Adrienne Shelly's husband on revisiting her life and facing her killer in new documentary: 'I will never have closure'

Adrienne Shelly's life ended fifteen years ago on Nov. 1, 2006, when she was murdered in her West Village office. But her story continues in Adrienne, a moving documentary portrait of the late writer, director and actor crafted by her husband, Andy Ostroy. Premiering on HBO on Dec. 1, the film eschews a typical chronological structure, instead moving back and forth in time as it depicts Shelly's early career as a '90s indie film favorite, her shift into writing and directing her own projects (including the Sundance sensation, Waitress), her marriage to Ostroy and the family they created, and the sequence of events that followed his discovery of her body to New York City police apprehending her killer. Adrienne's approach makes its subject still feel present nearly two decades after her death.

According to Ostroy, that's a reflection of how Shelly exists for him. Speaking with Yahoo Entertainment, the widower says that he's never sought the kind of closure that some try to achieve after a devastating loss. "I will never have closure — It's impossible to have closure," he explains. "I admire people who believe they can lose somebody tragically and find closure. I aspire to that, but I cannot even conceptualize that. I don't understand the concept of closure or the five stages of grief, I've always wondered what happens when you're done with stage five. Does that mean, 'OK, I've moved on?' For me, life doesn't work that way."

Adrienne is representative of how Ostroy has navigated his own way through grief over the past fifteen years, and how he's sought to keep Shelly's memory alive for their daughter, Sophie, who was only two years old when her mother died. "What I've done in my life is to take her death and turn it into something positive. That's where making this documentary came from — trying to use her death in a way that has redeeming value. Otherwise, it's just a horrible death."

Ostroy confronts the disturbing details of his wife's murder head-on in the climax of the documentary when he sits down opposite Diego Pillco, the man who took her life. Pillco was 19 at the time of his fatal encounter with Shelly, and had recently arrived in New York from Ecuador, picking up odd jobs as a construction worker — and stealing money from the places where he worked — as he sought to pay off his debts.

As he recounts to Ostroy in the film, he was in the process of robbing Shelly's office when she discovered him and threatened to call the police. "I got behind her and covered her mouth and told her not to call the police," Pillco recounts through an interpreter. "I lost my mind... I was choking her with my hand at the same time I was covering her mouth so she wouldn't make noise. I took my hand off... and I saw that her lips were blue."

Pillco then hung Shelly's body in the office bathroom, where Ostroy discovered her hours later. Police investigators initially treated her death as a suicide case, but Ostory's repeated objections spurred a closer examination of the crime scene and ultimately put them on the path to Pillco's apartment door in Queens. Pilco pleaded guilty to first-degree manslaughter at his 2008 trial and received a 25-year prison sentence that will end in 2033.

Ostroy was in the courtroom when Pillco received his sentence in 2008 and remarks in the documentary that, at that point, 25 years seemed like a long time. But now — with only a little over a decade left until Pillco's release — he felt compelled to have his first face-to-face conversation with his wife's killer. "The film was always intended to be three parts: life, death and aftermath," he explains. "The part about her death was something I had always been needing to understand in more detail — what really happened the day she died. As I say in the movie, there's only one person alive who knows what happened and that was him."

"[The meeting] became part of the cinematic process of making the film," Ostroy continues. "It is a fairly climactic moment, at least in my life, in the last 15 years, so I felt it would be appropriate to tie into my other thoughts about where I — in addition to others in her family — have been left by this tragedy. I was there on a mission and I achieved that mission and put it in its proper time and place."

During their dramatic encounter, Ostroy listens quietly as Pillco explains what happened on Nov. 1, 2006, asking the occasional question to clarify events that he says Pillco lied about in previous accounts. When it's Ostroy's turn to speak, he presents Pillco with the last photographs of himself, Sophie and Shelly prior to her death, and then the Shelly-less family pictures that followed. "Adrienne missed a lot," he says through tears in the film. "This is what [Sophie] was left with: me, just me."

Over the years, Ostroy has notably pushed back against those voices — including former President Donald Trump — who might try to seize on his wife's death as an excuse to demonize illegal immigrants. "[Trump] uses murders like Adrienne's — though never hers specifically, fortunately — as political props," Ostroy wrote in a 2016 New York Times column. "It’s politically expedient for xenophobic agitators like Mr. Trump to scapegoat the millions of foreigners who have come to the United States in search of a better life. But his malevolence toward immigrants runs counter to the principles on which our great nation was founded."

At the same time, Adrienne makes it clear that he didn't go into this meeting looking for, or expecting to find, closure. Asked whether his attitude about Pillco has changed since his sentencing, he replies: "He's in the place he should be, in my head and in the minds of her family." And he's still wrestling with the question of how he'll feel when Pillco is released 12 years from now. "I think it's what anyone would feel: a sentence is never enough when someone killed somebody."

Ostroy also emphasizes that the parts of the film that deal with Shelly's death shouldn't overwhelm the passages that celebrate her life. "The point of making the film was to humanize her as more than just a victim of a murder: it's to show the world who she was." Since Ostroy met her in the early 2000s, after she had already moved one of the most popular indie movie ingenues of the '90s, he turned to her friends and collaborators — including director Hal Hartley — to help him understand who that version of Adrienne Shelly was.

"I met Adrienne Levine, this sweet Jewish girl from Long Island," Ostroy says. "I didn't meet Adrienne Shelly, indie darling. I only knew the normal, real person who decided that she needed something different in her life. We came together at the right time, and that's what made it great. We had worked out so much of our s*** before that, so we were ready to be together, have a child together and be a family."

One of the '90s stories that Hartley tells Ostroy in the film involves his and Shelly's breakout film, Trust, which was picked up by Miramax when Harvey Weinstein still ran the label. According to Hartley, Weinstein wanted him to recut the film to add a nude scene with Shelly. "I didn't really know much about that stuff until I sat with Hal," Ostroy says. "I had heard little snippets from her, but the thing that made Adrienne so special is that she was just a positive person, and she chose to dwell on that which she could control rather than stuff that may have happened to her that was unpleasant."

But Ostroy also says that Shelly would be encouraged by the #MeToo movement that eventually toppled Weinstein, along with other toxic men in the film industry. "I think she would be like, 'Finally — this is the kind of stuff I've been writing about for years.' She was writing about women being abused and objectified and harassed when it was just life experience, and which she partly experienced herself on sets here and there. So she would be very deeply gratified to see it being at the forefront of our culture today."

As he tracked his wife's career over the course of making Adrienne, Ostroy says that he also witnessed "the maturing of an artist," and believes her best work lay ahead of her. "Her execution was so much more precise with Waitress, and when I look at that film, I think it would have launched her career into the stratosphere. That's the ultimate tragedy of her death from a professional standpoint: she would've been one of our great voices today as a writer and director."

Perhaps it will be her daughter who continues Shelly's creative legacy. Ostroy says that their now-teenage daughter has dabbled in filmmaking herself. "She's in a film class in high school, and makes short films," he says, with pride. "But when she talks about her career, she also talks about social work and helping people. I just want her to do whatever she wants that will make her happy, and feel like she's contributing into this world. So whether that's being a social worker or a filmmaker, then that's what we'll support. I always felt this film would be the greatest gift I could give Sophie as she develops into adulthood and reflects back on who her mother is and how she can and will be a big presence for her."

Adrienne premieres Dec. 1 on HBO and HBO Max