Adrienne Shelly was a brilliant actress, screenwriter, director, and champion for women, who was on the precipice of great acclaim when her life was tragically cut short at age 40. Shelly, who had just completed filming the 2006 movieWaitress, which she wrote, directed, and starred in, was never able to witness the massive success it would become.
Shelly dropped out of college during her junior year to move to New York City and pursue acting. Soon after, she got her first big break when filmmaker Hal Hartley cast her in two of his movies,The Unbelievable Truth(1989), andTrust(1990), which were quick indie hits. In addition to several guest appearances on television and starring in over a dozen off-Broadway plays, Shelly began to move toward a career behind the camera. She wrote and directed the 1999 movieI’ll Take You There, starring theBrat Pack’s Ally Sheedy, which won several film festival awards.
Celebrating womanhoodand the complex reality of being a strong female voice in the world of filmmaking was immensely important to Shelly. Her desire to portray authentic, complicated, unique, and strong-willed women on screen is made clear through archival footage in her husband Andy Ostroy’s 2021 documentaryAdrienne, which acts as a loving tribute to the late sensation. The project not only details Shelly’s many accomplishments and celebrates her through interviews with loved ones and colleagues, but also explores feelings of deep grief as Ostroy confronts the man who killed his wife and shares intimate conversations with his daughter Sophie, regarding the loss of her mother when she was just a toddler.
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Waitress: From Indie Cult Film to Broadway Musical Sensation
Adrienne was pregnant with her daughter Sophie when she wrote the filmWaitress. In the documentary, Adrienne’s family and friends explain that she was interested inexploring the idea of motherhoodand how feelings of excitement and terror, love and uncertainty, can coexist.
The movie tells the story of a small-town diner waitress named Jenna, who finds herself unexpectedly pregnant by her abusive husband and then has an affair with her obstetrician. Jenna is known forcreating delicious pieswith punny names like “Life’s a Rocky Road Pie” or “Aren’t You Sweet Potato Pie,” and often breaks into sweet sad songs while baking them.Waitress, starring Keri Russell, Nathan Fillion, and Cheryl Hines, who were all interviewed for the documentary, went on to premiere at Sundance Film Festival in 2007 to great acclaim, and Shelly won several posthumous awards for her work.
From 2013 to 2015,Waitresswas adapted into a stage musical with the artist Sara Bareilles composing. The play celebrated an all-female production team in honor of Shelly, and debuted on Broadway in 2016. The project garnered wide critical acclaim and was nominated for four Tony awards, among a slew of others. In an especially poignant moment in theAdriennedocumentary, Ostroy stands in Times Square staring up at a massive billboard promotingWaitresson Broadway. He is both immensely proud of Shelly and pleased that more of the world will get to see her work, and also deeply saddened that she is not here to see its success for herself.
In aninterview with Forbes, Ostroy explained Shelly’s creative philosophy. He said, “Happy/sad defines her work, and it’s also how she defined her life.” Much like Shelly tried to convey through her own films, it’s impossible forAdrienneto separate the light from the darkness.
The Tragic Death of an Exceptional Woman
On July 06, 2025, Adrienne Shelly was found by her husband, hanging in the Midtown apartment that she used as an office. Police initially ruled her death a suicide, though Ostroy was convinced that wasn’t the case. He pushed law enforcement to look further, and they eventually discovered evidence that proved that Shelly was murdered. Footprints at the crime scene led investigators to a 19-year-old construction worker, Diego Pillco, who was working in the building. He confessed to killing Shelly when she caught him in the apartment trying to rob her and threatened to call the police, and then staged the scene to look like a suicide. Pillco pleaded guilty to Shelly’s murder and was sentenced to 25 years in prison without the possibility of parole.
As part of the documentary, Ostroy decided that he was ready to speak face-to-face with Pillco for the first time since the sentencing hearing, 15 years earlier. He traveled to the Coxsackie Correctional Facility where he spoke with Pillco through an interpreter. Ostroy said on camera that his desire was twofold: firstly, to learn exactly what transpired on the day his wife was murdered, and secondly, to show Pillco the beautiful wife, mother, daughter, sister, friend, and creative visionary that Adrienne was, so he would understand exactly what he took from the world. Ostroy showed pictures of Adrienne and her daughter Sophie to Pillco, who expressed remorse for his actions, though the grieving husband had no interest in forgiveness.
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Andy Ostroy Celebrates His Late Wife withAdrienne
Much of the public that has been so thrilled to see the Broadway musicalWaitressbecome a national sensation in the last few years doesn’t even realize that it’s based on a movie, let alone who the woman was behind it all. Ostroy wanted to fix that withAdrienne.
The documentary is more than just a celebration of this incredible force of a woman; it is also an exploration into grief and how a family heals after an unimaginable loss. Ostroy and Shelly’s daughter Sophie was just shy of three-years-old when her mother died. Ostroy had the foresight to write down all the conversations he had with Sophie as he tried to explain death to a toddler, and over the years, when the little girl asked questions about her mom. He depicted some of those conversations verbatim in animated sequences throughout the documentary, lending a painfully heartbreaking tone to the film at times. A now-teenaged Sophie is interviewed in the movie, whichOstroy told the Guardianwas very special to him. He said, “One of the beautiful parts of the film is that I had conversations with [Sophie] and got real emotion from her that I don’t think I would’ve gotten if there wasn’t a camera there.”
Shelly’s family also spoke about her love of performing and the dedication she showed to her creative endeavors from a young age. Her colleagues described her tenacity and work ethic, and the unique wonder it was to be on set with her. Ostroy’s voice-overs detailing the person Shelly was dripped with emotion and tie the whole film together.
Ultimately, this documentary is not only a vessel with which to give viewers a deeply personal look into this extraordinary woman and to help her live on, but at its core it is truly a love letter from Ostroy to Shelly; from Andy to Adrienne. Maybe most importantly, from Adrienne to the world.
