterprise before Captain Kirk, there will be some familiar faces, and it is in the spirit of the original series.”
Freeland transitioned in 2004 before beginning film school in San Francisco, where she found a welcoming support system. She says trans awareness has improved enormously since she entered the business and points to 2014 as an inflection point, when Laverne Cox was on the cover of Time magazine and Caitlyn Jenner made headlines with her transition.
“Now it’s become part of the cultural fabric of America — not that there aren’t things to work on," she says. "I’ve been in awe of how things have progressed in terms of trans representation.
“I gravitate toward marginalized, sort of outcast people outside the margins, and those are the stories that are becoming popular right now,” she says. “That wasn’t always the case. I’m excited about how many trans filmmakers and actors there are. There was a point I could name every one, and now I don’t know half the people, which is a sign of how far the industry is coming.”