Affirmation Across the Generations
'Lilith Fair: Building a Mystery' by Canadian filmmaker Ally Pankiw is a rallying call for change inspired by Sarah McLachlan and her successful all-women music festival
“Sarah McLachlan is my new icon.”
So says my 19-year-old daughter as she stands, clapping enthusiastically, from our seats on the first balcony of Toronto’s Roy Thomson Hall as Lilith Fair: Building A Mystery director Ally Pankiw takes centre stage.
Her documentary about a twentysomething Sarah McLachlan and her dream to create an all-women touring music festival in the late 90s had its world premiere as the Toronto International Film Festival’s (TIFF) final gala on Saturday, September 13th, 2025.
It premieres tonight (Sept. 17th) on CBC at 9 pm AST/8 pm EST and will be streaming on CBC Gem. Its international launch is scheduled for Sept. 21st on Disney+ and Hulu.
The film is both a nostalgic trip back in time and an inspiring story for those who seek to be heard today.
Pankiw straddles both worlds.
She was a young kid in Alberta when Lilith Fair existed, but she knew the stories of the women-only tour with artists such as Bonnie Raitt, Jewel, Erykah Badu, Deborah Cox, The Indigo Girls, and Tracy Chapman – and the feeling of being in a safe place, where you could be yourself and feel joy with friends. No fear of the ‘accidental’ boob brush-by or ass grab dancing in front of the Lilith Fair stage.
Today, as a Canadian filmmaker negotiating a career path through Hollywood, Pankiw is equally in awe of what McLachlan accomplished off-stage, building a financially successful all-women touring music festival in the face of derision and public ridicule from the men who controlled the music and media industries in the 1990s.
Lilith Fair: Building a Mystery moves back and forth, showing both sides: the public adoration of thousands of fans belting out '90s hits, and the musicians’ grimaces and side eyes during cringey press conferences.
There’s also plenty of interviews with Raitt, Badu, Jewel, Paula Cole, Joan Osborne, Amy Ray and Emily Saliers of The Indigo Girls and many others, including archival interviews with the late Sinead O’Connor.
For me, it was a walk down memory lane; for my daughter, it was a revelation.
Young women leading, being creative, flipping the bird and calling bullshit on anyone telling them otherwise.
Affirmation across the generations.
In one particularly jarring juxtaposition, Sheryl Crowe leaves the Lilith Fair tour to appear at Woodstock 99, the now-notoriously noxious festival of machismo. While on stage, some guy down front yelled ‘show us your tits!’ and Sheryl did what most women do when confronted with an asshole; she laughed it off and kept playing.
Looking back on it during her interview in the documentary, Crowe smiles ruefully and says that afterwards she ran back into the warmth and comfort of McLachlan’s arms – because that’s what girlfriends do.
Talking to my daughter after the screening, she said she was well aware of Woodstock and its reputation – and was completely ignorant of Lilith Fair and its female-centric beauty.
“No one has heard of Lilith Fair, Mom,” she said. “No. One.”
A statement I found both surprising and depressing, considering the prominent place Lilith Fair holds in my cultural memory.
While I never attended Lilith Fair, it toured from '97 to ’99, which were my first years in New Brunswick, I certainly followed it, reading all the coverage that left me feeling...conflicted.
I loved Sarah McLachlan, had all her albums, but had she created some airy New Agey chick fest, as the late-night hosts and SNL gags suggested? In punching back, these women had become the punch line.
Watching and listening to artist after artist sing their hits as I mouthed the words silently to myself, I felt nostalgic, and a bit guilty that I hadn’t done, I don’t know, something, anything, to carry the memory of Lilith Fair forward.
To Pankiw’s credit, she tackles that feeling by exploring why Lilith Fair has faded from view and what can be done to bring it back, not just its memory, but its spirit too.
Sitting on stage for the post-screening Q&A, McLaughlin was enthusiastic in her praise of Pankiw’s film and the feelings it inspires.
“I want to bring it back,” said McLachlan to wildly enthusiastic applause. “Damn it.”
However, McLachlan says it's not for her to do that.
“It needs to be championed by a younger artist.”
Regardless of whether the festival itself returns, McLachlan noted that the Lilith Fair spirit reverberates today through the dominance of women artists on the charts and their support for one another.
There’s Beyoncé, Lady Gaga, SZA, Chappell Roan, Sabrina Carpenter, Taylor Swift, and Olivia Rodrigo, the latter appearing in the film to talk about the Lilith Fair artists and their influence on her.
This is my daughter’s cultural experience, being a fan of artists who create a safe bubble for her and her friends to feel joy and be themselves in the face of a world contracting.
Pankiw’s Lilith Fair: Building a Mystery has arrived at just the right moment to remind us that young women can and will change the world – whether the world wants it or not.
Our job is to cheer them on.
______
Lilith Fair: Building a Mystery is directed by Ally Pankiw and produced by Dan Levy and Christina Piovesan.
In Canada, you can watch it on CBC Gem.
Everywhere else (excluding Canada), you can watch it on Disney+.
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I absolutely loved the Lilith Fair documentary. Like you it left me wishing I had gone (ignoring the reality that we were raising 2 young kids and had no money at the time, haha). Great article. Thanks.