“Simultaneously magical and unfair,” is how Paul Rudd describes the night his friend Adrienne Shelly’s Waitress debuted to acclaim at the Sundance Film Festival in 2007. Less than three months before this triumphant moment, the director was found dead by her husband, Andy Ostroy, in the bathroom of her office. The scene had been staged to look like suicide, but when pressed to investigate, the police found evidence proving homicide and apprehended the culprit.

Now, 15 years later, Ostroy’s grief is still palpable and his directorial debut explores Shelly’s career trajectory from indie ingenue to a name lit up on a Broadway marquee. It is a bittersweet success story running in tandem with the tragedy casting a shadow over the filmmakers’ legacy – and the loved ones she left behind.

Candid conversations with family (including Shelly’s now 17-year-old daughter Sophie), friends and colleagues are entwined with archival footage, home movies, journal entries, and additional clips of Shelly’s work that punctuates this loss with questions of what could have been. It is a deeply personal documentary depicting Shelly’s bright life (as well as her career struggles) and the raw emotions describing this loss will have you reaching for the tissues.

There is no space between director and subject, which is a benefit when capturing the memoir-like aspects of major milestones. However, the close proximity of the director to the violent crime is occasionally detrimental to the final film. Two dominant threads take hold early on and elements leaning toward the true crime narrative occasionally threaten to overwhelm the woman at the heart of the story – a later interaction is unflinching and uncomfortable.

Perhaps some of the discomforts felt watching the thornier moments are a reflection of how unfathomable this tragedy is and the lack of a roadmap for grieving a senseless death. An intimate and deeply familiar discussion of her legacy is born out of Shelly’s relationship with Ostroy and the warmth emanating from the interview subjects. No doubt, the light he shines on her work will encourage viewers to explore Shelly’s back catalogue.

A wealth of options include Hal Hartley’s indie classics The Unbelievable Truth and Trust, as well as the material Shelly wrote, directed and starred in. Even if you aren’t familiar beyond the Keri Russell starring Waitress, you will come away from Adrienne with a sense of who the filmmaker was and could have become.

Humour and sorrow are inextricably linked in Shelly’s writing, and similarly, contradicting themes persist in this documentary. The joy of Waitress becoming a Tony-nominated musical is coupled with a profound sadness that Broadway audience members have never even heard of Adrienne Shelly, or that she struggled as a filmmaker before her biggest hit occurred posthumously.

Outside of personal relationships, the documentary is at its best when it captures how prolific Shelly was as she noodled with ideas; clips from an abandoned documentary on the theme of happiness are hilarious and heartbreaking.

Ostroy briefly discusses the need to “spin some gold” from this “horrifying negative” with the creation of the Adrienne Shelly Foundation to support women filmmakers and more time in the documentary dedicated to this endeavour would have been beneficial. The number of projects left unfinished and unrealised cannot be measured and this contribution to the arts is a fitting and affecting tribute.