When Sarah McLachlan organized the first Lilith Fair traveling music festival in 1997, the concept was groundbreaking: three stages, dozens of performers…all of them women. Sarah had grown angry at the conventional concert promotion wisdom of the day, which stated that two female performers should never be featured back-to-back (because the audience would presumably lose interest). In 1996, she went against this advice and organized her own tour, which featured a new artist named Paula Cole. The tour was hugely successful, and the next summer she expanded this idea and Lilith Fair was born. The festival was so beloved by fans and critics that it returned in 1998 and 1999, with a reunion in 2010. The early Lilith Fair years coincided with a flood of hit songs and videos by female performers, causing music writers to claim that 1997 (and 1998) was the “Year of the Woman” in the music industry. The late 90’s was also the peak of the importance of the music video, and the Lilith Fair performers made their share of interesting clips to promote their songs.

Sarah McLachlan’s album Surfacing was released in the summer of 1997, just as the first Lilith Fair tour was picking up steam. The album was one of the biggest hits of the year, with four of its songs reaching the Top 40. Its first single, “Building a Mystery”, set the mood for not only the album, but the entire Lilith Fair experience: thoughtful lyrics, expressive singing, and the assurance that the listener was about to hear something amazing:

Shawn Colvin’s “Sunny Came Home” launched the somewhat obscure singer into the mainstream, landing in the top 10 and winning a Grammy award for song of the year. The song’s dark subject matter, about a woman who burns down her home in order to break with the past, went over the heads of many listeners on the radio, but was made obvious in the video:

Sheryl Crow’s album The Globe Sessions, her third, began with the single “My Favorite Mistake”. A story of heartbreak and betrayal, the song was rumored to be written about Sheryl’s ex-boyfriend Eric Clapton, although she has always denied this. The video was shot on vintage film, and featured Sheryl in her then-trademark leather pants, playing her favorite guitar:

“I Do” was the featured single from Lisa Loeb’s album Firecracker. At first listen, the song appears to be about a relationship, although Lisa eventually revealed that she directed the lyrics to her record company, who pressured her to write “radio-friendly” songs: “We were almost finished recording the album, Firecracker, and the record company told us that we still needed a single. I decided to write a song that sounded like a song about a relationship but was actually about the record company not ‘hearing’ a single on the record already. You can hear it in the lyrics, ‘You can’t hear it, but I do.’ The song ended up being an expression of strength and power even when someone’s not treating you right.” The video was a fixture on MTV:

Sixpence None the Richer had released quality music with little fanfare for half a decade before their single “Kiss Me” burst onto the scene in 1998. The band made two videos for the song; the second received a great amount of airplay on MTV and featured the band performing the song while sitting on a bench. The original video, however, was a tribute to the classic French film Jules et Jim:

When Natalie Merchant left the band 10,000 Maniacs in 1993, she immediately began to work on a solo album. Her hard work and eloquent lyrics served her well, and her 1998 album Ophelia became her biggest success yet. The single “Kind And Generous” reached the top 10 while Natalie was touring with Lilith Fair, proving how invaluable a spot on the tour had become by its second year of existence. The video featured Natalie as a member of a carnival: