Sleep to Dream

The second single from Tidal, released on 25 February 1997, is reportedly Apple's first lyric, written when she was 14. Stéphane Sednaoui directed the video, which shows her singing in the rooms of an apartment while suffering from insomnia. Jon Brion plays guitars, vibraphone and tack piano, Matt Chamberlain drums and percussion, Dan Rothchild bass and Patrick Warren piano and Chamberlin. The song reached 28 on the Billboard Alternative Songs chart and 84 on the UK Singles Chart, her first entry there.

Pitchfork's Pelly wrote that Apple sounds eight feet tall on it and that it rumbles open with each word a drum. The Guardian heard a thundering bass drum and strings lending an undercurrent of unease to her sultry delivery. Kanye West called the line "I have never been so insulted in all my life" one of his favorite opening lines to a song, and Pelly reported that he said the song inspired him to rap as if from the top of a mountain. Macy Gray said she tried to cover it and found it did not work out of its mood.

On 4 September 1997 the video won Best New Artist in a Video at the MTV Video Music Awards, and Apple used her acceptance speech to say that the world was bullshit and to urge viewers to go with themselves. She recalled that backstage she was proud of herself and was given the silent treatment. A live version recorded at SXSW appears on the deluxe edition of The Idler Wheel..., and she performed the song on MTV Unplugged.