Known for the songs "I Kissed a Girl" and "Supermodel," both of which were featured in the film Clueless from 1995.
She played guitar in a junior high school band. Her first album, Things Here Are Different, from 1990 was not a commercial success even though her producer was the legendary Todd Rundgren.
She used her album The Folk Years 2003-2003 to indulge her passions for standards such as Doris Day's "Que Sera Sera" and "Sunrise/Sunset" from Fiddler on the Roof, the classic Broadway musical.
Her music incorporated autobiographical aspects of her life and hearkened back to her Jewish heritage, her struggles with depression and anorexia, and the difficulties experienced by famous female celebrities.
She hesitated to accuse Katy Perry of plagiarism for popularizing a song in 2008 with the same title as her 1995 hit "I Kissed a Girl" even though the production of both songs was overseen by the same individual.