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‘Adrienne’ Director Andy Ostroy on What Adrienne Shelly Left Behind

They called her a “unicorn.” Those who loved her best say Adrienne Levine, known by the stage name Adrienne Shelly, had the sort of Hollywood magnetism that borders on mythical. She was a little quirky, intrinsically bold, an artist shaped and haunted by the pursuit of joy. “I had never met anybody like her,” says her husband, Andy Ostroy, 15 years after her unfathomable death. Even now, he struggles to describe what he first noticed about her; it wasn’t that she was an indie film ingénue or a stunning strawberry blonde who stood all of 5’1”. “She was just this sweet little Jewish girl from Long Island,” Ostroy says. “That’s what I knew.”

The actress who’d adorned magazine covers in the wake of her films Trust, The Unbelievable Truth, and Serious Moonlight is the subject of Ostroy’s new HBO documentary, Adrienne, a heart-wrenching eulogy in film form. Today, Shelly is perhaps most applauded for her work writing, directing and acting in the Keri Russell-led Waitress, in which Russell’s Jenna, a waitress at a Southern diner, discovers she’s pregnant with her abusive husband’s baby and starts an affair with her OBGYN. Jenna is flanked throughout the film by her two best friends and fellow waitresses, Becky (Cheryl Hines) and Dawn (Shelly), each with their own oddball traumas. Such is an unusual concoction for a romantic comedy, and yet, even years after the first time I watched Waitress in a drafty hotel room, I can’t remember a film that made me feel so warm. The story became a Sundance darling and, eventually, a smash-hit Broadway musical starring Sara Bareilles. Shelly orchestrated the spectacle, but lived to see none of the flash.

On November 1, 2006, she was found dead in the shower of her West Village office, discovered there by her husband after she’d gone hours without answering his calls. Ostroy refused to believe Shelly had committed suicide; in the final days of her life, she’d been radiant with happiness, perhaps for one of the first times since her childhood, chiefly due to her young daughter, Sophie. His grief narrowed into tunnel vision, Ostroy pleaded with the detective’s office to investigate Shelly’s death as a murder. Sure enough, a suspect emerged: Diego Pillco, an Ecuadorian teenager who’d tried to rob the actress to pay off his debts.

While Adrienne gives plenty of weight to this murder mystery—and treats it as such—the true power of the film lies with all that came after. Much of the documentary focuses on Ostroy’s hard-fought battle with grief, and most poignantly, the grace he’s given his daughter. Sophie, by now a teenager, can’t remember her early years with her mother, yet her mother’s legacy touches everything she does. Even if she wanted to, she can’t escape Adrienne’s influence. She doesn’t know how to process this dual absence and presence. As such, she struggles to grieve; at one point, she tells Ostroy that she never cries.

But where Adrienne triumphs is in its refusal to sugarcoat the drudgery of healing. Nor does it paint broad strokes over Shelly’s own multi-faceted life. We see her pain as well as her exuberance. We see her failures and her triumphs. We see her grief. And by the end, miraculously, we see it reflected in Sophie.

In an attempt to understand just how much energy had to be fueled into such an intimate project, ELLE.com sat down with Ostroy to discuss Adrienne, both the film and the woman herself.

andy ostroy and adrienne shelly

Ostroy with Shelly.

Andy Ostroy/HBO

Was it always your intention to make a documentary about your wife? Or did this idea only materialize recently?

I had been writing a book for years, and it was a process that was taking a while. Then I took Adrienne’s mother to see Waitress The Musical, and she got to talking with a few out-of-town women sitting behind us before the curtain went up. Eventually, she shared that her daughter was the reason we’re all here, and she told them her name and one of the women said, “Oh, that’s great. Is she here tonight?”

And it got me thinking. I started looking around this packed theater of about 1,100 people, and I wondered how many of them know who Adrienne is, and that was the moment where I realized, not only do I need to tell the world who Adrienne is, but I need to make a film. She was a filmmaker. That’s the best way to honor her. And it immediately felt like that’s the obvious thing to do. So I put the book down and started to conceptualize the film and put the pieces together.

And how long did it take you to get to this final product?

From concept to now, three-and-a-half to four years.

How did you know you were the one who should helm this project, as opposed to having another filmmaker come in?

Well, there’s two answers. Number one, I’m a control freak. But, in all seriousness, when you have a story that is so deeply personal and has various elements that are biographical, true crime, the human interest aftermath part, you know—I just felt that no one can tell this story the way I want it to be told, and the only way to control the narrative so that it wouldn’t become a sensational crime film, or it wouldn’t become all biographical, was [to do it myself].

The found footage you weave throughout the film, had you seen most of it before? Or were there clips you hadn’t touched since Adrienne’s death?

I’d seen some of the films that Adrienne acted in. I saw the films she wrote and directed, but I hardly ever saw any of the archival stuff of her just as a person. I had tapes that were just staring at me up on my shelf for years. Until I decided to make a film, I really didn’t… There was no point to go through them. I figured, someday, when my daughter’s older, we’ll digitize them and sit down together, whatever, but when I decided to make the film, I did digitize those, and what I found was incredible. There were things in there from her 30th birthday to her 34th birthday, to these happiness documentary footage interviews. There was just incredible things that gave me the goal that I was looking for, in an archival sense, to bring this story to life.

Was your daughter on board with this project from the very beginning?

Yeah. She was a very active part of the filmmaking process. She was on a lot of the interviews. She’s credited three times. She did behind the scenes photography, additional camera. She was a PA. And I think, for her, it was really a way for her to truly understand not just who her mother was, but what her mother did.

What would you say you most want to come out of this documentary? You wanted people to know who Adrienne is, of course; that was the impetus. But now that you have the final product, what is it you want to see happen?

Well, there’s a primary and a secondary goal that I have. The first is what I set out to achieve, which is to, in a sense, bring Adrienne back to life. To have people get to know her, to like her, to fall in love with her, to mourn her loss, and to appreciate her as an artist, and to the point where they might want to now go and explore her body of work and see her films that perhaps they hadn’t seen before. The secondary is the film was always intended to be a gift to my daughter.

I think it’s the greatest gift I can ever give her, that she will have for the rest of her life as she emotionally develops and can see it in different ways as she gets older and matures.

Good documentaries move people and could maybe even change people and change the way they live. There are, I think, lessons to be learned from this film; that you can fight for someone. You can be heard. There are ways of dealing with grief. There are ways of dealing with grief when it’s a child involved. How do you tell a young child about death and murder? And if there’s just one person out there who watches this film and does something different because of what they took away from the film, I think that’s what a good documentary should do.

How did you work to balance the two narrative threads of this film: The tremendous radiance of Adrienne’s life and the grief and perseverance of you and your daughter’s lives in the wake of her absence?

When I first thought of making a film about her, there were three questions that needed to be answered. The first one was, who was Adrienne Shelly? The second one was, what really happened the day she died? And the third was, how does a family navigate the unthinkable? I didn’t really approach this film as a filmmaker. And it was easy for me to do that because I wasn’t a filmmaker. My fallback was as a viewer. What would I want to see? I wouldn’t want to see just a biography or just this or just that. I like a full, rich film. Especially when it’s a documentary.

So all those parts were important, but they didn’t get equal treatment. There’s so much going on and you’re bouncing back and forth, and that’s the inherent risk when you have multiple themes. There’s a lot of documentaries that are almost purely biographical, and there were times where I wish maybe that’s the movie I should have made. But I didn’t want to make that movie because I know what it was like for our family to experience this. I felt it would be a much richer movie—and also have greater value to the people who are watching it—because grief is universal. Death is universal. We all experience death. Every family has death. Every family experiences grief, and every family grapples with the concept of closure, which I touched on a little bit in the film. Closure is a concept I don’t really understand well because, to me, it’s like, “Okay, there’s stage one, two, three, four, five.” And then it’s, “Okay, let’s pop open the champagne because we’re done.”

Grief is never done. Fifty years from now, when you look back on the people who died in your family, it’s [still] raw. So, I think the trick was to try to get that right balance [in the film]. And I believe we have.

adrienne shelly in 1991

Shelly in 1991.

New York Daily News ArchiveGetty Images

So much of the film is also about Adrienne’s work, and how it’s taken on a life of its own in the years since her death. Do you have a personal favorite film from her repertoire?

I mean, I have to say Waitress. Being with her for five years, I watched her evolve during that period. When I watched Sudden Manhattan, I thought, “Okay, this is funny at times, and it’s crazy, but it’s her first film.” And then when I saw I’ll Take You There, I was like, “Oh, she’s starting to get more mainstream in her humor and subject material.” But still keeping the same kind of offbeat charm. But with Waitress, it… You know. I mean, we had discussions where she would say to me, “People always tell me to write something commercial.” And she would say, “That’s not how I write. I don’t write commercial. I write what I write.”

The irony is—and sadly, she never lived to see the success of it—she wrote this little movie that had this incredible commercial appeal and went on to be a huge box office success, and 10 years later, a smash historically successful Broadway musical and, you know, it is just…She was just doing what she did.

I’d be remiss not to ask you about the incredibly moving scene in which you finally meet with Diego Pillco. How did that materialize? Did you always want to meet him? Did you always want that meeting filmed?

I always knew I would [meet him]. I needed to meet him and talk with him—because he lied at his confession when he was arrested, he lied at his sentencing, and just the way I’m wired, I need to know the truth. I’m not one of those people that can just be, “You know what? It is what it is. Who cares? What does it matter what happened that day?” At times, I wish I was that person, but I’m not. My degree was in journalism. I’m wired to ask questions and find out stuff, and so I knew that someday I would go, but when I started to think about making the film, it became an obvious element of the film. He is one of two people who knew what happened that day, and he’s the only one that’s alive to tell it.

If you don’t mind me asking, what is it like for you now, watching that scene?

I’m just taken out of it. I don’t… It was so emotional for me to be there when he left. I mean, you see me break down because it was like I had put up a dam for those 90 minutes with him. I feel like I had a mission I was on. I achieved the mission. I left half of my guts on the floor in that room, and when I left, it was tied up with a nice little bow.

I don’t really think about it or him. And when I watch it, that’s what goes through my head is just like, okay, that’s what we did that day.

When you watched the full finalized version of the film, what was your reaction? What was Sophie’s?

I feel like the film is exactly, 100-percent what I set out to achieve. I don’t look at anything in that film and think, Damn, I wish I would’ve done…It’s literally the perfect execution of what I envisioned.

As far as my daughter goes, when she saw the almost final cut, she got very emotional and she said, “Dad, it’s great. I’m proud of you.” You know that teenagers don’t often offer praise. They don’t often just start talking to you, especially about emotional stuff, so it was a really amazing moment between us. It’s very bittersweet for everyone, but in particular for her. Looking at it through the eyes of a 17-year-old girl who lost her mother at an age where she now has no recollection of her, it has to be incredibly, emotionally bittersweet, but I know she appreciates that her mother, for those 99 minutes, is back, and the world sees her and the world appreciates her and the world loves her, and I do believe that as she develops into an adult, she’ll appreciate all that even more.

Is there any one scene from the film that you treasure most?

I think the ultimate favorite scene is when Sophie has her moment at the end when she cries, because we…we’re with her on her emotional journey. She starts off [at the beginning of the film] saying, “I don’t show my emotion. I can’t show emotion. I haven’t cried in years. I need to show emotion. It’s not healthy not to show emotion.” And then we see her let go.

I truly believe, in my heart of hearts, that unless that camera was in front of her, I, as her parent, wouldn’t have gotten her to that place.

This interview was edited and condensed for clarity.

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