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Lilith Fair Headliners Who Never Stopped Rocking

There was a time before dubstep. A time before Coachella and Bonnaroo. An age when you'd actually turn on the car radio, and when you did, more often than not what you'd get was some kick-ass, classic girl-and-guitar music. The 90s was a heyday of lady-singers, and with the raging resurgence of the decade's fashion trends, we're hoping those ladies come back too. Even if they don't, we always have the shower. From Lisa Loeb's sweet ballads, to Melissa Etheridge's torch songs, to Ani DiFranco's acoustic calls to revolution — these were the voices that shaped our younger days. We've rounded up our fifteen favorites (it was a very angsty week here at R29) and shared some classic videos. Best of all, when you're done, we've crafted a Spotify playlist of the all-time greatest lady-singer hits of the 90s. Break out your Docs and that acoustic guitar in the back of your closet. It's going to be a good weekend.
The Lovers
Sarah McLachlan
Currently rocking the charts with unwatchable ASPCA ads, Sarah McLachlan was the earth mother of the Lilith Fair set. Songs like "Ice Cream" and "Adia" virtually defined this period of lady-music, and no one ever topped her vocal flip skills. Regardless of how you feel about her now, pop on Surfacing and you’re going to want to put on some overalls and drink coffee out of an oversized mug.
Mock all you want, there was a time when every girl had a Jewel song in her back pocket. Certain writers of this article may or may not still know the chords to "You Were Meant For Me" and will gladly whip out a rendition should you give her a cocktail. Or even if you don’t. Do you want to hear it right now?
Jann Arden
On the mushier side of things, there was Jann Arden, singing earnest poppy torch songs about lost love. Forever associated with a certain kind of soundtrack (she’s featured in Dawson’s Creek, My Best Friend’s Wedding, and unstoppably gushy Bed of Roses), Arden’s achy-breaky love songs are best sung at full volume, driving down the highway with the windows down, until you’re crying.
Lisa Loeb
Oh, sweet Lisa. Was there anything better than those two weeks you listened to nothing but "Stay", driving your parents up the wall and developing a desperate case of glasses-envy? No. Lisa embraced the girly side, but that in no way diminished her power as a musician. She let us be angry and angsty, and still love kitty cats.
Indigo Girls
If you never spent an afternoon trying to perfect an acoustic rendition of "Galileo" with your best friend…well, sorry, you didn’t have an adolescence. Like Melissa Etheridge, their vocal style was of the loud-and-raspy type, but the Indigo Girls could sing about the fun and breezy times with as much gravity as the heartache. We never felt more flannel-y as when these ladies were rocking our Sony Discman.
Image: via The Lilith Fair
The Ragers
Alanis Morissette
Alanis!! Thank goodness Jagged Little Pill came along or we never would have realized just how angry we were in seventh grade. The floorboards of our childhood bedrooms will never be the same for all the angry stomping they suffered upon the release of "You Oughta Know". She’s still out there touring all the time, but we’re the ones in the crowd screaming for an acoustic encore of "Mary Jane".
Melissa Etheridge
When it comes to post-break-up obsession, no one did it better than Melissa Etheridge. Her lyrics were stripped of all hesitation and her brash, raspy voice gave everything she sang a heavy dose of sincerity and depth. Drop everything and listen to "Come To My Window" right now, then come back and read the rest of this when you stop crying. The woman could add gravitas to a Burger King commercial. She’s just that good. (PS: Do not miss Gwyneth Paltrow, plus five inches of eyeliner starring in this video! )
Leah Andreone
When we were really looking for a whine, a pout, or a full-blown middle-of-the-day cry, Leah Andreone brought the A-game. There was no middle ground — this girl was just upset (at her mother, at her dad, at her exes, at her pants) and she wasn’t afraid to share. Though she only had one radio hit with "It’s Alright It’s Okay", we like to think it brought a little necessary angst to mainstream.
Juliana Hatfield
If you ever stood up at a coffee house open-mic night, odds are good that you sang a Juliana Hatfield song (it was "My Sister", wasn’t it?). Then she had a My So-Called Life cameo and suddenly there was a line of a hundred Doc-Martened chicks behind you, all waiting to make the crowd weep with their renditions of "Make It Home". Don’t worry, we know you were there first.
Meredith Brooks
Sure, she was a one-hit wonder — but it was quite a hit. Meredith Brooks took all those things the other lady-singers were implying through metaphor and imagery, and just straight-up said it. "Bitch" got stale after eons of Top 40 replays, but whenever it pops up on a Sandra Bullock-vehicle soundtrack, we still secretly sing along quietly (or really, really loudly, if no one’s home).
The Revolutionaries
Ani DiFranco
Ani was the kick-ass soundtrack to our fifteen-year-old rage and vague attempts at feminist activism. We didn’t have the words to describe that particular anger that comes from when you just got dumped, you hate the president, a creep just hit on you, and also you’re about to get your period — but she did. Thank God.
Tracy Chapman
It almost hurts to relegate the legendary Chapman to one decade, but you can’t deny that her melodies lit up the 90s like no one else. This was the music both you and your mom liked, for once. Though her first album was released in 1988, featuring such classics as "Fast Car" and "Talkin’ Bout a Revolution", it became the soundtrack to long evening drives for years to come.
Paula Cole
Okay okay, try to forget about Dawson’s Creek for five minutes (we know, but try). There’s a lot more to Paula Cole than a truncated version of one radio hit. "This Fire" was a strange, dreamy mix of piano and guitar-heavy ballads (remember "Where Have All The Cowboys Gone?"). And more than anyone, Paula represented the Lilith Fair aesthetic, with her long-dress, sh*t-kickers, unshaven armpits, and cool-girl attitude.
Joan Osborne
Who could forget when Joan Osborne broke onto the scene and everyone freaked out over such controversial lyrics as “If God had a name, what would it be and would you call it to his face.” In retrospect, it all seems ridiculously tame, but we still kind of love that a pop song (and a catchy one, at that) had people utterly up in arms. Years later it became the theme song to a TV show, but Joan spent the 90s being threatened with excommunication — a rock ‘n roll right of passage.
Dar Williams
In terms of next wave folk, you won’t find better than Dar Williams. Her range went from heart-wrenching melancholy to bright, cheery tunes that felt like children’s music for adults. Her bouncy "As Cool As I Am" had us doing those particular dancing-around-in-your-undies moves that only certain songs invoke. Her haunting ballad "February" made us sit in the car in the driveway until the song was finished. "I Won’t Be Your Yoko Ono" gave us a great line to deliver to confused boyfriends.
Had enough? Of course not. Enjoy this 90s lady-singer playlist, featuring all these rocking females, and many more.

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