Drew Burnett Gregory is back at TIFF, reporting with queer movie reviews from one of the world’s most prestigious film festivals. Follow along for her coverage of the best in LGBTQ+ cinema and beyond.
A couple weeks from now, a variety of artists will perform at the 2025 All Things Go music festival just outside DC and at a concurrent festival in New York. This year’s lineup includes Doechii, Lucy Dacus, Joy Oladokun, Clairo, and Kesha. In recent years, the festival has been affectionately dubbed Gaychella and Lesbopalooza, monikers that incite enthusiasm in the communities they represent. But almost 30 years ago, another lineup of artists was called Lesbopalooza in a different tone. When critics and industry insiders and random men who didn’t attend called Lilith Fair that same name, they did so with derision as a way to further ostracize and belittle its collection of female artists.
Lilith Fair: Building a Mystery, Ally Pankiw’s new documentary about Lilith Fair, begins in the present. It shows us young people on TikTok discussing or discovering this moment in recent music history. Then it cuts to Olivia Rodrigo talking about the importance of Lilith Fair and the influence of those artists on her own work. At first, it seems the documentary is trying to appeal to Gen Z first and foremost, as if its primary goal is to teach young people rather than be for those who already care about Lilith Fair, including attendees. Luckily, this isn’t the case. Bookending the film in the present instead functions as a way to underline the influence of those three years of music tours. There would be no Lesbopalooza (positive) without Lesbopalooza (negative).
Using a mix of archival footage and contemporary interviews — as well as some spoken excerpts from Sarah McLachlan’s tour diary — the film creates a portrait of Lilith Fair and the culture it fought against. It illustrates the sexism of the 90s music industry and shows how McLachlan refused its boundaries. First, she invites Paula Cole to be her opening act despite the industry standard that two women can’t be on the same bill. When that’s a success, she begins to imagine something bigger.
As someone born in 1993, I did not attend Lilith Fair, but I’ve long romanticized it. This film feeds into that romance. From the opening night at The Gorge to Indigo Girls creating camaraderie among the acts to the surprise success that became undeniable, the archival footage — of performances, of fans gushing — allows those of us who weren’t there a little taste of the magic. It also shows the power of the shows beyond their lineups: the money raised for charities, the focus on having women crew, and even the insistence of giving all the crew healthcare.
It also displays the cost of this rebellion. Like the wonderful Indigo Girls documentary from a couple years ago, It’s Only Life After All, we’re shown how quickly Lilith Fair and its associated acts became an easy punchline. Both that documentary and this one reveal how the jokes weren’t a lighthearted jest but a more sinister reinforcement of sexism and homophobia.
One of my favorite parts of the documentary invites music journalist Ann Powers to respond to the complaint that it was women critics who were harshest, women critics who seemed to always be discovering “women musicians” anew. Powers notes that she was often writing the pieces her male colleagues and bosses assigned her. The sexism of the music industry didn’t just impact the artists — it was also experienced by the women writing about them.
By the end of Lilith Fair’s three years, the exhaustion of everyone involved — especially McLachlan — is deeply felt. It was a resounding success and yet the ambitious tours combined with the cultural backlash including bomb threats from anti-abortion groups made it taxing. The final conclusion is a hopeful one: these tours had a greater impact than McLachlan and her collaborators could ever have imagined at the time. It also leaves room for a different, less simplistic kind of hope. Like the angry young white men at Woodstock ‘99 and the media eager to tear women down, many of society’s worst impulses continue on. But anyone can take up the mantle of Lilith Fair, to refuse discriminating practices and push to make our world a little better. We can work together and view our successes as intertwined rather than in competition. We can gather and make a new world, even if it only lasts a few years, a summer, a night.
Lilith Fair: Building a Mystery will be available to stream on Hulu and Disney+ starting September 21.
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