In the 25 years since its final concert, the sheer groundbreaking force of Lilith Fair has been largely forgotten – even by those who were lucky enough to attend a tour stop of the all-female travelling music festival. What it meant for women in the industry – both on stage and behind the scenes – and for fans of any gender has been diminished over the years as well. With Taylor Swift, Ariana Grande, and other female artists routinely breaking records and making headlines, it may be hard for some to remember a time when seeing women topping the charts, touring together, or making millions off of merch wasn’t an everyday occurrence. Ally Pankiw’s new documentary, Lilith Fair: Building a Mystery, seeks to rectify that and place it firmly where it belongs in the pantheon of music history.

To begin with, Pankiw takes us back to 1996, when feminism was a dirty word in most corners of the industry and in the world (and really, that hasn’t changed as much as we like to think it has). At the time, radio stations and their music programmers would refuse to play two female artists back-to-back because the prevailing ‘wisdom’ was that listeners would be put off and change the channel. Concerts and festival bills were often restricted to one woman performer, because any more than that and someone might start to question the heteronormativity of the whole damn thing. Heaven forfend. All the major promoters were men, too, so the actual phenomenal, varied talent on offer was often overlooked if the woman artist wasn’t skinny enough or didn’t have large enough breasts. It almost sounds like a parody when the doc outlines just how many ways women were set up to fail in music, but that was the reality at the time.

So, when Sarah McLachlan faced backlash from within the industry for suggesting Paula Cole as her opening act for her next tour, it got her thinking. Not only were all women experiencing the same industry pushback, but it also meant that they might be open to banding together to fight back and prove that not only could you have two women on a bill and make it a success, but that you could have only women perform. People would want to see it happen.

And see it they did. In droves. Lilith Fair didn’t just happen; it was a bona fide hit across North America. Women showed up, but so did men. The musical acts that came on board for the first tour in 1997, excited to see women supporting women, included chart-toppers, Hall of Famers, and emerging artists. Even now, looking back, the performers have nothing but positive things to say about their fellow acts. That’s not to say they were perfect at all times. Some cop to being standoffish, some to being unsure what the tour really was, but some remain in awe of who and what they saw on stage and the leadership they saw off it.

Though the focus remains mostly on the women and what they achieved for themselves and for fans — who, it turns out, were just fine with an all-women line-up — Pankiw makes sure to remind audiences that there was far more to Lilith Fair than artistic and box office success. The Festival offered health and dental benefit coverage to roadies and other workers — a first in the industry. They also partnered with local charities at each tour stop, donating millions to not-for-profit organizations each year. Though both are more common wth touring musicians and festivals now, it took someone taking that first step to make it a viable reality. Fans also felt that the tour stops were some of the first places where they were given the space to be their authentic selves. Archival footage shows many contemporary concert-goers praising the support of LGBTQIA+ individuals on stage and in the audience. Some laughingly still write off Lilith Fair as a ‘lesbian fest’, which is ridiculously ignorant on so many levels, but it is accurate to say it was a positive queer space at a time when they were few and far between.

For those of us who were there–in my case, third row centre at Molson Amphitheatre in Toronto on August 15, 1997–the documentary does an excellent job of putting you right back there. I could smell the suntan lotion, feel the summer heat, and hear the crowd. If you weren’t there, or weren’t even born yet, the film does a fine job of putting you in the right frame of mind and generating the proper atmosphere.

The director doesn’t skip over the controversies faced by the festival, either. The 1997 lineup was, quite rightly, criticized for its lack of diversity in both genres and performers, being termed the “Lily White Fair” by some press. Tracy Chapman was the only BIPOC artist on the main stage for its freshman year. The resulting tours involved a concerted effort to reach out to a wider range of musicians, resulting in a much more balanced bill – although even then, with room for improvement. Missy Elliott, Erykah Badu, Queen Latifah, Meshell Ndegeocello, Mýa, Monica, Des’ree, and a host of others joined at various tour stops. It was actually the first tour Elliott ever joined, and the footage of her performance reminds us all why she remains a total legend.

One particularly memorable moment comes when the acts reminisce about having Sinead O’Connor join them on tour. Her fresh energy and quips to the press were just what the long-serving members of the festival needed. Her perseverance in the industry, despite facing so much hardship and criticism, seemed to reinvigorate McLachlan and many others. Watching her lay into the chorus of “Babylon” in one city is nothing short of a religious experience. It’s also a huge reminder of what we lost when O’Connor left us in 2023.

In her direction, Pankiw doesn’t venture far from tried and true methods of documentary storytelling here, but that’s more than fine. This is a case where talking heads and archival footage are exactly what the doctor ordered to tell this story the way it needed to be said. Almost everyone who was involved in the ‘90s participated, from McLachlan, Cole, Badu, Sheryl Crow, Jewel, Emmylou Harris, and The Indigo Girls, to many more musicians, as well as managers, agents, and tech crew from backstage. Add in archival interviews and a dash of nostalgia, and Lilith Fair makes for a compelling look back.

But what effect did the festival really have? That part is a bit less clear, but more so because of the muddled times we’re living in, not due to any misstep from Pankiw. That it launched the careers or popularity of some major stars is without question, as is the fact that it proved female musicians were not just marketable individually, but collectively. It also came at a time when “girl power” was gaining real traction with youth, and it made championing women not just fashionable but the new norm. It also made it a bit (and just a bit, mind you) more acceptable for straight men to outwardly express admiration for female musicians.

Did it change the minds of those with industry power? Not as much. McLachlan, Cole, and Colvin prove this by relating that the Grammys asked them to perform a medley of their nominated songs in 1997, while the other male artists in their category retained their traditional solo slots. And with cases like P. Diddy and #MeToo, we know that abuse, misogyny and sexism continue to exist within the music industry, as it does everywhere else. But Lilith Fair didn’t set out to move every metaphorical mountain, just the ones it could reach. And it shifted them as far as any similar endeavour ever has.

But Pankiw doesn’t let it just rest there. Though perhaps a less obvious side of the documentary, there’s a warning to be had here, too. Suppose we forget what was fought for and achieved by these many performers. In that case, it may allow those insidious gender norms and obstacles to rise up again and prevent future generational talents from flourishing.

So though Lilith Fair is a fantastic stroll through the nostalgia of a certain place and time, it’s also a reminder that real progress is hard to come by and requires constant attention, leadership, buy-in, and support. So take a page from these ladies’ books, and make sure we keep moving forward and never back.

Lilith Fair: Building A Mystery screened at TIFF 2025. The documentary will be available to Canadians everywhere on CBC and CBC Gem starting with the premiere of The Passionate Eye, Wednesday, Sept. 17 at 8 p.m. ET.

Read Rachel West’s interview with director Ally Pankiw.

Head here to get all our That Shelf TIFF coverage.

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