Natalie Merchant was lead singer and primary lyricist for the band 10,000 Maniacs, joining in its infancy in 1981 while she was a student at Jamestown Community College.

Natalie has said in interviews that after her split with 10,000 Maniacs she was so eager to begin writing her own material that she went home that very day and composed the song “I May Know The Word,” which was originally meant to appear on the soundtrack to the Tom Hanks movie, Philadelphia. The song was eventually cut from the soundtrack, but it would go on to appear on Merchant’s debut solo album, Tigerlily, which was released on Elektra in 1995. Merchant chose to name the album Tigerlily as she felt it captured the feel of the album, which she described as both “fierce” and “delicate.”

Seeking creative control, Merchant chose to fund Tigerlily herself, refusing the advance from the record company. She also wanted to work with a core-group of young musicians who she felt would be enthusiastic about the music. The group would consist of guitarist Jennifer Turner, bassist Barry McGuire, and former-Wallflower and eventual boyfriend to Merchant, Peter Yanowitz, who played drums on the album and who continued to do so with Merchant until their abrupt split in 2000.

Tigerlily was a critical and commercial success, spawning her first top-ten hit in the single Carnival, and achieving top-forty success with subsequent singles Wonder and Jealousy. The album would go on to sell nearly 5 million copies, and continues to be Merchant’s most successful album to date.

Three years passed before Merchant would release her sophomore solo effort, Ophelia. While Tigerlily contained a lot of sparse instrumentation, the music on Ophelia featured plenty of lush symphonic arrangements composed and conducted by British composer Gavin Bryers. Merchant treated the recording of Ophelia as a series of workshops, where she would invite a various musicians she had met over the years into her home studio to collaborate and record. In the end, 30 different musicians featured on the album, among them Brand New Heavies frontwoman N'Dea Davenport (with whom she duets on the song Break Your Heart, famed trumpet player Chris Botti, and the husband and wife duo, Don and Karen Perris, from the band The Innocence Mission.

While Ophelia is not a concept record in the traditional sense, the album-cycle saw Merchant flexing her creative muscles in surprising ways. The name of the album and the title track are a literary reference to Shakespeare's Ophelia, who in the play Hamlet becomes mad and eventually commits suicide. Merchant's Ophelia describes a woman who is also mad and suffering from what appears to be Multiple-Personality Disorder. The first single off the album was a happy and uncharacteristically simple song called Kind and Generous, which received massive airplay on VH1 and which solidified Merchant's role as a solo artist.

Merchant's next studio album on the Elektra label was Motherland, released in 2001. Motherland saw Merchant at her most experimental musically. Motherland achieved Gold on the Billboard charts after debuting at No. 30 on the Billboard 200 and No. 13 on the Top Internet Albums of 2001, retrospectively. Rolling Stone favored this album with 3 1/2 stars, and also noticed a difference in Merchant's voice, which was more deep and gritty than her previous albums.