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10 massive hits that defined the late-'90s Lilith Fair era

Jess Huddleston

21 years ago, Sarah McLachlan assembled the first all-female line-up of artists who would hit the road as part of her traveling music festival, Lilith Fair. A response to underrepresentation and misogyny in the music industry, McLachlan’s rotating sisterhood — which included some of the biggest pop, rock, R&B and rap acts of the '90s — would go on to be one of the most talked-about, highest-grossing music festivals from 1997 to 1999.

The chart-topping roster of Lilith Fair talent varied from city-to-city, year-to-year, but one thing was constant — iconic female artists were united on stage in solidarity, all while churning out some of the most memorable songs of the decade.

Here are 10 hits from the Lilith Fair era that will bring you back to an incredible time in music.

'Building A Mystery,' Sarah McLachlan

On founding the all-female touring festival, McLachlan told Rolling Stone, “It was like, ‘Well, if you’re not gonna have any female artists on your tours, we’re just gonna do it ourselves.’” As the biggest hit off her multi-platinum 1997 album Surfacing, the opening chords of “Building A Mystery” ignited deafening roars from the crowd when McLachlan closed out each night of the Lilith Fair tours.

'Doo Wop (That Thing),' Lauryn Hill

The Miseducation of Lauryn Hill is one of the defining albums of both hip-hop and the late-’90s, putting the ex-Fugees member and triple threat on the global map. “Doo Wop (That Thing)” is unsurprisingly the most history-making single of the Lilith Fair years, being the tenth song in the Billboard Hot 100 chart history to debut at number one, and the first debut single to do so. Joining select tour stops of the 1998 Lilith Fair festival, Hill was just a budding solo artist at the time, but this legendary banger undoubtedly got concert-goers out of their singer-songwriter trances, and onto their feet.

'Where Have All The Cowboys Gone?,' Paula Cole

One of the first to join McLachlan’s Lilith Fair lineup, late-’90s sensation Cole is best remembered for this sexy lead single as well as (the Dawson’s Creek theme song) “I Don’t Want to Wait,” both off her 1997 album, This Fire. The song went on to be nominated for three Grammys, including best new artist, which Cole won.

'Kiss Me,' Sixpence None The Richer

While the entirety of the pop-rock band’s 1997 self-titled album was excellent, it was this Grammy-nominated single that would go on to become one of the most unforgettable ditties of the decade — something that was solidified after its placement in the oh-so-’90s teen rom-com She’s All That. "Kiss Me" peaked at number two on the Billboard Hot 100, but had great longevity — remaining on the chart for a whopping 35 weeks — so, swooning Lilith Fair crowds were witness to live performances of the song at the peak of its success.

'Foolish Games,' Jewel

Few things feel more ‘90s than then-newcomer Jewel Kilcher’s hauntingly poetic debut release, Pieces of You. While hits like “You Were Meant For Me” and "Who Will Save Your Soul" also climbed the charts, it was this gutting piano ballad that landed the Alaskan folk singer on both the 1998 Grammys stage and multiple Lilith Fair tour stops.

'If It Makes You Happy,' Sheryl Crow

Choosing a late-’90s Sheryl Crow gem is no easy feat, considering she was the reigning queen of raspy radio-rock hits at the time, but this carefree anthem is still one for the books. One of her top three highest-charting songs of all-time, after “All I Wanna Do” and “Strong Enough,” this Grammy-winning show of autonomy (and not giving a f--k) still holds up two decades later.

'Wide Open Spaces,' Dixie Chicks

Off country trio the Dixie Chicks’ fourth album, but their first with lead singer Natalie Maines, this title track is one of the highest-charting country songs of the lot — shooting to number one on both U.S. and Canadian country charts after its 1998 release. One of the most exciting new country acts on the Lilith Fair circuit, Dixie Chicks would go on to ignite controversy in their early-millennium career, and subsequently, great success.

'Sunny Came Home,' Shawn Colvin

A staple of any adult contemporary lover’s musical diet, “Sunny Came Home” is the most recognizable number from South Dakota songstress Shawn Colvin — breaking the top 10 of the Billboard Hot 100 and winning both record of the year and song of the year at the 1998 Grammy Awards. Alongside festival mastermind McLachlan, Colvin joined the tour for all three years of its late-’90s run.

'Kind and Generous,' Natalie Merchant

Another early onboarder to the Lilith Fair bandwagon was Merchant, whose 1998 album Ophelia followed her smash debut album Tigerlily (“Carnival,” “Wonder”), plus her split from the band 10,000 Maniacs. An immediately recognizable ‘90s hit, there’s no denying that the “Kind and Generous” chorus (“I’m bound to thank you for it”) kicked off some of the greatest Lilith Fair sing-alongs.

'Bitch,' Meredith Brooks

A timeless karaoke favourite, Meredith Brooks’ “Bitch” may have been her only huge song — but talk about going in and out with a bang. Joining the Lilith Fair tour in both 1997 and 1998, Brooks’ biggest single settled for nothing less than what it likely received during those years — approximately 30,000 voices screaming the B-word together, night after night.

Related links

Lilith Fair: 20 things you never knew for the festival's 20th anniversary

4 amazing Juno Awards moments from the '90s

The 50 best Canadian songs of the '90s