The Bridge: Lilith’s Winding Road

Summary

Hit Parade: The Bridge – “Lilith’s Winding Road”
Slate Podcasts | Hosted by Chris Molanphy | July 17, 2020

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Episode Overview

This episode of Hit Parade’s bonus series “The Bridge” explores the history, impact, and cultural legacy of Lilith Fair, the all-woman touring music festival that surged in popularity in the late 1990s. Host Chris Molanphy is joined by acclaimed music critic Jessica Hopper, whose oral history of Lilith Fair for Vanity Fair inspired the discussion. The episode delves into why Lilith Fair became a landmark, how its organizers curated its distinctive lineup, and what made it such a transformative experience for artists and audiences—especially women—in a male-dominated industry.

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Key Discussion Points and Insights

The Genesis and Vision of Lilith Fair

• Curatorial Strategy:
  Jessica Hopper compares Sarah McLachlan and the Fest’s organizers to baseball’s "moneyball" approach. Rather than banking on a single superstar, they compiled a diverse slate of artists with overlapping—but distinct—fan bases, ensuring every city’s lineup appealed to a wide audience.

  • “They kind of moneyballed it... they got together and did actually quite a bit of research about, you know, who in this…what artist in this city, this market could draw, you know, 7,000 people, who could do 20,000, who could do five.” – Jessica Hopper (04:00)

• Breaking Industry Barriers:
  Many women artists, despite successful records and loyal followings, hit a "venue ceiling" and struggled to access the large stages their popularity warranted. Lilith Fair allowed them to break through those barriers collectively.

  • “There was definitely a ceiling around what sort of a venue a larger women artist could get into.” – Jessica Hopper (05:30)

Why Lilith Fair Worked—and What Made It Special

• Community and Safety:
  Hopper emphasizes that Lilith Fair delivered a unique sense of community and safety otherwise lacking at mainstream festivals. For many women, this was their first music event where they felt comfortable and welcome.

  • “People wanted to go to a festival…those spaces fundamentally didn’t feel very safe to them. And they thought they would be safe at Lilith, and they were.” – Jessica Hopper (06:05)

• Setting Up Future Success:
  The positive experience of safety and belonging fostered audience loyalty and helped drive the festival’s success into its second and third years.

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Notable Quotes & Memorable Moments

• Jessica Hopper (04:00): “They kind of moneyballed it… they did actually quite a bit of research about who in this city, this market could draw… if they could get all these different artists that had fan bases that maybe overlapped but weren’t exactly the same and they made the bill really strong, they could get folks, and they did.”

• Jessica Hopper (05:30): “There was definitely a ceiling around what sort of a venue a larger women artist could get into, you know, namely Sheryl Crow, who was one of the headliners.”

• Jessica Hopper (06:05): “People wanted to go to a festival…those spaces fundamentally didn’t feel very safe to them. And they thought they would be safe at Lilith, and they were. And so because of that, the feeling of Lilith… it did feel like a safe space. It really, really made them want to go back and I think that really set up years two and three.”

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Important Segment Timestamps

• 01:06 – Chris Molanphy introduces Paula Cole’s “Me” and connects it to Lilith Fair.
• 02:17 – Introduction of guest Jessica Hopper, her background, and her Vanity Fair oral history, “Building a Mystery.”
• 03:54 – Hopper explains Lilith Fair's "moneyball" approach to building a bill.
• 05:30 – Discussion of the barriers women musicians faced in the touring industry.
• 06:05 – Conversation about festivals as safe spaces and Lilith Fair’s unique community appeal.

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Tone and Style

The conversation is both nostalgic and analytical, mixing chart trivia and industry insight with a deep appreciation for the revolutionary nature of Lilith Fair. Molanphy’s tone is inviting and inquisitive, while Hopper provides both expert critique and personal reflection, making the episode accessible for seasoned fans and newcomers alike.

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Summary Takeaway:
“Lilith’s Winding Road” illuminates how Lilith Fair was more than a concert—it was a pioneering event that redefined the live music experience for women. Through deep research and personal stories, the hosts show how its cultural impact still resonates, driven not just by talent and timing but by an inclusive vision and an audience hungry for community.

Transcript

[A]

You're listening ad free on Amazon Music.

[B]

Hey there Hit Parade listeners. What you're about to hear is a preview of our latest episode of the Bridge. As we announced recently, Slate is getting hit pretty hard by what's going on with the economy in the wake of the COVID 19 pandemic. We need your help to continue producing this show and all the other work we do at Slate. So we're asking you to sign up for Slate plus our membership program. It's just $35 for the first year and it helps support us at this crucial moment. Sign [e-mail] hitparadeplus and you'll get to hear this and every episode of Hit Parade in full. That's slate.com hitparadeplus thanks. And now your episode preview.

[A]

And it's me who's too and it's me who's too shy to ask for the thing I love.

[B]

Hey everybody, this is Chris Melanie, host of Hit Parade, Slate's podcast of pop chart history. Welcome to the Bridge. That's Me, a song by Paula Cole from her 1996 album this Fire. In the lyrics, Cole sings about crossing a bridge into self acceptance and self love. Cole performed Me as a mainstage act at Lilith Fair in 1997 and 98. The All Woman touring festival helped raise her profile as a hitmaker. Issued as the third radio single from Cole's album, Me reached the top 40 on Billboard's Radio Songs chart in the spring of 1998. And these mini episodes, Bridge are full length monthly episodes give us a chance to catch up with listeners and enjoy some Hit Parade trivia. This month I am delighted to have two very special guests, an esteemed writer and an old friend of the show. Let's talk to our writer Guest first. Jessica Hopper is an acclaimed critic whose work has spanned more than two decades and a range of publications including Rolling Stone, the New York Times Magazine, gq, the Guardian, Elle, and Bookforum. She was a longtime contributor to the Chicago Reader and a columnist for the Village Voice, Chicago Tribune, and Punk Planet, as well as the music consultant for this American Life for eight years. Her books include the Girl's Guide to Rocking, the first collection of criticism by a living female rock critic, and Night Moves, her deeply researched September 2019 piece for Vanity Fair, Building a Mystery, An Oral History Lilith Faire informed and helped inspire my latest episode of Hit Parade. Jessica Hopper, welcome to the Bridge.

[A]

Thank you for having me, Chris. I'm happy to be with you.

[B]

And thank you again for having me participate in your Very comprehensive Vanity Fair piece on this subject last fall. I think we talked last summer at this time, and it was. It was a lot of fun reminiscing about Lilith Faire. And the crux of your piece was that Lilith was a big deal in its day. It was the top grossing touring festival in its first year. You even called it visionary. So what do you think made Lilith exceptional and what made it work for its time?

[A]

I think there were a few things that really contributed to its success. You know, first and foremost, they really put together a bill that, you know, they kind of moneyballed it, you know, if people are familiar with that, where, you know, they got together and did actually quite a bit of research about, you know, who in this. What artist in this city, this market could draw, you know, 7,000 people who could do 20,000 people who could do five. And when you look at these bills, they're really quite stacked. It wasn't that these artists were going to be drawing, you know, that Amy man and Sean Colvin and Lisa Loeb and Sarah were all going to be drawing, you know, the exact same audience, that there really was this idea that if they could get all these different artists that had fan bases that maybe overlapped but weren't exactly the same and they made the bill really strong that they could get folks, and they did. You know, I think another reason that it was successful was that these audiences were really, in some ways fairly desperate to connect with a community around. Around these artists. And some of these artists had only been able to kind of tour and play venues up to a certain point. But even though they were, you know, their sales and their audience would have justified bigger venues because they got to a certain point and they really faced. There was definitely a ceiling around what sort of a venue a larger women artists could get into, you know, namely Sheryl Crowe, who was one of the headliners. It's called Every Day is a Winding Road. And then I think. I think there was kind of maybe under this. That they only really discovered once Lilith came to be a great success. And I know this from interviewing quite a few people who were. Were audience members as part of the oral history and research for it was that people wanted to go to a festival. And when I say people, I mean primarily women and young women. They wanted to go to a festival, they wanted to go to a concert. And those spaces fundamentally didn't feel very safe to them. And they thought they would be safe at Lilith, and they were. And so because of that, the feeling of Lilith, I think that for some people who went, it did feel like a safe space. It really, really made them want to go back and I think that really set up years two and three.

[B]

Thanks for listening to this episode. Preview to listen to the Full Hit Parade episode, please go to slate.com hitparadeplus.