‘Lilith Fair: Building a Mystery’ Strikes a Timely Chord in These Exceedingly Hellish Times

"Big surprise: women and a diverse group of people built a better system," filmmaker Ally Pankiw told Jezebel.

By Audra Heinrichs | September 19, 2025 | 3:32pm

Photo: Getty Images Entertainment Movies

‘Lilith Fair: Building a Mystery’ Strikes a Timely Chord in These Exceedingly Hellish Times

Once upon a time, a Grammy-winning singer-songwriter convened a who’s who of her female and femme peers—from industry native to neophyte—for a special string of concerts in sprawling amphitheaters and sacred fields across the country. Perhaps you’ve heard of it. Maybe you, or someone you know, was even there.

For three summers, Sarah McLachlan’s brainchild, Lilith Fair, did the so-called impossible: established itself as a safe space for women and queer concert-goers, and became the top-grossing festival of the nineties. Now, it’s a supernova, the stuff of musical lore—hallowed by its headliners and attendees, and even more so by those who were too unlucky or too young to go. Filmmaker Ally Pankiw counts herself in the latter category.

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In Lilith Fair: Building a Mystery, which premiered at the Toronto International Film Festival (TIFF) on September 13 and will stream on Hulu and Disney+ on September 21, Pankiw pays homage to the house that McLachlan (and several others) built. Its origin unspools with the help of more than 600 hours of never-before-seen archival footage and photographs and several touching sit-downs not only with its stars, like The Indigo Girls, Sheryl Crow, Erykah Badu, and Paula Cole, but also with the people who worked tirelessly behind the scenes to make it happen, including McLachlan herself.

“Everyone wanted to talk about the special place I think that Lilith holds in their hearts, and how much of a little bubble of joy it was in a very bleak time for a lot of the demographics that Lilith spoke to,” Pankiw told Jezebel on a recent Zoom call.

In her words, the festival became its own “gorgeous ecosystem.” Backstage, there was no hierarchy. Babies were breastfed and passed around with glee, nightly jam sessions broke out on buses and in dressing rooms, and production crews were properly paid and given healthcare—a rarity for freelancers even now. In the audience, too, was a camaraderie that remains an anomaly at most corporate-backed festivals in the U.S., save for maybe All Things Go and Brandi Carlile’s Girls Just Wanna Weekend.

“It’s scary to people that hold power when women gain power, too,” Pankiw said. “I think sometimes it’s a sort of unconscious punitive pendulum swing. When a bunch of young women are getting what they want and making what they want, that’s a threat.”

At all participating venues, Lilith asked organizations like Lifebeat, RAINN, and the Breast Cancer Fund to set up booths. And at each stop, $1 from every ticket sold was donated to a local charity selected by the festival. Ultimately, Lilith raised over $10 million for women’s charities and local causes during its initial run from 1997 to 1999. In one particularly resonant clip, McLachlan is grilled by a journalist as to why anti-abortion groups weren’t given a table. Her answer: “It’s my festival. And I get to choose.”

As the story goes, the 28-year-old McLachlan was a success story in mid-’90s pop music, with Fumbling Towards Ecstasy, her third and most recent album, receiving a glowing reception. Yet, she was frustrated. The music industry was—as it sadly remains to be—largely dominated by men: radio jockeys who wouldn’t play two female artists back-to-back; event promoters convinced that more than one woman on a bill couldn’t sell; and nationally respected journalists who weren’t covering up-and-comers. Lilith was her solution.

“It’s this really interesting parallel to conversations that are happening right now in the entertainment industry,” Pankiw continued. “We’re in this weird contraction period, where it’s like people have forgotten that investing in women and diverse people is actually an opportunity, not a risk.”

Today, the festival is fondly remembered for inviting the likes of The Chicks, Queen Latifah, Fiona Apple, Tracy Chapman, and Sinead O’Connor, and has often been credited with springboarding the careers of Missy Elliott, Christina Aguilera, and a host of others. Still, it didn’t last. Lilith abruptly ended after 1999, and though there was a less successful revival in 2010, canceled performers and a reported lag in sales on the heels of the recession dashed hopes for a modern run.

Only, now, the music industry counts more socially and politically outspoken female and femme artists than ever—so it seems we’re standing on fertile ground for a revival? Why hasn’t there been another attempt? Corporate greed? Censorship? A lack of McLachlan-esque courage?

“I think it’s that no one’s taking it upon themselves to do it,” Pankiw said. “A lot of people would say yes. I think it’s just…there’s a lot of fear right now.”

At the time, Lilith served in stark contrast to its competitors on the road. During its last tour in the summer of 1999, the Woodstock revival became a breeding ground for both blatant and latent misogyny—and subsequently devolved into violence, rioting, arson, and sexual assault. After witnessing what transpired at Woodstock, Crow, who played both tours, told reporters: “I’m hoping it’s not representing our future as a nation, or the youth of America.” We now know that—spoiler alert—it was. As to why the music industry—and society writ large—continues to repeat these toxic cycles, Pankiw chalks that up to more fear.

“Big surprise: women and a diverse group of people built a better system,” Pankiw jested. “Like they always do, they built a more equitable festival that was actually fostering talent.”

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