I went to Lilith Fair in its inaugural year (1997) for one reason and one reason only: Sarah McLachlan. It might be hard to believe now, but before her breakout album “Surfacing” dropped the same year that Lilith Fair began, McLachlan was seen as a unique alternative artist. Before making us all feel guilty that we weren’t saving enough dogs (can anyone hear “Angel” without thinking of that poor, limping pooch in the ASPCA commercial?), McLachlan was on the edge of the mainstream, but not truly in it.
I saw her live for the first time in 1994 at the Vic Theatre in Chicago, where she put on an astounding two-hour singing exhibition. At the time, she was touring in support of her third album, “Fumbling Towards Ecstasy.” My favorite track on that record is a song called “Fear,” a daringly arranged song that stretches McLachlan’s mezzo-soprano to the edge of its range. I might have bought my ticket just to hear her sing that one song. Once I heard the first notes of “Fear,” I felt some trepidation. Would she be able to do it live? Sure, every song she performed before coming to “Fear” that night was exceedingly well sung, but there are levels to the singing game, and that song is on the top shelf.
As the first notes left her lips, I sat in my chair astounded. She didn’t cheat on the record. She didn’t have to. She had that much voice. I’ll never forget it.
McLachlan’s blockbuster “Surfacing” came four full years after “Fumbling Towards Ecstasy,” and free of the ASPCA stigma, it can be enjoyed as an excellent album in its own right. In support of her best-selling recording, McLachlan created Lilith Fair, a movable feast of a festival that featured only female artists.
The ‘90s were the era of the touring music festival. Peter Gabriel had WOMAD, punk had the Warped tour, the metalheads had Ozzfest, and freaks like me had Lollapalooza. WOMAD aside, what all these festivals had in common was a dearth of female performers. Pre-2000, it was highly unusual for two female acts to tour together. Hell, it was rare for two female artists to be heard back-to-back on the radio. The business was run predominantly by old men who didn’t believe that an all-female bill could sell tickets. McLachlan set out to change that with Lilith Fair.
The lineup of the show I attended in Tinley Park, Illinois, included Lisa Loeb, Jewel, Tracy Chapman, Sheryl Crow, Emmylou Harris, McLachlan, and closing out the evening, The Indigo Girls. In truth, the only artists taking the main stage that I had any interest in were Chapman and McLachlan. After McLachlan completed her set, I was actually ready to go, but one much wiser person than I in our group (a woman, of course, who now works for the ASPCA – some shit, you cannot make up) insisted on staying to see the Indigo Girls close the show.
On that evening, I learned a new appreciation for two particular artists on the bill: Emmylou Harris, who has become a longtime favorite, and the Indigo Girls, who, with just two voices and two acoustic guitars, turned that outdoor arena into a 45-minute sing-along. I looked around me and saw all these mostly young women (and some men), raising their voices in concert with the Indigo Girls (Amy Ray and Emily Saliers). As the other performers took to the stage and joined the duo, it became clear that the woman who told me “no” was right, not just for herself, but also for me.
Lilith Fair was like no other concert I’ve ever been to. On the amusing side, the wait to use the men’s bathroom was so short that I at first thought I was going through the wrong door. The women’s bathroom was another story. That line to the loo had multiple bends in it. In fact, the line was so long that some of the ladies dumped decorum to the side and just used the boys’ room. At the time, I thought it was merely funny that the men’s room had turned co-ed. But now, all these years later, I’ve come to realize something else: those women felt safe.
The world is not set up to provide girls and women with security. But on that night twenty-eight years ago, in a place just outside of Chicago, men weren’t just the deep minority; the men that were there were less likely to be handsy, or far worse. Looking back on it now, I feel some silly sense of pride that I was among the number of the happy few, non-threatening fellas who came into a microcosm of a world that wasn’t created for us, but made us welcome, even if I was the dumb ass who wanted to skip town early.
Sarah McLachlan did that. At the time, she wasn’t even thirty, and she was more than a little afraid. But in this very defined space on this very unique tour, she showed just how well women could run a logistical beast of a roving event with kindness, decency, empathy, and most notably, success.
In the year 2025, I feel so very far removed from my festival concert days. The exposure to different sounds, cultures, and perspectives opened my mind and the minds of others. Now, it is as if minds are closed before the opportunity for exposure even presents itself. “Pre-closed,” you might say.
Lilith Fair: Building a Mystery serves as far more than a time capsule or a piece of nostalgia. It presents McLachlan and her tour mates operating in a different way and on a different frequency. A frequency I deeply hope we can find again.
Lilith Fair: Building a Mystery is available to stream now on Hulu & Disney






