Queer filmmaker, film historian, archivist, and writer Jenni Olson’s acclaimed documentary short film, 575 Castro. St., which originally world premiered at Sundance in 2009 and received its international premiere at the Berlinale that same year, is being revisited and celebrated by both festivals with retrospective screenings. Olson’s film is a contemplative yet urgent meditation on history and politics which feels especially resonant in today’s charged climate for the LGBTQ+ community.
Last month saw the film play at Sundance as part of its Park City Legacy Short Film Program. Next, it will screen at the 2026 Berlinale in the Constellations of Queer Memory: 40 Years of the TEDDY in the Short Film Form program on Saturday, February 14th and Sunday, February 15th, as part of the 40th Anniversary TEDDY Award lineup.
575 Castro. St. is an indelible stylistic achievement, employing haunting imagery focused on the light and shadows playing on the walls of the Castro Camera Store, recreated as a set for Gus Van Sant’s Oscar-winning Milk. In counterpoint, the soundtrack features Harvey Milk’s eloquent personal and political reflections, shortly after his election to the San Francisco Board of Supervisors in 1977, making him one of the first openly gay elected officials in the United States. He made the audio-cassette with the intention that it be played, “in the event of [his] death by assassination.” The film features Milk’s now legendary line, “Ya gotta give ‘em hope,” and his eloquent denouncement of right-wing anti-LGBTQ hate, calling out Anita Bryant and California Senator John Briggs. Milk and San Francisco Mayor George Moscone were assassinated by SF Supervisor Dan White one year later, in November 1978.
“Harvey Milk was such an incredible LGBTQ movement leader and activist. Nearly 50 years later, his wisdom of 1977 feels extremely timely in our current political landscape, as LGBTQ people, and especially trans people, are being so viciously targeted with fearmongering and hate from right-wing politicians and media,” comments Olson.
For over three decades Olson has been an integral part of queer cinema culture in the United States. As well as being an acclaimed and award-winning filmmaker in her own right, she was co-director of the world’s longest running LGBTQ film festival, the San Francisco International LGBTQ Film Festival, now Frameline. She went on to be director of marketing at Wolfe Video, and co-founded the pioneering online platform PlanetOut.com, and created Butch.org. She’s written about film for Filmmaker Magazine, The Advocate, The San Francisco Bay Guardian and NewNowNext, and authored The Oxford Handbook of Queer Cinema.
As an archivist, Olson has built a collection of LGBTQ+ marketing materials, 35mm trailer and film prints, rescuing many from obscurity; a collection that was acquired by the Harvard Film Archive. Olson served as an archival producer and story consultant on the four-part HBO Max queer history docu-series Equal. She is also co-director of The Bressan Project, which is devoted to digitally restoring and rereleasing the work of pioneering Buddies filmmaker Arthur J. Bressan, Jr., including his gay adult features Forbidden Letters and Passing Strangers starring Robert Adams.
Following The Queer Review’s expansive career interview with Jenni Olson in 2021 focused on the Criterion Channel’s major retrospective of her contemplative 16mm essay films, here the filmmaker reflects back on the making of 575 Castro. St., the initial reaction to the film, contemplates its legacy, and shares details of her upcoming third feature film, Tell Me Everything Will Be Okay.
What was the genesis of the film?
Jenni Olson: “I will be forever grateful to Peter Bowen who commissioned me to make the film as a short for the official website of Gus Van Sant’s Milk. Peter had been the longtime editor at Filmmaker Magazine, and he was then running the Focus Features website FilmsInFocus.com and coordinating the creation of content around their various releases. I was honestly really surprised when he asked. Given the kinds of films that I’m known for, it was a bold choice for them to make. My features—The Joy of Life and The Royal Road—both of which also premiered at Sundance, in 2005 and 2015 respectively, are composed entirely of long-take exteriors. My aesthetic approach for 575 Castro St. definitely has the same ethos and style, though in this case it is entirely long-take interiors.”
“Gus Van Sant’s team had done very ambitious production design work on much of that block of Castro Street to make it all look like 1977 to 78. After I agreed to do the film, I did an initial scouting of the area thinking I would shoot outside. But when I walked into the Castro Camera store set, which was of course the main set for the film, it felt immediately clear that I wanted to shoot those interiors.”
“It was a huge honor to be making a film that would be associated with such a big Hollywood movie and Milk went on to win Oscars for Best Actor for Sean Penn and Best Screenplay for Dustin Lance Black.”
How does 575 Castro St. fit into your essayist style and overall artistic vision?
“In all of my work, my cinematic approach of shooting these contemplative, mundane urban landscapes is very intentionally crafted as a way of foregrounding the audio track. As a viewer, it’s not often that you get to have an entire film that is so much about simply being spoken to. As a filmmaker, when the visual track is so minimalist, I love that you can create such a huge impact on the viewer through very small things. For instance, especially in that last very long shot of 575 Castro St.—which is nearly three minutes long, literally almost half the film—you’re seeing the play of light and shadow on the wall. And, at least for me as a viewer, you feel almost hypnotically drawn into Harvey’s voice in a way that matches the waves of light which are being generated through the front window as the cars are going past on Castro Street. It enhances the emotional impact of his words in a really remarkable way. Creating this kind of visceral impact on the viewer is something I’m always working with in different ways in my films.”
“There are two main ways that 575 Castro St. stands out as very different from my other films. Firstly, that all of my films feature an essayistic voiceover that is either literally or essentially my voice or my persona. In my standard mode of earnest butch dyke pining over unavailable women and reflecting on arcane aspects of American history. Secondly, I shot this film on HD digital, when I usually shoot on 16mm film. I wish I would have had that kind of budget for 575 Castro St. Working in 16mm film is one of the most distinctive aspects of my vision as an artist.”
“Speaking of which, I also want to say it’s especially meaningful that 575 Castro St. is being given so much attention like this right now because I’m currently in production on my new 16mm feature-length urban landscape essay film, Tell Me Everything Will Be Okay. During this formative and grueling part of the filmmaking process, it’s nice to be reminded that there are people out there who really do want to see your work.”
What are some of your filmic and artistic influences?
“My main cinematic influences are definitely the durational experimental works of people like Chantal Akerman and my friend William E. Jones, whose 1991 film Massillon—which is also a 16mm landscape essay film—had a really big impact on me. I got my B.A. in Film Studies from the University of Minnesota that same year. I remember watching Akerman’s Jeanne Dielman in one of my classes a few years before that and being so amazed at how it affected me, particularly the durational aspect of holding shots and putting the viewer into this almost meditative bodily state. I think my work is very much in this tradition. I like to say that I aspire to make the mundane heroic. I want to give viewers a way of seeing, and being present with their own emotions, that they can take out into the world when they leave the theater. Other filmmakers whose work has influenced mine include Su Friedrich, Sadie Benning, and Marlon Riggs. I’ve also been strongly influenced by the poetry of Frank O’Hara and the French Symbolist poet Jules Laforgue. In fact, my new film incorporates work by both of them.”
What was the initial reaction to 575 Castro St. at its premieres at Sundance and Berlin?
“We launched the film in this huge way, starting off at Sundance and Berlin, and then played tons of important film festivals—straight and queer—and the response was so wonderful. Speaking of the Berlinale, in 2021 I was very honored to be recognized with the Panorama’s Special TEDDY Award for my decades of work as a filmmaker and as a champion of LGBTQ film and filmmakers. During the festival run, audiences and critics said over and over again how deeply moved they were hearing Harvey speak in such an intimate, eloquent, powerful way and with such a timeless and ever-timely message about how important it is to be out and to stand up to those who attempt to oppress us.”
“The absolute best thing was that my kids were in grade school and middle school at that time and for several of those subsequent years I did an annual presentation on Harvey Milk Day—which we celebrate here in California on Harvey’s birthday, May 22nd—where I would show the film and talk with their class about Harvey and his important work. It brings tears to my eyes even thinking about it. It is so important for young people to know that there are LGBTQ heroes like Harvey and that they get to experience this very simple message that it is okay for you to be who you are, and that you should respect and appreciate other people who are different than you.”
575 Castro St. speaks directly to a crucial moment of LGBTQ history in the United States. Outside of the U.S., what significance does your film have, especially in today’s political climate?
“Imagine being an activist or a political leader living in a time where there’s such a palpable likelihood of being assassinated that you feel compelled to record your own last words like this. I think we are living in such a time once again today. I hope that LGBTQ movement leaders across the globe will be inspired by Harvey’s passion and earnestness, along with all of us activists and organizers and regular people who are fighting for our rights as LGBTQ people and for the rights and safety of so many others who are under attack. May we all be as courageous as he was in standing up and speaking out.”
“Speaking of which, as Utah just hosted its final Sundance Film Festival there’s a big news story related to Harvey Milk. In a bigoted provocation worthy of the anti-LGBTQ figures of Harvey’s era, Utah Republican Representative Trevor Lee—who sponsored a bill last summer to ban the Pride flag and who has a long anti-LGBTQ history—just introduced a state bill proposing that Salt Lake City’s Harvey Milk Boulevard be renamed for Charlie Kirk. One of the things Harvey talks about in the tape is the anti-LGBTQ fear-mongering of Anita Bryant and California State Senator John Briggs, whose Prop 6 “Briggs Initiative” would have banned gays and lesbians from teaching in California public schools. This guy seems like the Briggs of Utah, 50 years later.”
What else can you share about your upcoming film, Tell Me Everything Will Be Okay?
“Like my two other feature-length 16mm essay films, it’s a digressive exploration of a range of topics. I reflect on growing up queer and gender non-conforming in Minnesota, grappling with the Stoic character traits of my Scandinavian heritage, the power of identifying with fictional characters, and the joy of pining over unavailable women. I’ve been shooting with my regular cinematographer Sophie Constantinou here in the Bay Area and I also went back a few months ago to shoot a bunch in Minneapolis and St. Paul and the teeny-tiny suburb where I grew up, Falcon Heights.”
“The footage is really gorgeous, if I do say so, very similar to my other films; these simple compositions of streets and buildings and industrial decay. It always seems a little crazy that I continue to shoot on film but there really is just nothing like it. The quality of the 16mm film image is a huge component of my aesthetic as a director; the saturated color and the grain, as well as the aspect ratio. I just love the 4:3 format, which is like the opposite of wide-screen, basically more like a square framing, like an old movie. Similarly, the grain of 16mm is pretty much the opposite of digital. I’m very attached to the fact that this is an analog format. It’s amazing, the film physically exists.”
“This is completely interconnected to themes in my work about history and nostalgia and that I’m trying to help the viewer remember that we physically exist. I have a section in The Royal Road called “In Defense of Nostalgia” where I describe nostalgia as “an attempt at mindfulness. It’s a strategy, in this exceptionally digital age, for staying connected to the physical, analog world in which we live. By reconnecting us to our humanity, I believe nostalgia could be the very thing that saves us.”
“It’s always a little hard to describe my films. They’re “about” certain topics, but what I’m trying to do cinematically in the storytelling and approach and larger themes is the more interesting thing that they’re “about.” Which is much more ambitious. This sounds a bit grandiose, but I’m trying to bring my audiences into their own understanding of vulnerability as a path to self-acceptance, nostalgia as a key to lost wisdom and returning us to this moment, and storytelling itself as a mode of survival. Ultimately, I think I’m trying to give people a kind of cinematic therapeutic experience. Which is really what any good movie should be.”
575 Castro St. world premiered at the 2009 Sundance Film Festival and screened at the 2026 edition of Sundance as part of the Park City Legacy Short Film Program. The film will also be part of the 40th Anniversary TEDDY, TEDDY 40, at the 2026 Berlin Film Festival running February 12th – 22nd in the Constellations of Queer Memory: 40 Years of the TEDDY in the Short Film Form program screening on Saturday, February 14th at 7pm and Sunday, February 15th at 1pm at Zoo Palast 2.
575 Castro St. is also available to watch online via Kanopy, Vimeo, and YouTube.
For more on Jenni Olson head to her official website, and follow her on Instagram @JenniOlsonSF , Vimeo, and Facebook.
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