I Covered the Lilith Fair as a College Journalist — and Now the Documentary is Making Me Miss 1998

For those of us who are old enough to remember the late 1990s, the Lilith Fair: Building a Mystery documentary is a nostalgic ode to a bygone era that celebrated women in rock music — and empowered a generation of feminists.

But for young college journalists like me who covered Sarah McLachlan’s festival in the summer of 1998, the Hulu documentary is especially bittersweet.

It’s not just that I miss the 1990s and the women who inspired me to pick up a guitar — like Liz Phair, a 1998 Lilith artist, as well as Courtney Love and PJ Harvey. I also miss living in a time when I didn’t worry about my freedom, body autonomy, or body hair. I could enjoy live music without feeling compelled to whip out a cell phone to capture it. I miss being a student reporter at The Diamondback at University of Maryland, excited to enter the profession of journalism upon graduating in 1999.  

Watching the documentary (directed by Ally Pankiw) brought me back to so many of my favorite 1998 moments — Missy Elliott wearing an inflated black vinyl getup and performing “The Rain (Supa Dupa Fly),” McLachlan belting out “Building a Mystery,” and Phair, armed with her trusty guitar, launching into “Polyester Bride.”

I still recall how ecstatic I was to score pair of complimentary press tickets to one of the two Merriweather Post Pavilion Lilith Fair dates (July 18, 1998) and attending the pre-show press conference under a big outdoor tent. I specifically remember McLachlan telling us what she’d apparently been telling journalists all summer: “It’s just like summer camp.” 

The documentary does an excellent job of balancing such “behind the scenes” footage in the press tent and backstage with scenes from grassy amphitheaters across the country, where concert goers experienced the Lilith Fair firsthand. What’s especially sweet is the documentary’s footage of impromptu backstage jams between McLachlan and other main-stage artists, including Sheryl Crow, Paula Cole, and The Indigo Girls.

These scenes, interspersed with one-on-one interviews with Lilith Fair big-stage acts Jewel, Crow, Cole, Erykah Badu, Suzanne Vega, and others, truly showcases what the festival felt and looked like: We see the sold-out, mostly female crowds enjoying the sun and music, cheering as their guitar-wielding and microphone-clutching lady heroes perform their biggest hits. We see the merch booths, the sponsor tents, the big and small stages — everything that made the festival utopic.

Interviews with 22-year-old Gen Z pop superstar Olivia Rodrigo and millennial folk-rock sensation Brandi Carlile, 44, offer a unique perspective of how Lilith’s folklore inspired the next generation of artists who might have performed in the Fair had they only been born sooner.

“I was in disbelief that I’d never heard of it before,” Rodrigo says in the documentary’s trailer, echoing the sentiments of many of her Gen Z peers on TikTok, who now speak wistfully of the event in the way Gen X’ers still speak about the 1969 Woodstock Music Festival.

As actor Dan Levy, who produced the documentary, noted, Lilith Fair was the place where queer kids like him — he was 14 when attended the Fair — felt love and acceptance they didn’t feel in other spaces.

Of course, it wasn’t all bliss and rainbows back then, and documentary doesn’t shy away from less-utopic topics, including the difficult conversations about diversity (and the dominance of white female folk artists), and pushback from religious groups and figures like Jerry Falwell (who criticized naming the festival after a she-devil in Christian mythology).

Lilith persevered in spite of these and other challenges, and most would now say the Fair was ahead of its time in diversifying its line-up, donating proceeds of ticket sales to women’s causes, and offering a cultural counterpoint to what musician Jewel recalled as the dominant culture of “shock jocks” and toxic masculinity.

She’s absolutely right about that: Festivals like The Warped Tour, which ran every summer from 1995 until 2019, featured a teeny tiny percentage of female-led acts (which necessitated Shiragirl’s 2004 Warped Tour uprising). The heavily male-act-dominated, Woodstock 1999 concert — which Lilith Fair artist Crow played — is more frequently remembered as a human rights disaster than a sweet resurgence of the original 1969 gathering. 

But what made the documentary difficult to watch was the same thing that made it incredible. Watching the film, I was reminded that, 27 years after attending the Lilith Fair, I’m still starving for the collective musical sisterhood I witnessed then. I’m not sure I’ll ever experience anything like Lilith again. While bands like No Doubt still headline festivals like Coachella, female-fronted bands barely account for more than 30% of most festival lineups.

“The music festival lineup is nowhere near equal,” Melinda Colaizzi, founder of Women Who Rock, told me in a 2024 interview.

The desire to rekindle Lilith or recreate something like it may be growing again. It’s no coincidence that Indigo Girls’ campfire favorite, “Closer to Fine”” has experienced an epic resurgence long after the Barbie came out in 2023. This song, a Lilith Fair favorite, is now the quintessential anthem for the kind of sisterhood many of us took for granted in the late 1990s, when we thought that we were on the verge of full-blown gender equity.

Perhaps foolishly, I’m still hopeful. As I watched McLachlan perform her new single “Better Broken” on Jimmy Kimmel Live! last week, I recalled sitting barefoot in the grass at Merriweather Post Pavillion on the evening of July 18, 1998, with my best friend Bethany, watching Natalie Merchant belt out “Carnival.” Seeing McLachlan, now a mom, perform on Jimmy Kimmel (after initially not performing, in protest of his show’s hiatus) reminded me how important it is for women to amplify our voices. I hope younger artists, especially female singer-songwriters born after 1999, do not take their opportunities, for granted. It’s high time for the next radical idea (that would make McLachlan proud) to materialize.