Lilith Fair: The story behind the iconic ’90s music festival

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By News Room 9 Min Read

Lilith Fair didn’t necessarily start as a movement. 

It was originally just a talented young musician from Halifax — a self-described “good Canadian girl” — wanting to perform with other women like her.

It was the 1990s, and singer-songwriter Sarah McLachlan was releasing albums, scaling the charts and touring the country.

She remembers thinking, “I feel lonely. This is a weird job, and it would be so nice to connect with other women who are doing a similar thing to me.”

“But that’s when promoters started saying, ‘You can’t do this.… You can’t put two women on the same bill. People won’t come,'” she said. 

Then, as now, the music industry was largely run by men, and they treated female artists differently.

McLachlan ignored the promoters and, in 1996, brought Paula Cole on tour as her opening act. It went so well McLachlan decided to organize a festival that featured women-led bands and solo female artists.

Drawing on more than 600 hours of archival footage, the new documentary Lilith Fair: Building a Mystery tells the story of the groundbreaking concert tour. 

Lilith Fair ultimately changed the music industry and the lives and careers of many performers. It featured artists at the top of their game and future superstars, including Sheryl Crow, Tracy Chapman, Bonnie Raitt, Erykah Badu, Fiona Apple, Missy Elliott, Nelly Furtado, Jewel, Queen Latifah and Christina Aguilera. 

A group finale with Diana Krall, Sarah McLachlan, Angélique Kidjo, Lisa Loeb, Sam Bettens and Tara MacLean at Lilith Fair in 1998. (Crystal Heald)

In the documentary, concertgoers gush about how the festival changed their lives. It celebrated women, brought people together and created a safe space for women and queer people. It was a cultural awakening. 

But not everyone saw it that way. Even though Lilith Fair was the top-grossing festival of 1997, it was a pop culture punchline, dubbed “Vulvapalooza” and “Chickapalooza,” and the butt of jokes on late-night talk shows. 

The music industry pitted women against each other  

The larger context of the 1990s was “straight-up toxic,” McLachlan said in the documentary. 

Footage from that time is hard to watch: late-night hosts quipping about “fat chicks” and shock jocks joking about getting a boner. In an interview, a 19-year-old Jewel was met with an allusion to her performing a sex act; another time, a male host introduced her with a comment about her breasts. 

Photograph of singer-songwriter Jewel.
Playing Lilith Fair had a huge impact on the career of the singer-songwriter Jewel. “Everybody was doing well on that lineup,” she said. “We were having massive hits. I went from selling zero records in three years to selling a million albums every month.” (Lilith Movie Canada)

“That was a very ’90s ethos,” Jewel said in the documentary. “The predominant movement at the time was shock jocks.”

And when advocating for airtime on the radio, women were treated like a niche category — they were pitted against each other, competing for the same few spots regardless of their genre.

McLachlan remembers programmers saying one of her songs was great, but they’d already picked up something from Tracy Chapman or a new release from Jewel.

“And I was like, ‘And what’s that got to do with me?'” McLachlan said. 

“Those are all very different artists than me, but we all kind of got lumped into the same category.… They said women were not supposed to be played back to back on the radio: ‘It’s too much — people will change the channel.’ It just never made any sense to me.”

Lilith Fair: Building a Mystery | Trailer

The untold story of the groundbreaking all-women music festival, started by singer-songwriter Sarah McLachlan in the late 1990s.

Skepticism, controversies and change 

Lilith Fair launched in 1997. “I remember the first show at the Gorge,” McLachlan said. “Promoters were saying, ‘People won’t come. People won’t buy those tickets.”.

The show sold out — 15,000 people showed up.

But even with a strong start, there was skepticism and resistance, and it was a struggle to get sponsors on board. 

“I remember specifically one conversation with the water company, and they were like, ‘No, we’re kind of really focusing on a male audience,'” McLachlan’s agent, Marty Diamond, said in the documentary. 

“And I was like, ‘It’s water.'”

There were controversies too. 

Giving Planned Parenthood booths at the festival drew anti-abortion protesters and even bomb threats. But McLachlan and other performers were adamant that the sexual and reproductive health-care organization remain.

And facing criticism over the lack of diversity in their lineups — the festival was dubbed “Lily-White Fair” — organizers brought in more R&B acts. 

McLachlan admitted her mistakes. “We’re growing and learning as we go,” she said. “They’re all valuable lessons, you know, that enable us to get better.”

Erykah Badu joined the tour in 1998. She was one of many who brought her baby to shows, and every night, she joined the group encore, which she described as a village of strong women “putting a period at the end of a sentence.” And to this day, she maintains the tour vastly expanded her audience.

“People who would not get to hear of an ‘Erykah Badu’ or listen to even my type of genre of music were exposed to it,” Badu said in the doc. “My welcome into the industry was by Sarah McLachlan and Bonnie Raitt.”

In the end, more than 1.5 million people attended Lilith Fair between 1997 and 1999. 

No egos, no hierarchy — and no equivalent today

The skepticism for Lilith Fair seems almost absurd in 2025. But that’s because it fundamentally changed people’s presumptions about how audiences would connect with female musicians.  

Still, Lilith Fair remains unique. Female artists were the focus, and promoting women extended to the crew: they set up stages and equipment and worked as sound engineers. 

Photograph of the 1999 Lilith Fair crew.
The 1999 Lilith Fair crew photo. “We were the first tour to bring in extended health care,” road manager Dan Fraser said. “And these grown men would be crying because they could send their kids to the dentist.” (Lilith Movie Canada)

Crow called it a “communal” gathering and said the camaraderie backstage was rare.

“I mean, the Lilith tour was full of rock stars,” Crow said in the film. “But that feminine energy, I think, usurped the ego. There was no separation between artists. Nobody was more important than anybody else.”

Sheryl Crow and Sarah McLachlan rehearse backstage at Lilith Fair.
Sheryl Crow and Sarah McLachlan rehearse backstage at Lilith Fair. (Lilith Movie Canada)

As younger generations stumble upon the festival, it can still feel surprising. 

Grammy winner and Billboard Woman of the Year Olivia Rodrigo, for one, hadn’t heard of the tour and female singer-songwriters from the ’90s are one of her biggest sources of inspiration. 

“I remember someone bringing [Lilith Fair] up a few years ago and doing research on it and finding out that all of my favourite artists had played at this event — somebody like Sarah McLachlan and Sheryl Crow, Pat Benatar, Fiona Apple, Jewel and all these people that I’ve spent my whole life just adoring,”  she said in the documentary. 

“I was in disbelief that I’d never heard of it before.”

Watch Lilith Fair: Building a Mystery on CBC Gem and the CBC Docs YouTube channel.

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