Songfacts®:

• Apple was a music prodigy and had been bashing out music on the piano since she was 11, but "Sleep To Dream" was the first song she wrote with a complete lyric - she wrote it when she was 14.
  
  Even at this young age, Apple was writing complex songs with very mature themes. She said of the song, "It's about an a--hole, an old boyfriend," but instead of trashing him in simple terms the way most 14-year-olds would, Apple eviscerates him with lines like:
  
  This mind this body and this voice cannot be stifled by your deviant ways
  So don't forget what I told you don't come around
  I got my own hell to raise
  
  It's not something Taylor Swift would write.
• Sleep has tormented Apple her whole life, and her insomnia often shows up in her songs, notably "Every Single Night" from her The Idler Wheel album. Apple often had nightmares, which explains why she didn't sleep to dream.
• This is the opening track on Tidal, Apple's debut album. The songs were written when she was still in high school; when she recorded them, she had never performed them live.
  
  Fiona was discovered through her demo tape, which found its way to Andrew Slater at Sony Records, who signed her and produced the album. On "Sleep To Dream," the drummer was Matt Chamberlain (ex-Pearl Jam) and the guitarist was Jon Brion, who later did production work for Apple.
• This was released as a single in April 1997, nearly a year after the Tidal album appeared. After an initial marketing push in 1996 that included a Saturday Night Live appearance and the release of her single "Shadowboxer," Apple went on simmer for a while, but picked up steam when she joined the Lilith Fair in the summer of 1997. "Sleep To Dream" didn't chart, but Apple's "Criminal" single, released in September, did, helping push Tidal to over 3 million in sales.
• The video, directed by Stephane Sednaoui, shows Apple in a kind of dream state, constantly shifting in time and space as she can't get comfortable. In September 1997, MTV named Apple Best New Artist In A Video for the clip at the VMAs. It was a defining moment for Apple, not because of the award, but because of her acceptance speech.
  
  Taking the podium, Apple explained that she didn't prepare a speech (she thought Hanson would win). She then launched into an extemporaneous description of exactly what was in her head. "This world is bulls--t and you shouldn't model your life about what you think that we think is cool and what we're wearing and what we're saying and everything," she told the stunned crowd. "Go with yourself."
  
  Apple later explained that by "this world," she meant the bubble of pomp and celebrity at the ceremony. Some felt she was ungrateful, but everyone agreed it was genuine. Apple got a surge of publicity, and her label responded by quickly releasing another single, "Criminal," which became her only Hot 100 hit, climbing to #21. The video for that song, showing Apple in a strange basement sharing space with young bodies in various states of undress, caused its own controversy. The notoriety goosed sales of Tidal, but took a toll on Apple's psyche. She soon became far less accessible, rarely appearing in public and releasing albums several years apart.