Brandi Carlile watched Lilith Fair at 15 and knew, 'I want to do that.'
1. True Crime Obsessed recaps the 1997 documentary `Lilith Fair: Building a Mystery`, centered on Sarah McLachlan's all-women festival.
2. Hosts Jillian Benzavalli and Patrick Hines treat the film as personal history, and Hines says Paula Cole may be "the greatest singer of our time."
3. The episode's core question is why a lineup of Sarah McLachlan, Paula Cole, Sheryl Crow, Tracy Chapman, Suzanne Vega, and the Indigo Girls felt radical in the 1990s.
4. McLachlan opens the documentary by explaining Lilith as Adam's first wife, who leaves Eden rather than surrender equal treatment.
5. The hosts say 1990s radio programmers would not play two women back-to-back, and McLachlan remembers being lumped with Tracy Chapman and Jewel.
6. They use clips of Bill Maher, David Letterman, and Howard Stern to show how public conversation around Monica Lewinsky, Jennifer Aniston, and Suzanne Vega was openly sexist.
7. McLachlan describes a Los Angeles record-label meeting where she was told to lose five pounds and fix her hair.
8. She responds by building Lilith Fair with low guarantees and a simple idea: put women on the same bill and prove the promoters wrong.
9. Sarah McLachlan invites Paula Cole first, and the early two-woman tour sells strongly enough to grow into a larger festival.
10. Lisa Loeb says the concept felt risky at first because she did not want to be boxed into 'the girl with the glasses,' but the lineup changed her mind.
11. The first Lilith Fair roster includes Sarah McLachlan, Paula Cole, Tracy Chapman, Suzanne Vega, Cassandra Wilson, Fiona Apple, Joan Osborne, and the Cardigans.
12. The documentary shows backstage footage of Sarah McLachlan and Sheryl Crow rehearsing, which the hosts treat as proof that the festival was built around collaboration.
13. Brandi Carlile appears in home video at the first Gorge show as a 15-year-old fan, and she says the experience made her want to do the same thing.
14. Paula Cole performs 'I Don't Want to Wait' at the piano, and the hosts connect that song to her later 1990s visibility on `Dawson's Creek`.
15. The crew discussion is unusually concrete: forty festival shows, women roadies, sound engineers, and extended health care.
16. One crew story has grown men crying because the festival's insurance let their children finally see a dentist.
17. Suzanne Vega says the backstage mood was stiff until the Indigo Girls arrived and broke through the distance by singing with everyone.
18. Brandi Carlile says watching the Indigo Girls and other women perform without apology showed her that she did not have to worry about seeming 'too gay' or 'too feminist'.
19. The episode notes that Lilith Fair generated about $60 million over three years, while Sarah McLachlan donated $1 from each ticket to local charity.
20. The segment ends on the Grammy aftermath, where Paula Cole won Best New Artist, Sean Colvin won Record and Song of the Year, and the three women were given a medley instead of separate performances.
