Her debut album, Tidal, containing songs written when she was in her teens, was released in 1996 and received a Grammy Award for Best Female Rock Vocal Performance for the single "Criminal".

Apple grew up in Morningside Gardens in Harlem[6] with her mother and sister, but spent summers with her father in Los Angeles, California.

[7] Apple later began to play along with jazz standard compositions after becoming proficient, through which she discovered Billie Holiday and Ella Fitzgerald, who became major influences on her.

[5][12] After the rape, Apple began attending Model Mugging classes, practicing self-defense,[11] but continued to suffer panic attacks while walking home from school, which led to her relocating to Los Angeles to live with her father for one year.

[12] The album sold 2.7 million copies and was certified three times Platinum in the U.S.[20][21] "Criminal", the third single, became a hit and the song reached the Top 40 on the U.S.

"[12] During this period, Apple also covered the Beatles' "Across the Universe" and Percy Mayfield's "Please Send Me Someone to Love" for the soundtrack of the film Pleasantville.

Its full title is a poem Apple wrote after reading letters that appeared in Spin regarding an article that had cast her in a negative light in an earlier issue.

When the Pawn, which was produced by Jon Brion, used more expressive lyrics, experimented more with drum loops, and incorporated both the Chamberlin and drummer Matt Chamberlain.

[citation needed] In a February 2000 set hampered by equipment issues to 3,000 audience members at the New York City Roseland Ballroom, a frustrated Apple left the stage without returning.

Apple sang with Johnny Cash on a cover of Simon & Garfunkel's "Bridge over Troubled Water" that ended up on his album American IV: The Man Comes Around and was nominated for a Grammy Award for "Best Country Collaboration with Vocals".

Recording sessions began in 2002, at Ocean Way Studios in Nashville, Tennessee, but later moved to the Paramour Mansion in Los Angeles.

Mike Elizondo, who had previously played bass on Pawn, was brought back as co-producer to complete the tracks he had begun with Brion and Apple.

[33] Despite suggestions that the album had caused a rift between Brion and Apple, they regularly perform together at Largo, a club in Los Angeles, including a joint appearance with Elizondo on bass just before the news broke of an official release.

It was eventually certified Gold,[20] though its singles ("Parting Gift", "O' Sailor", "Not About Love", and "Get Him Back") failed to enter any Billboard charts.

[39] Apple recorded a cover of "Sally's Song" for the 2006 special edition release of the soundtrack for the Tim Burton film The Nightmare Before Christmas.

Apple sang a cover of "(S)he's Funny That Way", composed by Neil Moret, lyrics by Richard Whiting, which is often associated with the singer Billie Holiday.

In June 2010, Apple released a song titled "So Sleepy", produced by Brion and written by children involved with the non-profit organization 826LA.

[43] In late 2010, Billboard published an article stating that Apple was planning on releasing a new album in spring 2011, with musician Michelle Branch claiming to have heard some of the new tracks.

[46] Apple delayed the album's release until 2012, explaining that she was waiting "until her label found a new president and that she didn't want her work to be mishandled amid corporate disarray.

[56][3] She subsequently gave an in-depth interview on Marc Maron's WTF podcast in July, in which she described her experience with obsessive–compulsive disorder throughout her adult life.

[57][58] Apple contributed a previously unreleased song entitled "Dull Tool" to the soundtrack of the 2012 Judd Apatow film This Is 40.

[60][61] In November 2012, Apple wrote a letter to her fans – a scan of which was posted to her website and her Facebook page – postponing the South American leg of her tour due to the health of her dog, Janet.

[62] In September 2013, a Chipotle ad appeared online with a soundtrack of Apple covering "Pure Imagination" from the 1971 film Willy Wonka and the Chocolate Factory.

[65] During 2014, Apple also appeared at a number of performances by Blake Mills, including in New York City and Cambridge, Massachusetts, during his tour in support of his second full-length album, Heigh Ho.

[68] In 2018, she joined Shirley Manson at the female-driven Girl School Festival in Los Angeles for a cover of "You Don't Own Me" by Lesley Gore, wearing a white T-shirt with "KNEEL, PORTNOW" written across it in ink.

[70] Apple was featured in the documentary and soundtrack for Echo in the Canyon with Jakob Dylan covering songs by artists such as the Beach Boys and the Byrds.

[78] On June 17, 2020, Apple was confirmed as an additional musician featuring on Bob Dylan's 39th album Rough and Rowdy Ways,[79] playing piano on the track "Murder Most Foul".

[90][91] According to Stephen Thomas Erlewine of AllMusic, "[Apple's] roots lay in jazz, show tunes, and classic '70s singer/songwriters, [a] blend that came into sharper focus on her second album, When the Pawn.

"[92] On June 30, 2019, Apple pledged to donate two years' worth of earnings from TV and movie placements of her song "Criminal" to the While They Wait fund, which assists refugees with basic necessities, immigration fees and legal services.

[94][95] In June 2020, Apple pledged to donate two years' worth of earnings from TV and movie placements of her song "Shameika" to the Harlem Children's Zone.