Sarah McLachlan performs at the 2010 Lilith Fair at Capital Federal Park at Sandstone on July 15, 2010 in Bonner Springs, Kan.

Sarah McLachlan performs at the 2010 Lilith Fair at Capital Federal Park at Sandstone on July 15, 2010 in Bonner Springs, Kan.

Jason Squires/WireImage

The men had a nice long run of it. But in 1997, it was ladies first, last and in-between on stages across North America during the inaugural voyage of Lilith Fair, an all-female touring festival named for the ancient figure from Jewish folklore purported to be Adam's first, wanton wife.

Conceived by gauzy Canadian alt-pop singer Sarah McLachlan as well as her management and agent, the antidote to the testosterone-fueled antics of tours such as Lollapalooza and Ozzfest was a kinder, gentler day at the amphitheater. But it was also a loud, proud message about female solidarity and the box office power of women in the face of what was initially a hard-sell to some promoters, who had trouble at first wrapping their heads (and wallets) around it.

Outside of the underground Michigan Womyn's Festival -- a more radical gathering of feminists and folks singers which ran from 1976-2015 -- the concept of putting more than one woman on a mainstream tour was, believe it or not, considered a radical notion at the time. "That whole idea lit a fire under our butts," McLachlan says about the two-women-too-many murmurings from some industry veterans. "That stupid attitude became a kind of banner that we waved!"

So, McLachlan, her Nettwerk Records label bosses/manager Terry McBride and Dan Fraser, and New York talent agent Marty Diamond made it happen with a 35-city tour featuring more than 60 artists that ended up grossing $16 million to take the festival touring crown in its first year. The mind-blowing lineup that first year that included McLachlan, Suzanne Vega, Sheryl Crow, Tracy Chapman, Jewel, Paula Cole, Mary Chapin Carpenter, Fiona Apple, Joan Osborne, The Cardigans, Emmylou Harris, Lisa Loeb, Indigo Girls, Shawn Colvin and India.Arie, as well as such second stage acts as Cassandra Wilson, Dido, Victoria Williams, Beth Orton, Patty Griffin and Juliana Hatfield.

The idea was hatched the year before, when McBride was looking for a way to coax McLachlan back on the road after an extended hiatus that followed her three-year tour in support of nearly triple-platinum breakthrough 1993 album Fumbling Towards Ecstasy. "She came home pretty burnt out and went into hibernation for nine months and didn't want to do anything musical," McBride tells Billboard. "So Dan and I said, 'You have to get back into it -- maybe do some summer shows?'"

McLachlan agreed, but insisted that any dates include another female headliner -- her singer-songwriter pal Cole, about to become a household name thanks to her top 10 pop hit "Where Have All the Cowboys Gone?" the following year  -- and on Sept. 14, 1996, the beta test for what quickly morphed into Lilith Fair took place in Vancouver. That trial run wouldpave the way for an eventual three-year run that would not only prove that women were a powerful box office draw, but also raise more than $10 million for charity and provide a stage for some budding stars of tomorrow.

After some initial gripes about a lack of diversity, future line-ups mixed and matched artists as far ranging as Raitt, Des'ree, Erykah Badu, Garrison Starr, a then-unknown Idina Menzel, Neko Case, Sinéad O'Connor, Sheryl Crow, Queen Latifah, Tegan and Sara, Susan Tedeschi, Nelly Furtado, Liz Phair, Mya, Luscious Jackson and Monica.

The gang tried to get the band back together in 2010 for a Lilith reboot, which McLachlan dubbed "a disaster," due to thin attendance and the defection of some headliners (Carly Simon, Kelly Clarkson, Queen Latifah, The Go-Go's and some others), which led to nearly one-third of 36 planned dates getting canceled. "It didn't have the same feeling and it wasn't being done for the same pure reasons," McLachlan says.

But in honor of the 20th anniversary of the original run's July 5, 1997, launch at The Gorge amphitheaters in George, Washington -- which drew more than 27,000 attendees -- Billboard spoke to McLachlan, McBride, Fraser, Diamond and first-year tour mate singer Tracy Bonham about the origins, impact and legacy of the Lilith Fair.

The Idea

Terry McBride (CEO/Co-Founder Nettwerk Music Group, McLachlan manager 1988-2011): She didn't really want to headline, so we had to get other people. She put in for other talent and said, "They all have to be female." That was another challenge. So with Marty booking the talent, we put a show together and she had the time of her life playing with Paula, Lisa Loeb and Suzanne Vega [during 1996 test shows in Burbank and Berkeley and a gig in Vancouver that was officialy called "Lilith" and drew more than 10,000]. We we put that first show up, and it did so well, we put a smaller version on in Los Angeles and San Francisco. So then we got the branding and trademark going and officially launched it in 1997. 

Sarah McLachlan: I was having writer's block and I was home. When I stay home too long, I get restless. I liked the idea of a few shows, but I didn't want to do a whole tour. Terry was like, "Why don't you do a few shows with artists you've played with before, like Paula Cole, and ask a few other women [as well]?" That sounded like fun and really natural because I didn't want to have a whole show on my shoulders. And the artists we asked said yes, and the promoters we worked with said it sounded fun. 

I had played theaters, and all of a sudden I was in front of 16,000 people and I thought, "This is kind of amazing. I could maybe do more of these." At the end of the four shows we said, "Let's do this next summer."

Marty Diamond (McLachlan's former agent at Little Big Man): Those test shows proved it would work, but there were a lot of naysayers. "No one will spend money to see a bunch of women play," is what we would hear. There certainly had been smaller events that existed that were women-centric, but this was a different idea.

McBride: It came off so authentically, we thought, "We have to do this next summer." It wasn't a reaction to anything else. A lot of promoters really didn't like the idea of two female artists playing together, and I'd tell Sarah that, and she'd say, "Why?" And all we could say is, "We don't know. We don't get it personally, we think it's a great bill." But in the business then, it was 90 percent run on the live side by men, and radio was 90 percent run by men. From that point of view, Lilith was counterintuitive.

Diamond: There was definitely a gap in the landscape. At the time the charts weren't heavy with Beyoncé, Rihanna, Taylor Swift and Katy Perry. Women didn't dominate the charts and radio the way they do now.

McBride: After the first show in Detroit [on June 14, 1996] there was less opposition. We really had to really prove it and we did -- which made the second year so much fun, because we weren't trying to persuade people to get involved. Nettwerk created a rainy-day fund in case it didn't do well to help get it off the ground... a couple hundred thousand dollars, which in those days was a s--tload of money for us. We didn't lack in belief, but we also didn't want to go down the drain.

McLachlan: It was a natural progression, and when we went out the next year, the promoters that didn't know what we'd done said that [you can't put two women on a bill]. But that stupid attitude became our banner! That was a time of Soundgarden and Pearl Jam dominating the radio waves and festivals, and you wouldn't think twice about hearing two of those bands in a row. But if they added Tori Amos that week, they'd say, "We can't add you too, but you're in the running." That seemed like such a ridiculous attitude.

So, because women were being clumped together like that we created a festival with all women clumped together. It was a grand f--k you!

The First Year

Dan Fraser (Nettwerk Managment President, co-founder Nettwerk Music Group): From the promoter side, there were tours like Lollapalooza and H.O.R.D.E., and in 1996 there was also Ozzfest. We would come in and follow Ozzfest around in 1997, and they'd rip up the lawn and it would be a mud pit, and people were like, "Thank God you came along!" It was very different then. There was a lot of angst in festivals back then.

Diamond: I wasn't really surprised by the reaction and success, because I was confident we'd put together a good lineup. And there were certainly challenges... anything that becomes successful people look for chinks in the armor. There's the ongoing agenda item dealing with matters of cultural and racial differences. There was commentary about the festival being too white. It certainly started that way, and our intention wasn't to be that way. We approached several other artists that passed, or it didn't work out at that time. But there was more hip-hop, R&B and international stuff as we went on, and it was part of an ongoing dialogue.

McLachlan: My first reaction was I wanted to do this because it was so much fun! It was, "How exciting. Let's do this for a summer." Then someone said we couldn't do it, it won't succeed, so we were determined to prove them wrong and we did. Because it was created out of a true intention, a good intention. It was not premeditated, there was no grand scheme behind it other than it was a lot of fun and we get to do this every day. I love playing live and touring and sharing the stage... I got to sing with so many heroes. To share the stage with those women was powerful stuff. 

Tracy Bonham (played 1997/1998 Lilith Fair): My first album [The Burdens of Being Upright] came out in 1996, and I was touring around as a rock act trying to distance myself from the singer/songwriter thin. Because in the 1990s, that was not cool. I was out on the road and my manager said, "I guess Sarah McLachlan is putting together this thing with all girls," and I remember going, "OH NO! I'm not doing that!" I was already fielding so many questions from the press about "What does it feel like to be a woman in rock?"

But the cool part was Sarah personally called me, and that was kind of great. At first I wondered how my music fit in, but what Sarah taught me is it didn't matter -- we were joining forces, and it was cool that we all had completely different backgrounds and sounds. I was on the same bill as Missy Elliott, Bonnie Raitt and The Cardigans. What I learned from her is, "Let's celebrate everyone."

McLachlan: I'd been an opening act before and not treated well, so I made sure backstage we were all treated the same -- the crew, the bands -- I wanted a great experience for everyone. I was very involved with picking the artists, and putting a wish list together. I worked on relationships I already had and crossed fingers and hoped others would buy in.

I also got some flak because it was deemed by some as a "white chicks festival" that first year, which was eye-opening for me because I'd always lived my career quietly until that point, and been blessed to be a media darling. I defended it in the sense that we asked a lot of artists based on who I am, and what they assumed it would be. But based on the success [of the first year], they looked at it and said, "This might be interesting for my artist." I knew after the first couple shows that it was going to work. The second year, it was much easier to get artists from different genres, because that first summer was such an eye-opening experience.

Making a Difference

McBride: The thing that was very different about Lilith was it went with the local community. It was not a traveling show to get as much money as we could. There was a component where a local artist opened up Lilith Fair, and that same artist was on stage at the end of the show. And everyone came to the press conference before that day's show, because we got to hand a local charity a check that came from a dollar per ticket. For many, that was $15,000-$20,000, which was the difference between staying open or not. The impact on those artists was incredible... they realized they had made a significant difference in the community they played to.

McLachlan: The only reason I could stomach the press conferences was that we would could give sometimes a $33,000 check in Minneapolis to a women's shelter, and to know we're not only putting on a show, but also leaving behind a bit of a legacy. This good energy was being carried forward. For me that was a big part of it, like being an ambassador for kindness. It solidified how good it feels to live your purpose, to know you're doing something meaningful and leaving a lasting mark. 

Fraser: A lot of those organizations were women's shelters that couldn't advertise who they were, because they lived in the shadows in their city and it was hard to fundraise, they had to be so anonymous. And these women hiding their lives to recover from what was going on, they would come up and tell us, "You can't know how much this means to us." When they saw the size of the check -- sometimes hundreds of thousands of dollars -- they would break down. We did 100 shows; with all the sponsor dollars we raised more than $10 million.

McLachlan: For me, the [festival's] legacy is [how] all the money I made from Lilith i put into my foundation, where we have afterschool programs for at-risk populations in Vancouver, Surrey and Edmonton, through the Sarah McLachlan School of Music.

Bonham: I'd never played a festival like that before. It was mostly male-dominated ones. In Europe it was different, but in the U.S. it was starting to get really macho, and this was a nice alternative. I was worried about being pigeonholed... but it's hard to say no to a really good thing. The positives were so positive, there was so much love in the air. Especially considering what came after, with things like Woodstock '99. 

Fraser: We were the first ones to put a stage in the middle of the lawn with artists playing the village stage in the middle of 12,000 people on grass. They might go from playing to 75 people in a club the night before to 12,000. Now tours put a B stage in the middle of the lawn all the time.  We also had the village component with a traveling group of vendors, Planned Parenthood booths and big corporations... all realizing that gals are the household CEOs and they will spend money.

McBride: I had never heard of a burqa, and 20 years ago we had a lady who came on our whole tour with a mannequin dressed in a burqa, educating people about how women were treated in different parts of the world. There were so many eye-opening moments like that. It was a great place to have a respectful conversation about life and issues, without all the anger. 

Fraser: I was really lucky I got to see all of them. But whether we had 45,000 at a race course in Minneapolis or 20,000 at am amphitheater, people would pick up after themselves. The lawn would look pristine. There was a sense of community and no division between race or sexes or genres, no divisions. That's why everyone gets into the music business.

Backstage Memories

McLachlan: As an artist you're often isolated in this bubble alone on the road. So it was great to create that energy where it was a very respectful, safe environment backstage. From the first day, I wanted everyone to know that this was going to be fun, everyone will be treated well, nobody is an a--hole. I created an environment where everyone can just relax, which took a while, because I'm a bit shy. But I would knock on doors and say, "Hey, if you need a backup singer, I'm here." I played with Bonnie [Raitt], with so many of them, and it was exactly what we all hoped for -- just a great hang where we all wanted to play together and have a great hang. 

I remember having a great conversation with [the Pretenders'] Chrissie Hynde when she first came on board -- Sheryl [Crow] was there -- and [Hynde] said, "You know, I don't know about this thing." I think I laughed at her and said, "F--k you, I'm glad you're here." And she was like, "Okay, that's how it's going to be?" She might have called us "precious bitches" and I said, "You're going to have fun, sweetheart."

One night she was playing "Middle of the Road," and I decided to come out and do this ridiculous dance. It was her last nigh,t so I wore this ridiculous pink tube top and I flashed her, and realized I'd flashed the whole band. She laughed so hard she fell down on stage in front of 16,000 people. 

Fraser: One of my favorite moments was a show when it was pouring rain, like a monsoon, and Sheryl Crow came out with a snorkel, mask and fins and thanked the crowd for sticking in there.

Diamond: Almost every night there was the group encore, which was usually Sarah or the Indigo Girls poking the stick to get it going. It was always a big deal, and a lot of discussion about what song it would be and who would kick it off. But it always felt like a discussion. Everyone felt like a peer, whether they were on the third stage or main stage. 

Bonham: People hung out backstage, and it was cool. I was sitting next to Suzanne Vega at catering and Bonnie Raitt sits down, and the three of us had been produced by Mitchell Froom -- and she was like, "Hey, it's Mitch's Bitches!" Then, later on when I was in my dressing room, Bonnie walked in again and she sits on the couch and says, "Do you want to come out and play 'Angel From Montgomery' with me?" So I start practicing my violin licks in E Flat, hopefully not too fast, and when we played together it was the most beautiful thing I'd ever heard. 

McLachlan: They [Indigo Girls] probably suggested it because they had been doing folk festivals for years, and they knew the game better. But I knew we had to do something, and I wanted everyone to come and have a free-for-all. It was really fun, and one of these magic moments where sometimes it was great, and sometimes we fell on our asses. My favorite ones were were every artist was on stage and everyone wanted to participate. It was great to see people stick around all day to the end to be part of it, because sometimes you just want to play your 45 minutes and disappear.

The Legacy

McBride: We had so much to prove to the overall business that first year. You have to remember, back then there wasn't a radio format when we started that supported female music. By the second year there were 30-40 hot AC stations across most major cities playing predominantly female artists. That was a huge deal, and the lasting legacy is that the hot AC format was created because of Lilith.

Bonham: It was really radical. It celebrated female artists in a very male-dominated business and it became very successful despite of it. 

Diamond: I think it changed the paradigm and the way radio looked at things in terms of female artists at the time. It certainly changed the concert business in terms of women coming out to see women. I think it broke down barriers of a collective of women being able to sell tickets, whether it was Sarah, or Sheryl Crow or Natalie Merchant, many, if not most still have strong music careers and are still active touring artists and creative people.

There was a degree of mentorship that went on there. VH1 did a Behind the Music [episode about Lilith], and they're always looking for controversy. But there wasn't a lot of controversy. These were people who willingly and openly wanted to play with one another. 

McLachlan: The vibe on stage translated. Everyone understood what it was and they felt like they were part of something special. We were the highest-grossing tour of that summer, but I was the loudest proponent of putting the brakes on [after the 1999 edition]. Everyone else would have loved a fourth or fifth summer, but I saw the fatigue on all of us. It was time to quit on top.

I don't know why nobody has tried it again. Music shifted then [in 1999] when we finished, and boy bands were becoming huge as the pendulum swung back toward male artists. People keep saying, "You need to bring it back!" and we tried in 2010. But it was a colossal failure, because the intentions were not as pure.

I am not who I was back then. If it were to succeed today it would have to be someone new to carry the torch, a new artist... and it doesn't have to be called Lilith. It can be someone else. With the women's march and Trump in power everyone is banging on my door, "We need to bring this back!" No, we don't. But someone of this moment should create something different because this time is very different.