1. Sarah McLachlan: “Building a Mystery”
Though music of Lilith Fair has an unfair reputation for being soft and maudlin, this hit from Sarah McLachlan’s 1997 album “Surfacing” — released the same month that Lilith Fair began — is a razor-sharp portrait of a man who wears his eccentricities on his sleeve. “You wear sandals in the snow and a smile that won’t wash away,” she sings in that chiming tone. “Can you look out the window without your shadow getting in the way?”
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2. Fiona Apple: “Sleep to Dream”
Percussion rumbles like trembling earth at the beginning of this opening track from Fiona Apple’s 1996 debut album “Tidal,” setting the stage for the introduction of a major talent. “This mind, this body and this voice cannot be stifled by your deviant ways,” she proclaims, her words unfurling in a jazzy cadence. “So don’t forget what I told you, don’t come around, I’ve got my own hell to raise.” Did she ever.
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3. Tracy Bonham: “Mother Mother”
Tracy Bonham phones home and tells her mother a cathartically screamed lie — “Everything’s fine!” — on this alt-rock gem that effectively captures the anxieties of early adulthood. Its success is also a stark reminder of how few female voices broke through in the years after Lilith Fair: When it hit No. 1 on Billboard’s Modern Rock Tracks chart (later renamed Alternative Songs), it would be the last song by a female solo artist to top that chart for 17 years, until Lorde’s “Royals” did in 2013.
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4. The Cardigans: “Lovefool”
This bubbly 1996 hit by the Cardigans was unavoidable, and impossible to get out of your head, in the late ’90s. Though the frontwoman Nina Persson was the group’s sole female member, the Swedish pop-rock band was among the headliners of the first Lilith Fair.
▶ Listen on Spotify, Apple Music or YouTube
5. Tracy Chapman: “Give Me One Reason”
Tracy Chapman — who made a memorable appearance at this year’s Grammys — was another of the first year’s headliners. Luke Combs’s recent cover brought a new generation of fans to Chapman’s 1988 hit “Fast Car”; now who’s going to tackle this bluesy rocker from her 1995 album “New Beginning”?
▶ Listen on Spotify, Apple Music or YouTube
6. Emmylou Harris: “Wrecking Ball”
Lilith Fair wasn’t all ’90s superstars. It was an intergenerational space where younger performers could meet and share the stage with elder stateswomen like the great Emmylou Harris, who had recently released her pivotal 1995 album “Wrecking Ball.”