Cole: Lilith Fair was deemed passé. And in comes in the next: Backstreet Boys, ’NSync, Britney Spears, Christina Aguilera, and Jessica Simpson. It was very prefab, pop. I was releasing an album right around then, and I felt the backlash. I didn’t shave my armpits at the Grammys, and I got lambasted for that. It was so weird to me that that was such a big deal.

Molanphy: Sarah, Sheryl, Tracy Chapman, Jewel, Paula Cole, Fiona Apple were all pop acts, and that made the tour huge in ’97, ’98, and ’99. These women had done better than any women of their genre or ilk had ever done before. They all have gold or platinum albums. But they didn’t have 10-times-platinum albums. And by the time Lilith ends in 1999, Britney Spears and the Backstreet Boys are 10-times platinum, and the stakes have gotten so much higher. When the dust settled, and the last Lilith was over in ’99, they were women without a country. They didn’t have anywhere to go.

Schellenbach: Woodstock ’99 symbolized the end of female artists on the radio, ushering this new macho sound of Korn and Limp Bizkit. We rode to the top of this wave, and then it just crashed after Lilith. We had released an album, and just couldn’t find the support on radio because of Lilith backlash. It did have an effect on our trajectory. We broke up.

Sheffield: It was like, Wow. Where did all the girls go? You turn on rock radio, and there are no women at all. It wasn’t gradual. It was a very abrupt backlash between ’97 and ’99. All over the music industry.

McLachlan: I remember in 2000, the summer that Lilith didn’t tour, thinking, What happened? But you can only ride a huge wave for so long. Then it has to stop. And then something else comes along.

Eisenstein: 2001 or 2002, we were doing a WFNX-sponsored show in Boston. This was a time of Limp Bizkit. Backstage, the program director is talking to someone. Their conversation involved Lilith Fair. He goes, “Mark my words: That will never happen again.” He just thought that was like a fluke in history, that women would never have the popularity or power to put something like that together again.

Sheffield: Missy did her Ladies First Tour in 2004, with Alicia Keys and Beyoncé. It was Beyoncé’s first tour after Destiny’s Child. Missy said at the time, “I have been wanting to do something like this ever since I went out with Lilith Fair a few years ago.”

Warner: Sarah tried to do it again in 2010. I think it didn’t work because, partly, it was a couple years too early for this particular wave.

Diamond: Lilith in its last incarnation [in 2010] struggled. We struggled.

Fraser: No tours did well in 2010. It was a brutal year for Live Nation and the amphitheaters. Ticketing was an issue, and many people stayed away.

Powers: It was the timing, the economy, the state of touring—all of those things. Sarah was in her 40s when she revived it, so sort of the blowback women at midlife always get, like, How dare you think you can be the center of anything—you’re a woman past your prime. Perry Farrell is an interesting person to think about in relation to Sarah. Some people think he seems a little silly in his colorful world-beat shirts, but in all the versions of Lollapalooza, he never got that blowback.

“IT SEEMED LIKE IT HAD CONQUERED THE WORLD, AND THE WORLD WOULD NEVER GO BACK TO THE WAY IT WAS.”

Jaime Brooks: Lilith Fair itself was a great example of the inroads that women were making, in terms of maintaining control of their creative output. Then at the end of the ’90s, everything pop music goes into computers, and suddenly labels only trust producers and mixers. There’s less women in that field, and so suddenly everything goes right back in the hands of a bunch of antisocial men. And that’s a very dark, huge bummer.