Fiona Apple is the daughter of singer Diane McAfee and actor Brandon Maggart. Her break into the music industry came in 1994, when she gave a demo tape of three songs to a friend who passed the tape along to producer and manager Andy Slater. Apple's rich alto voice, piano skills and lyrics got the attention of Sony Music executive Andy Slater, who signed her to a record deal. In 1996 Apple's debut album, Tidal, was released by Epic, a subsidiary of Sony. The album went on to sell 24 million copies and was certified eight times platinum in the U.S. "Criminal", the third single, became Apple's breakthrough hit. The song reached the top forty on the U.S. Billboard Hot 100, while the controversial Mark Romanek-directed music video became very popular on MTV. Other singles from Tidal included "Shadowboxer", "Slow like Honey", "Sleep to Dream", "The First Taste" and "Never Is a Promise". Her public image was tempestuous. She received the 1997 MTV Video Music Award for "Best New Artist" for "Sleep to Dream". During this period Apple contributed covers of The Beatles' "Across the Universe" and Percy Mayfield's "Please Send Me Someone to Love" to the soundtrack of the film Pleasantville.

Apple's second album, When the Pawn..., was released in 1999. Its full title is 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 Your Mind Is Your Might So When 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'll Know Where to Land and If You Fall It Won't Matter, Cuz You Know That You're Right. The title's length earned it a spot in the Guinness Book of Records for 2001. The album was cultivated during Apple's relationship with film director Paul Thomas Anderson. When the Pawn... received a positive reception from publications such as The New York Times and Rolling Stone. The album's lead single, "Fast as You Can", reached the top 20 on Billboard's Modern Rock Tracks chart and became Apple's first Top 40 hit in the UK. The videos for two follow-up singles, "Paper Bag" and "Limp" (directed by then-boyfriend Anderson), received very little play.

Apple sang with Johnny Cash on a cover of Simon and Garfunkel's "Bridge over Troubled Water" that ended up on Cash's album American IV: The Man Comes Around and was nominated for a Grammy Award for "Best Country Collaboration with Vocals". She also collaborated with him on Cat Stevens's "Father and Son", which was included on Cash's 2003 collection Unearthed.

Apple's third album, Extraordinary Machine, was originally produced by Jon Brion. In 2004 and 2005 tracks were leaked on the Internet in MP3 format and played on U.S. and international radio; subsequently, MP3s of the entire album, believed to have been produced by Brion, went online. Although a website distributing the album was quickly taken offline, they soon reached P2P networks and were downloaded by fans. A fan-led campaign, Free Fiona, was launched in support of the album's official release. In August 2005, the album was given an October release date. Production had been largely redone by Mike Elizondo, who had previously played bass on Pawn, and co-produced by electronica experimentalist Brian Kehew. The final mastering of Extraordinary Machine was performed by Brian Gardner. The released version has a far higher level of compression than any of Fiona’s previous releases. Extraordinary Machine became the highest-charting album of Apple's career in the U.S. on its release and was nominated for a Grammy Award for "Best Pop Vocal Album". It was eventually certified gold and sold 462,000 copies in the U.S., though its singles ("Parting Gift", "O' Sailor", "Not About Love" and "Get Him Back") failed to enter any Billboard charts. Apple went on a live tour to promote the album in late 2005, and from early 2006 supported Coldplay on their tour of North America.