At 16, Elisa met Caterina Caselli, who one year later signed her to the record company Sugar. At 18 she left for Berkeley, California (U.S.) to work on songs for her debut album with record producer Corrado Rustici, who has also worked with Whitney Houston, Aretha Franklin and Zucchero among others.
Elisa's first single "Sleeping in Your Hand" was released in late May 1997, followed by her debut album Pipes & Flowers on September 22. She was credited as a writer or co-writer on all tracks. The album soon went quadruple platinum in Italy and won her two prizes: Targa Tenco and PIM (Premio Italiano della Musica). She was also a special guest on Eros Ramazzotti's European tour. In 1998, the re-release of Pipes and Flowers included a new track, Cure Me, recorded in Venice with British producer Darren Allison.
Main article: Asile's World
May 5, 2000 saw the release of Asile's World (Asile being Elisa written backwards). The album took a new turn in terms of musical influences and featured songs produced by Howie B, Roberto Vernetti, Mauro Malavasi and Leo Z.
In September 2000 Elisa recorded her first song in Italian, "Luce (Tramonti a nord est)". The song was initially written in English, but an Italian lyric was written in collaboration with fellow singer Zucchero. The song was performed at the 2001 Sanremo Festival supported by the Solis String Quartet, and won her the Critics' Award, Interpreter of the Year as well as the competition altogether. Both Italian and English versions were later included in a re-release of Asile's World. In November she was awarded three prizes at the Italian Music Awards: Best female artist, Best single (Luce) and Best song, as well as taking home the Best Italian Artist at the MTV Europe Music Awards 2001 in Frankfurt. She also received Premio Italiano della Musica's Best Female Artist and Best Single (Luce).