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Lesbian Vagabonds: How Lilith Fair Shaped a Generation

Lesbian Vagabonds: How Lilith Fair Shaped a Generation

Colleen McGough was essentially a nomad. The ‘90s were a time of empty pockets and Top Ramen packets, staying in private housing and renting rooms overnight. She was a professional golfer in her 20s, for Christ’s sake; what did she care if she was always strapped for cash? 

During a tournament, her weeks were jam-packed, built entirely around golf. Monday, Tuesday, and Wednesday were for practice. Thursday, Friday, Saturday, and Sunday were for playing actual games, hoping to make the cut to continue in the tournament. Once she got paid, she was off, driving to the next event. Unlike the men, they had jack shit for money. 

Traveling all over the country, from event to event, Colleen formed tight-knit bonds with her fellow golfers. She and her friends, Stephanie Sparks and Leslie Henderson, or as she called them Sparky and Hollywood, lived as though they were carnies, upending their lives and moving nearly every week. New cities, new tournaments, new nightlife, same company.

In August of 1998, 24-year-old Colleen was in between tournaments on the Epson Tour, previously known as the Futures Tour, to qualify for the Ladies Professional Golf Association (LPGA) mini-tour. She planned to visit her best friend Julie in New York and then a girl she was seeing who lived in Massachusetts and attended Smith College. 

Saturday nights in New York City were expected to be nothing but a blur, and Colleen was known to get wild. She and Julie stayed out late, partying and drinking, until Colleen eventually retired to her great-aunt Ba’s house in New Jersey. She crashed on a makeshift bed on the living room floor. At 5:00 in the morning, the phone rang. 

Who would be calling at 5:00 in the morning? 

Ba wondered just that. She picked up the line, and there was a pause before she screamed into the living room, “Someone’s on the phone!” 

What the fuck? Colleen rolled over and got to her feet, hungover with a pounding headache. No consideration for her condition was taken into account when Sparky’s voice shot through the other line, “McGoo, wake the fuck up! We’re in Pittsburgh! We just got you a ticket to Lilith Fair! Hurry up and get down here — show starts at three! We’re gonna see Sarah!” 

What is happening? She was still half asleep, six hours away from her friends with no time to consider her options. Were there any? What would she have to consider? 

The festival was not short of critics, however, who called Lilith Fair “Lesbopalooza,” a jab at the queer artists, concertgoers, and booths set up for activist causes. Colleen, Sparky, and Hollywood were all gay, but according to Colleen, Lilith Fair was much less like the Dinah Shore than the public made it out to be. Though the media acted as though Sarah was finger-blasting everyone on stage, it was not so much an explicitly queer space as it was a space where people felt safe to be queer. In fact, Colleen was just beginning to come out at the time of the 1998 Lilith Fair she attended, and she found that the festival was comprised mainly of chicks and a lot of cute gay boys. 

Sparky, if anyone, would be into something like this. Tortured and dramatic, Sparky was both an artist and an athlete — a force to be reckoned with. When the three girls went out together, Sparky was always willing to grab the nearest acoustic guitar and rip out a Brandi Carlile. It was almost as if they were in a touring band themselves, the music of the time tying them together just as much as their careers. 

Colleen’s aunt Ba — and her aunt’s sister Helen — were wicked pissed about the last-minute schedule change, but she hit the road with barely a moment’s notice. This wasn’t an opportunity she was willing to pass up. Rushing out the door, still so painfully hungover, Colleen stopped at Dunkin’ for a coffee and a donut to keep her fueled for the drive, then smoked her way across the gorgeous state of Pennsylvania — Marlboro, Camel, or Parliament; it didn’t matter as long as they were light. 

Born on January 28, 1968, in Halifax, Nova Scotia, Sarah McLachlan grew up training in classical piano, guitar, and voice at the Maritime Conservatory of Music. It was a wonder she was discovered in such a town, so separate from the rest of Canada. However, Halifax is dynamic and full of life with seven universities and a world-renowned art school, the Nova Scotia College of Art and Design University (NSCAD), which Sarah attended for just one year prior to getting signed by Nettwerk. 

At age 17, she joined a band called October Game, but it was short-lived. During their first gig, Mark Jowett from Nettwerk approached her about working with his band, MOEV. Sarah’s mother essentially told her, “Like hell, you’re going off at 17 years old,” and encouraged Sarah to stay in Halifax and go to school while holding out for a better offer. Sure enough, Nettwerk came back two years later and offered her a five-record contract as a solo artist. 

Before she was the Grammy-award-winning singer-songwriter she came to be, Sarah was just another punk rock teenager with a skateboard. If she didn’t end up a singer, she would have been a jewelry or fashion designer, an artist of some kind. Creativity ran in her veins. Sarah’s friend, writer and director Buffy Childerhose, still has bracelets Sarah made for her when they were kids. They spent much of their time hanging out at a video arcade run by a local music promoter and smoking on the lawn in front of the library. It was where all the weirdos hung out. 

One night on the library’s lawn, Sarah pulled out her guitar and just started singing. Buffy didn’t know she sang or played, and she was dumbfounded by her voice. If she didn’t love her so much, she would have resented her for her talent.

Holy shit, she thought. This is not your average good singer. There’s something remarkable here. 

Over the years, Buffy and Sarah stayed in touch, doing so made convenient by their proximity to one another. Buffy, while living in Morin Heights, would go to the mountains when Sarah was recording just outside of Montreal, where she’d be able to watch her work. Though Sarah’s career was steadily advancing, she was becoming angered by the double standards woven into the music industry.

“We can’t play two women back to back,” programmers for radio stations would tell Sarah. 

When she wanted Paula Cole to open for her on tour, promoters told her, “You can’t put two women on the same bill — people won’t come!” 

Sarah decided she would take matters into her own hands if men would not listen to her. Her frustration manifested in the idea of a festival that only featured women. She began reaching out to musicians and singers from the folk, rock, pop, and country scenes, including Fiona Apple, The Cardigans, Sheryl Crow, the Indigo Girls, Emmylou Harris, Jewel, Joan Osborne, Dido, and Pat Benatar, among many others. So many performers agreed that she added a third stage, called the Village stage, where she could add 125 more acts.  

Sarah wanted to name the tour something along the lines of “The Girly Show,” but Madonna had already done her own “Girlie Show” tour in 1993 for her fifth studio album, “Erotica.” 

Maybe something like “Eve?”

“You don’t want to name something after Eve,” Buffy told her. “If you’re gonna go down that creation story, let’s take the proto-feminist.” 

Sarah had never heard of Lilith, but Buffy had read a lot about her — the figure from Jewish folklore who was said to have come from the same soil as Adam, celebrated for her struggle for independence when he tried to exert dominance over her. Chaotic, seductive, and empowering for women, she was also often thought of as wicked and demonic. Feminists celebrated her for being the first woman to challenge the oppressive systems under which she was born. 

Buffy thought it would be very telling to name the festival after a character who was like, “F all the way off. I am not going to be subservient to you. I’m not made from you. We’re made of the same stuff.”

From this conversation, Lilith Fair was officially born, and it was clear almost immediately that it was quite unlike any other festival at the time. Lollapalooza, for one, was a much more male-dominated environment featuring Devo, Beck, Porno for Pyros, The Prodigy, and many others in the year Lilith debuted. 

In the dead of summer, many women felt more comfortable wearing what they wanted at Lilith Fair — a safer, more welcoming environment. Buffy didn’t have to do calculus in her head, wondering if what she chose to wear would provoke some poor, poor man who couldn’t control himself. She could wear a bikini top and cut-off jeans if she wanted. 

Pittsburgh’s Star Lake Amphitheater was right on the river, and the weather was in the 90s the day Colleen went to Lilith with Sparky and Hollywood. In overalls and white boots, Colleen didn’t worry much about what she wore, but she was surprised she never felt as though she had to protect her girlfriends from guys circulating like great whites, back and forth, scoping out how drunk they could get their prey. She was actually able to enjoy the music above all else. 

She hadn’t been to many shows at that point in her life. As loud as Colleen was herself, she didn’t like loud music. She was never really “cool” — she was a golfer. Though with her lobes stretched, and her tongue pierced, she wasn’t lame either. Colleen fit right in at Lilith Fair.

The energy of concerts was often too stressful for her, the crowds suffocating and overwhelming. Lilith Fair was different; it wasn’t a sausage fest. You could really tear it up and let loose. 

Not only did women feel safer, but queer people also felt safe to be themselves. Colleen was vulnerable, still in the process of coming out, and she suffered from social anxiety. Even though the crowd was expansive, an undulating sea of skirts and flowy dresses, tank tops and sunglasses, the event felt much smaller than it really was. Cutting-edge lesbian artists like Luscious Jackson were inspirational to Colleen and many others who were not entirely accepting of their own sexualities along with the Indigo Girls, who Buffy thought of as the patron saints of queer folk music. 

A writer in her 20s at the time of Lilith Fair, Buffy didn’t want to buy the whole kumbaya-barefoot community of free-spirited women. What was so life-changing about it? She thought an event like Lilith Fair could easily promote “empty commercialism or naive sentimentalism.” 

However, it seemed the rumors were true. Buffy found herself taken by the energy of the restless crowd in just the first moments. Sweating under the summer sun, whispering and shouting the names of the artists they waited for, the audience rumbled in anticipation until Sarah walked out to welcome the audience to Lilith Fair. Audience members felt as though they were part of what was happening on stage, participating in the overall manufacturing of positive energy and community.  

Tour life is similar to summer camp in the sense that artists tend to get quite close over short periods of time due to their proximity. Though it is often assumed that gathering a bunch of women together in the same industry might spark competition, insecurity, and cattiness, the artists of Lilith Fair used the opportunity to collaborate and raise each other up. 

Community among the performers has been largely attributed to the Indigo Girls. They banged on dressing room and trailer doors — “Let’s go out, let’s go have a hootenanny!” — and suddenly, all of the musicians began hanging out and playing songs together, often trying to cram lyrics in before someone’s set so others could join them. 

With such emotional singers on stage, it was much more common for concertgoers to begin opening up about their own experiences and inner turmoil. It was much easier to have deep conversations with strangers without being drunk or high in a setting like Lilith Fair. The feeling of community was incredibly fluid, passing between performers, concertgoers, and vendors in the Village. Planned Parenthood had a booth, and a friend of Sarah and Buffy’s made jewelry that she sold at a booth in the Village, casting pharmaceuticals in sterling silver. As people stood around the booths buying jewelry, they began to talk to one another. Some wore the pieces as though they had talismanic value, like an evil eye, and others wore them as a way to dispel shame about using psychotropic medications. 

All Colleen can remember of the Village is merch, beer stands, and fair food. Sparky got stupid stoned and bought an order of french fries while Colleen ordered beer for herself. The two of them found a spot to settle down on the grass with Hollywood. 

When a woman with silvery-blonde hair walked out with an acoustic guitar, Colleen couldn’t help but wonder, Who’s this old fucking geezer getting on stage? Emmylou Harris shut her down immediately — and blew her doors off. That was her dad’s chick. She never expected her to be cool

On the second stage, performer Heather Nova found that both onstage and behind the scenes, audience members and artists alike exchanged generous and free-flowing energy. She finally felt like she was being heard and celebrated in a big way, honored Sarah invited her to participate in something so revolutionary. After singing a rendition of Bruce Springsteen’s “I’m on Fire” with her cellist, Sarah asked her if she could accompany her on the song for the rest of the tour. Each night, the festival ended with Sarah coming onstage to invite the performers from the day to sing Marvin Gaye’s “What’s Going On?” They’d each take a line and sing choruses together.

At the end of the night, happy-go-lucky from the day and on their way back from Bridgetown, Colleen, Sparky, and Hollywood hit up some fast food restaurant Sparky grew up eating at. As soon as they got back to Sparky’s house, the three of them fell asleep, exhausted and renewed all at once. 

Today, at age 50, Colleen McGough’s life is much different. She lives in Bend, Oregon with her girlfriend, and it is the longest she’s ever stayed in one place — three years. Colleen wears thick, black glasses that take up most of her face, and she remains unafraid to tell it like it is, her voice raspy from smoking cigarettes in her youth. She stopped playing golf in 1999, but she went back to get her class A teaching credential for the LPGA, and she retains professional status to this day. 

At 56 and 55, Sarah McLachlan and Buffy Childerhose have been friends since they were little punk rock teenagers. Sarah’s daughters now wear Thrasher sweatshirts, and Buffy jokingly refers to them as posers — “Your mom can skate, you cannot. Get that off.” Sarah regards Lilith Fair as “one of the most meaningful and joyous events” in her life, something that “needed to be done.” 

From the suffragettes in the 1840s and ‘50s fighting for the right to vote, to their mothers in the 60s and 70s fighting for the right to abortion, Buffy and Colleen recognize that Lilith Fair didn’t happen in a vacuum. The festival was born from a need for change and representation in the music industry. Since its three-year run from 1997 to 1999, there has yet to be another festival quite like Lilith Fair. From the folksy singer-songwriters of the 90s emerged the hypersexualized popstar archetype of the 2000s, where women in music morphed into an item to be bought, rather than admired for their art and their writing. 

Though the music industry remains dominated by men, womenand queer people continue to fight for their voices to be heard. Lesbian singer-songwriter Chappell Roan has repeatedly shattered the glass ceiling this year alone, drawing in the largest crowd Lollapalooza has seen in its history, so large they had to move her from the second stage to the main stage to accommodate the swarm of fans. However, this level of success is far less common for women even today.

Melody Caudill, lead singer and frontwoman of Career Woman, takes part in a very do-it-yourself pocket of the music scene. Raised on many women artists like Erykah Badu and Jill Scott, Melody recognizes how the angry, punk attitude in today’s music has been passed down from the ‘90s women like Liz Phair and Alanis Morissette. She admires the badass big-name bitches in pop, like Sabrina Carpenter and Charli XCX, and Melody finds herself also appreciating the talents of newer lyricists like Clairo, Mannequin Pussy, and Samia. Though women are visible in the music scene now more than ever before, Melody also recognizes that there are still so many roadblocks for women behind the scenes. 

Off of Fairfax and Melrose in early July of 2023, Melody set up for a show in the back of Ghengis Cohen, a Chinese restaurant known for hosting small bands. A crowd gathered around the stage as she sang, backed by drummer Allen Moreno, bassist Joey “Reto” Chavez, and guitarist Jackson Felton. Audience members swayed with the lyrics to her song “Unfun.” 

“I feel so unfun / I won’t even smoke a blunt,” she sang, and Joey mimed smoking a joint while audience members laughed good-naturedly. “The last time I went to a party / I sat in the kitchen and rearranged the pantry.” 

Though she loves her fellow bandmates to death, Melody feels as though gigs can sometimes be hostile and unwelcoming. She finds she is often apprehensive to insert herself in conversations she rightfully belongs in. Older men approach her bandmates first in professional settings, even though she’s the one in charge. Setting up her gear on stage is a nightmare because if she has a question or needs help, she’s afraid she’ll come off as unprofessional or under-qualified. When men talk to her as if she doesn’t know what she’s doing, Melody is reminded of these gendered power dynamics.

Photo by Tristan Padron

She attributes this phenomenon to there simply being more eyes on you when you’re a woman. Women in the spotlight are criticized more heavily and scrutinized more closely than their male counterparts. Chappell Roan has faced backlash for speaking up about harassment she’s been receiving from fans since her rise to fame, and Sarah McLachlan received critiques on the lack of diversity in her festival lineups for Lilith Fair. 

Melody’s outlook on fostering a welcoming energy at her shows stems from the belief that kindness comes first. Attitude and energy are incredibly important when putting on a show. Even if she’s trying to put away her shit, and everyone is in her face all at once, Melody stops. She is nice. Music is too important of a space to be the one to ruin someone else’s experience.

The days of Lilith Fair have passed, and should there be another festival like it, Melody ventures such an event would have to be much more diverse, including more groups of people and identities. The “spirit of female artistry” and the “articulation of the female experience” continue to evolve in the face of patriarchy, and Melody pushes onward, alongside many other queer and woman artists, toward a safer and more inclusive music industry.

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