Andy Ostroy on Keeping a Singular Artist’s Legacy Alive in “Adrienne”

There’s a video of Adrienne Shelly filmed on the occasion of her 30th birthday in “Adrienne,” talking with a friend (revealed in the end credits to be future “Capote” director Bennett Miller) about doing something meaningful with her life. It was 1996 and Shelly had become primarily known for her unforgettable performances in Hal Hartley films such as “The Unbelievable Truth” and “Trust,” her curious spirit radiating off the screen as characters who wondered if there was something more out there for them when clearly she would ask the same question of herself. It made her an irresistible presence on screen, but she was equally invested in making something happen behind the camera as in front of it, taking the lessons learned from Hartley’s scrappy independent productions to direct her own.

Andy Ostroy only got to experience some of this creative restlessness, having met Shelly in 2001 after the Hartley years and her first two features “Sudden Manhattan” and “I’ll Take You There,” both warmhearted and wonderfully eccentric comedies that failed to catch on in the way their director had hoped, and beyond getting married and having a daughter together, the two could look forward to Shelly’s development of “Waitress,” a promising Southern-fried comedy that she had been cooking up about a talented pie slinger trapped in a bad marriage. Tragically, Shelly would never get to see the massive success that “Waitress” would become, a sensation at Sundance starring Keri Russell that would be adapted into a Broadway show that still runs today, after she was murdered in 2006 during an attempted robbery. But Ostroy dedicated himself from that day on to making sure her memory continued to live on, founding the Adrienne Shelly Foundation, which has provided the seed money for countless female filmmakers to get their initial work off the ground, and now has generously offered the gift of a few more hours in her company with “Adrienne,” a feature that acknowledges the staggering loss of Shelly just as she was hitting her stride, but celebrates all that she was able to accomplish and continues to with the legacy she left behind.

Visiting with friends, family and creative collaborators, Ostroy learns that his wife had always been in a hurry to make a mark, concerned with her own health ever since her father died of a heart attack when she was 12, and playfully described by friend Pamela Gray as “an old lady in a hot chick’s body,” Shelly proved to be a force of nature coming out of college, who parlayed the success of starring in “Trust” to starting her own theater company and pursuing her own work as a multi-hyphenate. With the impact she made on the entire New York creative community demonstrated by the sheer number of people Ostroy talks to in “Adrienne,” and their ongoing effort to try to make sense of her unthinkable death, the film sees her husband selflessly investigating the circumstances around her murder, going so far as to set up a jailhouse meeting with Diego Pillco, the man who took her life. What emerges from all of it is perhaps the greatest tribute of all when Shelly spent her life resisted being judged by her appearance and throughout the film, the truth is more complicated than it appears on the surface.

Following the film’s premiere at DOC NYC, “Adrienne” is making its way onto HBO this week and Ostroy graciously took some time to talk about why he went ahead with such an emotionally demanding project, what it was like to uncover archival materials for the project and the continuing work of the Adrienne Shelly Foundation that has encouraged so many artists to move forward in their careers.

Was there something that made this the right time to take this on?

The major catalyst was when I had taken Adrienne’s mother to see the musical “Waitress,” and she got to talking before the curtain went up with a few out of town people behind us. Eventually, she shared that her daughter was involved in this show, and she told them Adrienne’s name, and they responded with, “Oh, that’s great. Is she here tonight?” And it got me thinking, of all the 1,100 or 1,200 people sitting in the theater, how many of them really knew who Adrienne was? That was the real trigger to set out on this journey to tell people who she is. In the film, you see me go to the line outside the theater to validate or disprove my theory, and of course most of the people said they didn’t know who she was.

It seemed throughout you were learning things about Adrienne as well from before you met her. What was it like diving into this?

I definitely learned a lot, as did my daughter who was on a lot of the shoots with us. I had only been with Adrienne for five years, so she had a life before me. She had a childhood, the college years, the Hal Hartley early acting period, and then her transition into writing and directing, so other than what she had told me on some level of in the five years that I was with her, I really didn’t know that Adrienne as well as I wanted to, so the film gave me the opportunity to fill in those blanks.

And I always had a strong vision for the film and that was life, death, aftermath. Obviously, the life is largely biographical and fortunately because she was an actor and a filmmaker, there’s a lot of archival material that existed in addition to what I had, just home movies and stuff. The death, which is a smaller part of the film, but also archival exists, and then the bigger challenge was to put together the aftermath piece, [which] involved interviewing a lot of family, friends, people she worked with and people associated with the crime. The real challenge became weaving those three themes together in a cohesive way that was also balanced and moved the story along.

When you were so close to the story and it’s your first time making a film, did you have a team around that could help keep perspective?

Well, I’ve done a lot of writing over the years, and when you are a writer you self-edit, so there were certainly some disciplines that I had done and been involved in that gave me some confidence, but I had not worked on a film like this. I had a strong vision and I think having a vision matters with anything you do, more than anything, and I surrounded myself with great people — the team at HBO and Blowback Productions, they really were behind me and very passionate about the project from day one, and together we made a film.

I was quite taken with some archival material that was filmed by Bennett Miller, a friend of Adrienne’s, that appeared to be an interview, but far more intimate than for some professional project. How did you get your hands on that?

That’s a good question because for years I stared at all formats of old tapes on my shelf, and I had no reason to do anything with them. There was a point before I made the film where I was considering just putting them in storage. Then when I decided to make the film, I took them all down and we digitized them and immediately realized that there was gold up there in that shelf, and that was one of them. I spent so many hours going through those tapes and one by one realizing, “Oh, my goodness, there’s just incredible material here.” And that because she was a storyteller and a filmmaker, she did naturally have an inclination to put some thoughts on tape and record herself and do it with friends like Bennett Miller. That’s what storytellers do, they memorialize things. And fortunately she did that, and those moments became incredible moments in the film.

One of the beautiful elements of the film involves excerpts from an unfinished documentary she was making about happiness. How far along was that project?

She did a lot of interviews and she went on a couple of missions to sit with organizations that were all about happiness. It’s comical, some of the stuff that I found. People who wrote books on happiness, she would go interview them. And then at Barnes & Noble there would be 20 people that would come and sit and listen to an author talk about their book, and just regular people talking about happiness and Adrienne was there with her camera filming it. It’s incredible stuff, and it was half-serious, half-comedy, which is how she did everything. But that project was something that I believe she did as a struggling artist in between jobs, so it was like, “I have a camera, it doesn’t really cost much money, so that’s what I’ll do to kill time.” She was serious about the subject matter because it resonated with her own life at the time as you see in the film, but I think the funding came through for a feature film and she was like, “Okay, I’ll put ‘Happiness’ aside and make my other movie.” And then she just never picked it up again, but there’s a treasure trove of material there.

Was it always in mind to reach out to the man who killed her?

It was. He had told a lie when he was arrested during his confession. He had told a lie at his sentencing, and I felt very unsettled over the years, and being wired the way I am with my education in journalism, I knew that I couldn’t remain settled and I had to seek the truth and write about it, and I knew that there was only one person alive who could tell the truth about what really happened that day, and that was him, so I knew that I would have to go see him.

When I started to conceptualize the film, that just became an obvious element to explore. [And generally the film] took us a while to edit because it was important to ensure that that balance stayed the way I had envisioned it from day one, which was to largely be making a film about Adrienne and Adrienne’s life, but the reality is you can’t make a biographical film about somebody’s life without covering their death, and you can’t cover their death unless you cover all aspects of it, which includes the first few days when the narrative was that she had killed herself and what happened to change that narrative. The interview itself with him in prison was motivated by two things: A, to find out the truth, but B, to humanize her for him so that he really understood the life that he took, and making sure that in the short window of time that we were going to devote to that particular moment that we captured the essence of those two elements because that was the point of seeing him.

This must be quite a weight off your shoulders. What was the recent premiere like for you at DOC NYC?

DOC NYC was great. The people there were amazing. They loved the film. It was great to have a local audience see the film, so that was a very positive experience and the festival for us wasn’t about getting distribution because we are with HBO, but it was really more about just getting that first initial look out to audiences and have them see it finally after years of production. And to be where we are now, [a few] days out from our HBO premiere, it’s bittersweet. It’s hard for me to use the word excited. I mean, people say, “Are you excited?” This is a film I wish I never had to make. You probably don’t hear that very often. I’m probably one of the only filmmakers out there who literally wishes their film didn’t exist. For me, it’s truly about serving the original mission and vision, which is to get people to know who Adrienne was, to get them to fall in love with her, to get them to mourn her loss the way we do, and now that they know her to go back and look at her work and see her movies that they didn’t see before and discover her as an artist. In that sense, I am excited that she will be out in the world, and that’s very important to me.

Before this interview, I looked up all the filmmakers that have been supported through the Adrienne Shelly Foundation since it was established following her death, which has become a remarkable part of her legacy. What’s it like for you to look back on that, having helped set it up?

I appreciate you asking that because that really demonstrates the whole purpose of the foundation. In 2008, which was a year after we started, Cynthia Wade, one of our early grant recipients, won an Academy Award for her short film “Freeheld,” so I knew within a very short amount of time that we were going to have impact. And whether it’s Dee Rees or Sara Colangelo, or Chloe Zhao, who we gave her a production grant when she was still making short films and won the Academy Award for Best Director this year, it is mind blowing to me. And it is I think the best honor and tribute I could have helped create for Adrienne is to help other female filmmakers in her name.

“Adrienne” airs on December 1st on HBO at 8 pm and will stream on HBO Max thereafter.