True Crime Obsessed – Episode 477: “Lilith Fair: Building a Mystery”

Release Date: December 18, 2025
Hosts: Patrick Hines & Jillian Bezavali

Episode Overview

This bonus episode sees the hilarious and heartfelt team of Patrick and Jillian diving into the documentary “Lilith Fair: Building a Mystery – The Untold Story.” The episode isn’t their traditional true crime fare but a lively look at the iconic 90s women’s music festival, Lilith Fair. Patrick, a self-proclaimed Lilith Fair superfan, is especially moved, while Jillian offers the viewpoint of a less-immersed music lover. Together, they break down not just the history of the festival, but its cultural impact, the challenges the women faced, the festival’s legacy, and what made Lilith Fair so special — all with their trademark humor and sharp commentary.

Tone: Enthusiastic, nostalgic, irreverent, sometimes emotional, always feminist.

Key Discussion Points & Insights

The Weight of Lilith Fair’s Legacy

• Lilith Fair’s inception: Sparked by Sarah McLachlan’s refusal to accept music industry sexism, where “two women on the same bill” was considered a commercial risk ([04:12–04:23]).
• Patrick’s nostalgia: Lilith Fair represented a transformative time for Patrick – his college years and the last era he “really cared about music” ([02:32–03:14]).
• Multi-genre female headliners: Noted for bringing together icons like Paula Cole, Sheryl Crow, Indigo Girls, Tracy Chapman, and more ([04:12], [20:28]).
• A symbol of feminist progress: The hosts stress Lilith Fair’s importance in both feminist history and music history ([03:40–04:00]).

Industry Sexism & “The Real Crime”

• Radio programming rules: The hosts discuss the misogynistic “rule” of not playing two women back-to-back on the radio ([06:24–07:04]).
  • Jillian: “Radio program directors didn’t want to play, like, too many women... It was a rule. It was like an actual rule.” ([06:24])
• Pressures on female artists: Tales of record executives asking Sarah McLachlan to lose weight and “fix her hair” – an industry focused on looks over talent ([15:14–15:31]).

The “Lilith” Myth & Name

• Reclaiming Lilith: Sarah McLachlan took inspiration from the mythological Lilith, the first woman to refuse to submit. The hosts revel in the symbolism ([07:18–07:41], [21:11]).
• Jillian on the rebranding: “She demon slut baby stealers sound fucking awesome.” ([21:11])

The 90s: Toxic Press & Double Standards

• Sexualization and assault: Jillian and Patrick critique notorious 90s TV moments where male hosts harassed female artists ([10:30–11:32]).
  • Jillian: “The way Howard Stern is trying to force himself onto Suzanne Vega on camera is so fucking disgusting.” ([11:32])
• Multiple perspectives: Acknowledgement that not every female artist agreed with Lilith Fair’s ideology — some opted out, and the festival’s ethos wasn’t monolithic ([12:18–12:32], [44:19–45:02]).

Founding Female Friendships and Collaboration

• Sarah & Paula Cole’s duo tour: The initial tour broke industry rules and demonstrated fan demand for women supporting women ([18:09–19:11]).
• Community over competition: The Indigo Girls acted as the festival’s “welcome wagon,” fostering backstage collaboration and emotional connection, making it “camp” ([31:38–33:11]).
  • Documentary Interviewee: “They were somehow part of the glue that held all that emotionally together for those women.” ([34:09])

The First Festival and Behind-the-Scenes Stories

• The inaugural lineup: A who’s who of 90s talent, spearheaded by McLachlan, Crow, and Chapman ([24:25]).
• Brandi Carlile’s origin moment: As a 15-year-old attendee, Lilith Fair guided her towards a music career ([25:46–27:06], [67:33–68:22]).
• Paula Cole and “I Don’t Wanna Wait”: Before Dawson’s Creek made it famous ([30:08]).

Diversity & Growing Pains

• Year Two Criticisms: The festival drew criticism for being “Lily White Fair” — lacking diversity ([43:47–44:19]).
  • Event Organizer/Staff: “We need to really do outreach… live in the solution, not the problem.” ([43:47])
• Expanded lineup: Year two brought Erykah Badu, Missy Elliott, Queen Latifah, India.Arie, Desiree, aiming for greater inclusivity ([46:27]).
  • Patrick on Missy Elliott: “She was on this broke down bus that broke down on the side of the highway… She gets there, puts on her inflatable suit and it happened.” ([47:09–47:47])

Activism, Motherhood & Safe Spaces

• Charity at the core: Lilith Fair donated $1 of every ticket to local charities ([36:07]).
• Pro-choice advocacy: Planned Parenthood was a festival partner — leading to protests, bomb threats, and Texas venues attempting to exclude them ([57:06–58:56]).
  • Joan Osborne: “I have a long history working with Planned Parenthood and being a volunteer for them, so it just incensed me.” ([58:41])
• Backstage as safe haven: Babies everywhere, artists pregnant or breastfeeding, and an environment uniquely supportive for mothers in music ([55:17]).

The Press, Awards & the Grammy Medley Controversy

• Women grouped together: The Grammy's decision to lump nominees together for a “Lilith Fair medley” rather than individual performances annoyed the artists ([40:39–41:09]).
• Paula Cole’s armpit moment: Her unshaven armpits made headlines, overshadowing her historic wins ([41:20], [42:02–42:51]).
• Jillian: “That’s all anybody talked about because it gave the idiots everything they wanted… But first of all, that sounds like a blast.” ([41:44])

When Lilith Fair Collided with 90s Bro Culture

• Woodstock ’99: A pointed contrast to Lilith Fair – rampant violence and misogyny versus “peace, love, and getting along” ([61:19–62:19]).
  • Sheryl Crow (quoting herself): “The day I got back, I ran into Sarah’s arms and sobbed into the bosom of the founder of Lilith.” ([63:55])

The End of an Era & Its Enduring Impact

• The final show: Rain-soaked and emotional in Edmonton, Alberta, with Sarah McLachlan sending fans off with gratitude and pride ([65:08–66:13]).
• Why it couldn’t last: The 2010 revival flopped; cultural shifts made the original formula less resonant ([66:56]).
• Modern resonances: Today’s women in music — from Taylor Swift’s “Eras Tour” to Olivia Rodrigo and Brandi Carlile — owe part of their path to Lilith’s legacy ([67:15–69:14]).

Notable Quotes & Memorable Moments

• Patrick (on Lilith Fair’s significance):
  “This just hit me at exactly the right time. These were my college years. I was – this was the last time that I really, really cared about music.” ([02:32])
• Jillian (on industry sexism):
  “Radio program directors didn’t want to play, like, too many women on the radio stations... It was a rule.” ([06:24])
• Sarah McLachlan (documentary):
  “Lilith was Adam’s first wife before Eve. 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...” ([07:18])
• Event Organizer/Staff:
  “We had a bomb threat. People want to blow us up…” ([04:47])
• Brandi Carlile:
  “...The Indigo Girls, they were somehow part of the glue that held all that emotionally together… seeing those women on stage unconcerned with whether it made them look gay or overtly feminist or angsty or angry or any of the things that Indigo Girls are getting thrown at them.” ([34:09])
• Paula Cole (on the Grammy medley controversy):
  “So in my stupid fucking unmusical medley, I happened to raise my hand and… I didn’t shave my armpits.” ([41:20])
• On challenges and evolution:
  “As many accolades as we were getting, we were getting slammed every once in a while being called Lily White Fair — that there wasn’t enough diversity in year one.” ([43:47])
• Patrick (closing):
  “Sarah McLachlan creating Lilith Farrer inspired hundreds of thousands of people. But one of them was Brandi Carlile, who was like, ‘I want to do that.’ And then she went and did it...” ([68:22])
• Erykah Badu (documentary):
  “It was just a village of very intelligent, very powerful, very creative, very mission-oriented, very strong women who are staying together, putting a period at the end of a sentence.” ([69:18])

Timestamps of Important Segments

• 01:41 - Lilith Fair documentary recap kicks off
• 04:12 - Early lineup and industry doubts
• 06:24–07:04 - Radio’s “one woman at a time” rule
• 13:10–15:31 - Sarah McLachlan’s struggle with industry beauty standards
• 18:09–19:11 - Sarah & Paula Cole’s initial duo tour
• 24:25–25:01 - Sheryl Crow and Tracy Chapman join
• 25:46–27:06 - Brandi Carlile’s formative Lilith experience
• 30:08 - Paula Cole’s “I Don’t Wanna Wait” pre-Dawson’s Creek
• 31:38–33:11 - The Indigo Girls and festival camaraderie
• 40:39–41:14 - Grammy awards and the infamous medley
• 41:20–42:51 - Paula Cole’s armpit controversy
• 43:47–44:19 - Addressing diversity criticism
• 46:27–47:47 - Missy Elliott’s festival debut
• 55:17 - Backstage motherhood and safe spaces
• 57:06–58:56 - Planned Parenthood’s involvement & protests
• 61:19–62:19 - Lilith Fair vs. Woodstock ’99
• 65:08–66:13 - The final Lilith Fair
• 67:33–68:22 - Brandi Carlile brings it full circle
• 69:18 - Erykah Badu on the village of strong women

Themes & Takeaways

• Lilith Fair was a radical act: Bringing women together wasn’t just about music; it challenged deeply held industry and cultural norms.
• Music as empowerment: The festival created safe space for both artists and fans — especially young women and queer people — to see themselves on stage.
• Constant pushback: Despite commercial and critical success, the festival still struggled with misogynistic backlash, internal criticism, and cultural ignorance.
• Legacy: Even though Lilith Fair couldn’t last forever, its impact is still felt, having inspired a generation of artists, activists, and fans.

For Further Listening

• Patrick’s must-hear: Paula Cole’s “This Fire” album
• Jillian’s must-hear: Fiona Apple’s “Tidal” and discography

Final Reflections

Patrick and Jillian end with gratitude for being able to relive and analyze such a pivotal movement in music and feminist history, reminding listeners to check out music from all the artists discussed, embrace the spirit of Lilith Fair, and to keep pushing for spaces that lift everyone up.

End of episode summary