- Adrienne Shelly, who wrote, directed, and starred in “Waitress,” was killed in 2006 at age 40.
- The filmmaker wasn’t alive to see her movie’s success and subsequent musical adaptation.
- Her husband, Andy Ostroy, spoke to Insider about making a documentary to “bring Adrienne back to life.”
Andy Ostroy remembers the exact moment he decided to make a documentary about his wife, the filmmaker Adrienne Shelly, who was killed on November 1, 2006.
He was sitting in the audience of “Waitress” at the Brooks Atkinson Theater on Broadway listening to his mother-in-law explain to two strangers, using vague terms, that her daughter had something to do with the show.
“Oh, that’s great. Is she here tonight?” one of them asked.
It made Ostroy wonder how many of the 1,000-plus people who were about to watch the hit musical based on his wife’s movie actually knew Shelly’s story. At that moment, he decided to pause the book he was writing about their life together and make a film instead, so people could really see her.
Shelly was best known for writing, directing, and starring in the 2007 film “Waitress,” which began filming in December 2005. She submitted the film to the Sundance Film Festival the following year, but she was not alive to see it get accepted.
The filmmaker was killed on November 1, 2006. In February 2008, Diego Pillco pled guilty to entering the Greenwich Village apartment Shelly used as an office to rob her, strangling Shelly when she threatened to call the police, and then staging her death as a suicide. Pillco is currently serving 25 years in prison after being sentenced in 2008.
Released 15 years after Shelly’s death, Ostroy’s new HBO documentary, called “Adrienne,” sets out to tell Shelly’s story so that fans of “Waitress” remember more than just her name.
Insider spoke to Ostroy about the inspiration behind “Adrienne,” the film’s powerful portrayal of their daughter’s grief, and why it’s so important for him to help people understand the legacy Shelly left behind and what she stood for.
Shelly was married to Ostroy for over three years before her death
As much as “Adrienne” is a movie about Shelly, it’s also a movie about Shelly and Ostroy’s life together before it was cut short. The documentary covers their whirlwind romance — how the two met on Match.com in late 2001, got engaged in Paris the following summer, and married in December 2002.
She was an actor and filmmaker who had success in independent films like Hal Hartley’s “The Unbelievable Truth” and “Trust.” She wrote, directed, and starred in films like “Sudden Manhattan,” about a woman who witnesses two murders on the same street on two different days, and “I’ll Take You There,” which chronicles what happens when a woman tries to force a man to move on after his marriage fails.
As Shelly herself recounts in footage featured in “Adrienne,” the idea for her most commercially and critically successful film, “Waitress,” came to her while she was eight months pregnant with her daughter, Sophie, and “terrified” that becoming a mother would transform her into someone she didn’t recognize.
“The actual fear of how your life is going to change, it’s not spoken about,” Shelly says in the clip. “So, I wanted to write a movie about those fears and give those fears a voice.”
The movie “Waitress” follows Jenna Hunterson (Keri Russell), a small-town waitress at a diner with an almost-magical ability to make pies that help her express her emotions. She’s also pregnant with a child by her abusive husband, Earl (Jeremy Sisto), and dreams of saving up enough money to leave him and start a new life. Throughout her pregnancy, she struggles to love her baby while also starting up an affair with her doctor, Jim Pomatter (Nathan Fillion).
Shelly stars in the film as Dawn, Jenna’s quirky co-worker who supports her along with their friend and fellow waitress, Becky (Cheryl Hines).
“Waitress” was a hit from the time it premiered at Sundance and was well-received by critics and audiences in its wider theatrical release. But it is the musical adaptation that debuted on Broadway in 2016, with a book by Jessie Nelson and music and lyrics by singer-songwriter Sara Bareilles, that introduced the story to a whole new audience and gave it a life of its own.
Ostroy designed his documentary to ‘bring Adrienne back to life’
Ostroy said that he made “Adrienne” to keep his late wife’s spirit alive.
“The film was always designed to bring Adrienne back to life,” he told Insider, aware that some viewers are just being introduced to her but hoping they take away from it an understanding of how special she was. “Perhaps they can grieve her absence in some way the way we do.”
Ostroy structured the film to have three interwoven stories, called “life,” “death,” and “aftermath.”
To help him build a more complete picture of the filmmaker’s entire life and career — they’d only been together for five years before she was murdered — he recruited Shelly’s other family members and friends to help “fill in the blanks” about his wife’s life. “Her formative years both as a person and as an artist were unknown to me,” Ostroy said.
In conversations with Ostroy, Shelly’s loved ones explained the milestones in her life that impacted her the most, like the death of her father, Sheldon “Shelly” Levine, when she was young, her decision to drop out of school to move to New York and become an actor, and the fears she would express to them about being alone forever before she met Ostroy.
Another important point of the film was for Ostroy to demonstrate the impact Shelly’s films would have on the world. “She literally was #MeToo in many ways before #MeToo existed,” he told Insider, pointing to the “very strong feminist voice” in all her films.
“Almost in a very pioneering way,” he added.
One moment in “Adrienne” demonstrates this aspect of Shelly’s legacy in a darkly humorous way. Ostroy tells a story in the film about bringing Shelly’s ashes to the theater where “Waitress” was playing at Sundance so she could have “her moment” at the premiere.
“I remember throwing ashes in the air and Harvey Weinstein walked right by and they landed on his shoulders,” Ostroy says in the documentary. “And I just started laughing on the inside because literally, it was as if Adrienne was right next to me laughing and thinking that was the funniest thing ever.”
In addition to shedding light on an underappreciated filmmaker, ‘Adrienne’ is a stunning portrait of grief
Shelly and Ostroy’s daughter, Sophie, was only two years old when her mother was killed the day after Halloween in 2006. She’s a teenager in “Adrienne,” and Ostroy enlisted Sophie to narrate her mother’s life by reading journals found at Shelly’s childhood home.
She also voices her younger self in animated drawings featured in the documentary, which Ostroy used to depict his daughter’s journey with grief throughout her childhood. The voiceovers are based on real conversations about their grief the two had been privately having for years, all throughout Sophie’s life.
“Ever since Adrienne died, I would sit with Sophie, especially in the earlier years like at bedtime, and we would talk,” Ostroy told Insider, calling the conversations “fascinating.”
“I had a small Blackberry, and I just started typing verbatim these conversations because something told me that someday there will be a very meaningful point to having these, even if it was just nothing more than Sophie being able to look at a catalog of conversations and see her own development emotionally as she matured throughout this process,” he said.
In one particularly moving and raw moment in the film, Sophie sits down before bed one night to speak with Ostroy about grieving her mother, talking about how Halloween and Mother’s Day are her hardest days.
“I’m just jealous all day,” Sophie says about Mother’s Day, explaining that it’s because she realizes she’s “never” going to have the relationship with her mother that other daughters get to have with theirs. She admits that the “permanency” of that fact gets harder as she gets older.
But Shelly, Ostroy says, has left behind a bit of a roadmap for her daughter and her husband based on how she lived her life.
“I used to say that Adrienne was 5’1″, but she was a giant in her industry, and she stood tall when it came to fighting for what she believed in, to executing on her vision, and making sure that her very strong very unique voice is what ended up on screen,” said Ostroy, reflecting on her legacy.
He said in “Adrienne” that while he’s had moments of sitting on the floor crying and smelling her clothes, he was also quick to understand that he had a purpose — to make sure his daughter was okay and to learn the truth about the day of her murder. He bravely shared the latter journey on film.
Ostroy, who is not a filmmaker by trade, told Insider that he would invoke his wife whenever he hit a roadblock in making the documentary: “What would Adrienne do in this particular spot?”