“Almost everybody I knew didn’t know who Lilith was,” Sarah McLachlan says in archival footage in the new documentary, Lilith Fair: Building a Mystery, which premiered in the United States on Hulu Sept. 21. “She’s such a strong and wonderful feminist figure.

“In religious mythology, Lilith was Adam’s first wife, before Eve,” McLachlan explains. “She was created of the same stuff he was, yet he refused to treat her as an equal. So she said, ‘I’m out of here.’ Lilith left the Garden of Eden and built her own garden, dancing and singing among women who, like her, refused to surrender their strength.”

Guided by that resolve, McLachlan spearheaded the creation of Lilith Fair, the music festival of all women (or women-fronted bands) — a largely unprecedented endeavor to that point — that toured in 1997, 1998 and 1999, followed by a revival in 2010.

“This is a weird job,” McLachlan muses in the documentary of the tour’s origin. She recalls thinking, “It would be so nice to connect with other women who are doing a similar thing.

“Independently, we had fanbases. Together, I thought, ‘How could this fail?’ ”

McLachlan’s instincts proved right, as Lilith Fair stormed the United States and Canada. The 1997 run grossed $13.1 million and sold 489,000 tickets over 29 shows, as reported to Billboard Boxscore. The totals for 1998 swelled to $21.2 million and 646,000 tickets from 41 shows. For 1999, it pulled in $18.6 million and 482,00 tickets more than 34 shows. Lilith Fair — which also donated millions of dollars to charitable causes — finished among the top 20 tours in each of those years.

“It wasn’t until we hit the road that we really understood the magnitude of what we were trying to create,” Catherine Runnals, Lilith Fair production coordinator, says in the documentary. “By comparison, something like a Lollapalooza, they were doing 15 or 18 shows. We did four or five festival shows in a week. It was absolutely bonkers.”

In one of the film’s best lines, Runnals sums up, “It felt like we were building the airplane while we were already flying it.”

In celebration of the groundbreaking tour, Billboard has compiled The Biggest Hot 100 Hits by Acts Who Played Lilith Fair, a 100-song countdown — and Spotify playlist — commemorating the 100 top titles on the Billboard Hot 100 by acts who shone on the festival’s stages. Included are hits by three artists played all four iterations of Lilith Fair: McLachlan, Sheryl Crow and Suzanne Vega. The chart encompasses 17 No. 1s among 86 top 10s, with songs spanning 38 years, from Heart’s “Magic Man,” from 1976, through Idina Menzel’s “Let It Go,” from 2014. (The retrospective includes acts’ hits in lead roles, as well as featured billings in which the lead artist didn’t provide vocals.)

Among the 100 songs on the ranking are McLachlan’s “Building a Mystery,” one of her signature hits, from 1997, that inspired the documentary’s subtitle.

Born in a time when having even two women on a tour was considered untenable, and radio avoided playing women back to back, Lilith Fair’s legacy endures, as praised in the film by such next-generation fans as Olivia Rodrigo.

As Jewel, who played Lilith Fair in 1997, succinctly proclaims in the doc, “Women aren’t flukes.”

Count down The Biggest Hot 100 Hits by Acts Who Played Lilith Fair below, and listen along on Spotify.

The Biggest Hot 100 Hits by Acts Who Played Lilith Fair is based on actual performance on the weekly Billboard Hot 100 through the Sept. 27, 2025, chart. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. Due to changes in chart methodology over the years, eras are weighted to account for different chart turnover rates over various periods.



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