Glamorous Trash: A Celebrity Memoir Podcast

Episode: Documentary Book Club – Lilith Fair: Building a Mystery
Host: Chelsea Devontes
Guest: Jana Schmieding
Date: November 21, 2025

Episode Overview

This episode of Glamorous Trash delivers a lively, thoughtful book club-style deep dive into the Hulu documentary "Lilith Fair: Building a Mystery." Host Chelsea Devontes and returning guest Jana Schmieding – a self-described "Lilith Fair girly," writer, comedian, and podcaster – dissect the history, legacy, and cultural impact of the iconic all-women 1990s music festival founded by Sarah McLachlan.

The discussion traverses the festival’s radical vision, the gender politics of the music industry, issues around representation and diversity, and the resonance of Lilith Fair’s ethos today. Laced with nostalgia, humor, frankness, and pop culture insight, this conversation both celebrates Lilith Fair’s achievements and critically examines its place in feminist and music history.

Key Discussion Points and Insights

1. Personal Connections and Lilith Fair Nostalgia

• Jana attended Lilith Fair three years running as a high schooler in Portland, OR.
  • She shares: "I went to all three when they came to Portland... I put weed on a bagel because I didn't know how else to sneak in weed to the concert... and did not get high." (05:48)
  • The festival was pivotal: a space for "choir nerds" and "folk woman vibes" outside the male-dominated music spaces (like Warped Tour).
• Chelsea admits she entirely missed the Lilith Fair moment.
  • "I thought it was a singular fair... like Woodstock. In fact, it was the largest traveling tour of all time..." (07:28)

2. Radical Vision and Logistics of Lilith Fair

• The industry said you couldn’t put two women on the same bill; Lilith Fair proved them wrong.

  • "[Promoters] said you can't put two women on the same bill... People won't come." (03:38)
  • "Of course women had to do 10 times the work of a normal festival and fucking put it on semi trucks to get the acclaim that say, a Woodstock has." – Chelsea (07:07)

• Women ran the festival at every level:

  • Female crews got jobs traditionally reserved for men (like moving equipment, running sound).
    • "It was a top to bottom kind of redoing the industry..." (08:49)

3. Sarah McLachlan’s Influence & Personality

• McLachlan emerges as a composed, visionary leader.
  • Chelsea: "On personality alone, the way she handles herself and put it together... She changed the entire music industry." (10:03, 13:28)
  • Jana: "She's not a messy... she's sort of like Canadian ren fair." (13:49)
• Documentary surprise: Many signature TV and movie anthems of the era were Lilith Fair artists.
  • Jana: "All of their songs were the TV themes and movie themes in a way that I don't feel like people credit a Natalie Merchant enough. Or Suzanne Vega or Meredith Brooks." (15:19)

4. Culture Wars, Gender Politics, and Softness as Rebellion

• Contrast to Woodstock 1999 / Male-Centric Festivals:
  • "Lilith Fair was happening at the exact same time, making so much money, so successful, and being this very soft space where that shit [violence, misogyny] didn't happen—and how it was made fun of and lambasted and a punchline in culture..." – Chelsea (17:09)
• Internalized Patriarchy:
  • Jana notes much scorn for Lilith Fair came from women too: "I've talked to so many women my age... they're like, 'oh god.' I think it's internalized patriarchy." (18:17)
  • The music was dismissed as “lame” or “for lesbians,” which points to broader cultural discomfort with women-centered spaces.
• The power of women writing and performing their own stories.
  • Chelsea: “People go nuts for it now, as we see with Taylor Swift, Olivia Rodrigo, Lily Allen’s latest album…” (19:56)

5. Representation and Racial Diversity Critiques

• The hosts praise diversity efforts, especially as the festival evolved:
  • Jana: "I saw Maya at the Lilith Fair and... she was not only an amazing performer, but also was a tap dancer..." (26:20)
• But note the challenge of representation:
  • Chelsea: "Bringing women together in one concert tour becomes political… the tour had to speak for all women... It's so tough how Lilith Fair had to speak for every single woman alive..." (23:34)
  • Yet, Sarah and the organizers were open to critique and course-corrected to include artists like Missy Elliott, Erykah Badu, and Tracy Chapman.
    • Jana admires: "[Sarah] said, 'That's fair. Let's adjust our tour.' ...I wish that's how everyone responded to this." (26:44)

6. Feminism, Money, and the Burden of ‘Goodness’

• Concert proceeds went to charity:
  • Chelsea ponders if the expectation for women to donate/“be good” is both self-imposed and societal:
    • "I think we are expected to be caregivers, to be selfless..." (31:08)
  • Jana adds, "I don't know if capital is our whole thing... The spirit of this tour is sort of like, we just want to make music and we want people to listen to our music and let us on stage." (28:20)

7. Lilith Fair’s Ending, “Peplum Years,” & Attempted Revival

• Lilith Fair ran for only three years; revival in 2010s flopped.
  • "She says, I have to learn that you can't be everything to everyone. And that's painful to learn." (36:16)
  • Chelsea: “The actual, like, come and spend your money on women’s art, didn’t work [in 2012].”
  • Jana: "But it is gonna be a struggle... Like, in my own life, I went and I struggled through the same shit... That, I think, is the legacy of Lilith Fair..." (37:12)

8. Final Reflections: Lilith Fair’s Legacy & What We Need Now

• The festival’s spirit lives on in new iterations of female-centered art, but current industry economics (Ticketmaster, streaming) make collective tours hard.
• Chelsea’s rallying cry for a new era:
  • “If there was some sort of Lilith Fair in any space, comedy, authors, whatever... like, I'm going to the all-female shit. Or... anti-patriarchal space, whatever gender it is, I think we need it really badly right now in all areas of life.” (40:21)
• Jana points to Brandi Carlile as a modern torchbearer: "Brandi Carlile, I call on you to find 10 indie female artists and go on a tour with seats." (41:49)

Notable Quotes & Moments

• “I will even watch the bad [music documentaries] and have a good time. Oh, me too. This is a good one.” – Chelsea (05:33)
• “It was so cool to see this moment where 15 women were playing guitar at you the way men always have.” – Chelsea (21:55)
• “Some of the biggest haters of Lilith Fair are women... It’s internalized patriarchy.” – Jana (18:17)
• “You can't be everything to everyone. And that's painful to learn.” – Sarah McLachlan, quoted by Chelsea (36:16)
• “The legacy of Lilith Fair is that we saw it was possible and we just have to replicate it in our own lives.” – Jana (38:08)
• “If there’s an artist that is doing it, it is Brandi Carlile.” – Jana (41:58)

Timestamps of Key Segments

• 01:16 – Episode theme and format introduction
• 03:38 – Industry doubters and the festival’s radical premise
• 05:48 – Jana’s first-hand Lilith Fair nostalgia (weed on a bagel anecdote)
• 09:59 – Fashion eras as markers (e.g., “Empire waist” dresses of '90s, “peplum years” of 2010s)
• 13:28 – Sarah McLachlan’s impact and transformation of industry practices
• 17:09 – Lilith vs. Woodstock 1999: contrasting festival cultures
• 18:17 – Dismissive attitudes and internalized patriarchy
• 23:34 – Representation, box-checking, and challenges of inclusion
• 28:20 – Feminism, money, and expectations for goodness
• 36:16 – Lilith Fair’s finale and lessons learned: you can’t be everything for everyone
• 40:21 – Calls for new feminist spaces, the struggle against hyper-capitalist music industry
• 41:49 – The next Lilith Fair: who will build it?

Memorable/Must-Listen Moments

• Jana’s high school festival stories and “weed bagel” caper (05:48)
• Chelsea’s realization about what she missed and fashion as cultural signifier (09:59)
• Honest discussion of the burden placed on “women’s events” to represent all women (23:34)
• Deep candor about early 2000s “false feminism” and the lessons of Lilith’s failed comeback (36:16–38:58)
• The thriving spark of women collaborating, learning from the Indigo Girls, and dropping solo competition (33:28)
• The finale: a vision of what a new Lilith Fair could look like (40:21–41:58)

Closing Notes and Recommendations

• Check out Jana’s podcast “Sage Based Wisdom.”
• Lilith Fair: Building a Mystery is streaming on Hulu.
• Playlist: Jana promises to share her Lilith Fair–inspired iTunes playlist with listeners.
• Big picture takeaway: Lilith Fair was both a product of and an answer to its time—an enduring model of women’s artistic community and activism, still needed in new forms today.