"Sleep to Dream" is a song written and recorded by American alternative singer-songwriter Fiona Apple. It was released on April 14, 1997 by Work Records and Columbia Records as the second single from her debut studio album Tidal (1996).

The song's accompanying music video was filmed by French director Stéphane Sednaoui and received positive reviews. Apple won the MTV Video Music Award for Best New Artist in a Video in 1997, in which it garnered worldwide controversy after she proclaimed during her acceptance speech: "This world is bullshit, and you shouldn't model your life about what we think is cool, and what we're wearing and what we're saying." Despite entering on a single Billboard chart, the song remains one of Apple's most successful singles to date.

"Sleep to Dream" was reportedly Apple's first lyric, penned when she was 14. She recorded the song with collaborator Jon Brion in 1995 immediately after being signed to a record deal with Sony Music Entertainment. It was later released as the third single from Tidal. Apple performed "Sleep to Dream" in various events, notably on the television special MTV Unplugged: Fiona Apple. A live version recorded at the SXSW appears on the deluxe version of Apple's fourth studio album, The Idler Wheel... (2012).

The song peaked at number 34 on the Billboard Alternative Songs chart on the week ending April 26, 1997 and spent 13 weeks there. It also peaked at number 84 on the UK Singles Chart (number 79 on the compressed chart, with exclusions below number 75), becoming Apple's first song to chart in the United Kingdom. "Sleep to Dream" has also received critical acclaim from music critics. Christopher John Farley of TIME wrote: "In "Sleep to Dream", she assumes a smoldering anger that comes off like a muted Alanis Morissette."People Magazine also remarked: "A sort of hybrid of Alanis Morissette and Nina Simone—part rebellious rocker and part sultry jazz singer—Apple comes on tough in songs like "Sleep to Dream," a slow, smoldering tune in which she kisses off a reluctant lover ("You say love is a hell you cannot bear/And I say gimme mine back and then go there, for all I care")."

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