Apple is the daugher of singer Diane McAfee and actor Brandon Maggart. As a child she was believed to be anti-social and as a result received psychotherapy. At the age of 12 she was the victim of a sexual assault. She attended high school in Los Angeles where she recorded a demo tape. The tape found its way to a record executive through his babysitter, a friend of Apple's. Her 1996 debut album Tidal with its hit song "Criminal" was released to huge popularity and critical acclaim. It eventually went on to sell millions of copies.
Apple's public persona began to overshadow her music. In particular, while accepting an MTV music video award, she chided the audience for worshipping celebrity culture. She dismissed it as "bullshit" and cursed up a storm, eventually quoting Maya Angelou: "Go with yourself." This backfired on her as she was viewed as hypocritical. Detractors wanted to know how she could parade in her underwear in a music video that obviously reflected pornography only to turn around and tell young women to ignore it. In particular, comedienne Janeane Garofalo delivered a scalding parody of the awards show speech: "This world is bullshit; even though I'm skinny and appear in a music video wherein I am in my underwear, and even though I'm maybe not the most talented singer, songwriter or, whatever...go with yourself." It purportedly left Apple in tears. She vowed to intentionally make herself less pretty to counteract the pressure on young women to be beautiful.
During a relationship with magician David Blaine Apple wrote and recorded her 1999 second album. Its full title was When the Pawn Hits the Conflicts He Thinks Like a King; What He Knows Throws the Blows When He Goes to the Fight, and He'll Win the Whole Thing 'Fore He Enters the Ring - There's No Body to Batter When the Mind Is Your Might, So You Go Solo, You Hold Your Own Hand and Remember That Depth Is the Greatest of Heights, and If You Know Where You Stand, Then You Know Where to Land, and If You Fail It Won't Matter Cuz You'll Know That You're Right. The title is often shortened to When the Pawn.
Critics immediately dismissed the album, many without hearing it. The initial review in Spin Magazine simply quoted the title, and then underneath read "Whoops. Now we don't have room for a review. One star." The album's sound was more mature both musically and lyrically, but it did not fare as well commercially. Although several singles were released, the videos received very little airplay. Many critics eventually heralded the material as a musical achievement, but the pomp and ego surrounding her public appearances (and the lengthy title) made it inaccessible to many listeners. The album's lyrics were also often difficult to decipher due to Apple's usage of archaic and intellectual words in place of layman's terms, for example: "My derring-do allows me to dance the rigadoon around you. But by the time I'm close to you I lose my desideratum [..]"
Apple is currently working on her third album, tentatively titled Extraordinary Machine, along with Jon Brion, producer of When the Pawn. The album's release, originally set for September 2003, is expected to be in mid-2004, almost two years after work began.