1994–2001: Tidal and When the Pawn... Apple was introduced to the music industry in 1994, when she gave a demo tape containing the songs "
Never Is a Promise", "Not One of Those Times", and "He Takes a Taxi" to her friend who was the babysitter for music publicist Kathryn Schenker. Schenker then passed the tape along to
Sony Music executive Andy Slater. Apple's abilities captured his attention, and Slater signed her to a record deal. In 1996, Apple's debut album,
Tidal, was released by
Work Records and
Columbia Records. The record was largely inspired by Apple's recent breakup with her first boyfriend. "
Criminal", the third single, became a hit and the song reached the
Top 40 on the U.S.
Billboard Hot 100. The song's controversial
Mark Romanek-directed music video played on
MTV. Other singles from
Tidal included "
Shadowboxer", "
Sleep to Dream", and "Never Is a Promise". Apple accepted the
MTV Video Music Award for Best New Artist at the
1997 MTV Video Music Awards for her song "Sleep to Dream". During her acceptance speech she said: Apple responded to criticisms of her acceptance speech in
Rolling Stone in January 1998, stating, "When I have something to say, I'll say it." In 1997, Apple met director
Paul Thomas Anderson during a photoshoot, and the two began a relationship that lasted until 2002. Apple's second album,
When the Pawn..., was released in 1999. 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. The title's length earned it a spot in the
Guinness Book of Records for 2001. However, as of October 2007, it no longer has the longest album title, as
Soulwax released
Most of the Remixes, a
remix album whose title surpasses
When the Pawns length by 100 characters.
When the Pawn was cultivated during Apple's relationship with film director
Paul Thomas Anderson.
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. The album received a positive reception from publications such as
Rolling Stone. It did not fare as well commercially as her debut, though it was an
RIAA-certified
Platinum album After completing a
concert tour in support of her second album in 2000, Apple relocated to Los Angeles, where she still resides as of 2020.
2002–2010: Extraordinary Machine and release delays During her hiatus, Apple contemplated retiring from her recording career. 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". She also collaborated with Cash on
Cat Stevens's "
Father and Son", which was included in his 2003 collection
Unearthed. headquarters of
Sony BMG Music Entertainment in January 2005. Apple's third album,
Extraordinary Machine, was originally produced by
Jon Brion. In spring 2002, Apple and Brion, her longtime friend and producer on
When the Pawn, met for their weekly lunch meeting. Brion reportedly "begged" Apple to make another album. Apple agreed, and Brion went to Apple's label,
Epic Records, with strict stipulations (including no deadline), which the label eventually agreed to. Recording sessions began in 2002, at
Ocean Way Studios in Nashville, Tennessee, but later moved to the
Paramour Mansion in Los Angeles. Work on the album continued until 2003, and in May of that year it was submitted to Sony executives. 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 went online. Although a website distributing the album was quickly shut down, it soon reached
P2P networks and was downloaded by fans. Production had been largely redone "from scratch" by Elizondo and was co-produced by
Brian Kehew. Two of the 11 previous leaked tracks were relatively unchanged, and one new song was also included. 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.
Extraordinary Machine debuted at number seven and was nominated for a Grammy Award for "
Best Pop Vocal Album". It was eventually certified
Gold, Apple went on a live tour to promote the album. Beginning in the mid-2000s, Apple dated writer and television creator
Jonathan Ames. , 2006 In June 2006, Apple appeared on the joke track "Come Over and Get It (Up in 'Dem Guts)" by comedian
Zach Galifianakis. Galifianakis previously appeared in the music video for Apple's "Not About Love". 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. In May 2006, Apple paid tribute to
Elvis Costello on
VH1's concert series
Decades Rock Live!, by performing Costello's hit "I Want You". Her version was subsequently released as a digital single. Apple toured the East Coast during August 2007, with
Nickel Creek. In 2008, Apple recorded a duet titled "Still I" with Christophe Deluy. In 2009, Apple covered "Why Try to Change Me Now" and "I Walk A Little Faster" for
The Best Is Yet to Come – The Songs of Cy Coleman. In January 2010, Apple and Brion performed together at "Love and Haiti, Too: A Music Benefit", a charity concert for the people hurt by the
Haiti earthquake. 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. The song was included on a compilation album released by the organization titled
Chickens in Love. Apple collaborated with
Margaret Cho on her album
Cho Dependent, which was released on August 24, 2010.
2011–2018: The Idler Wheel..., tour, and legal troubles , New York, 2012 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. Drummer
Charley Drayton also told
Modern Drummer magazine that he was co-producing the record. However, the album was not released in the spring and
Billboard reported later that Epic was not aware of a record. 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." In January 2012, after its new record label head,
LA Reid hinted at new music from Apple, Epic Records announced that the album would be released later in the year. Apple announced performances at the
South by Southwest Festival and
a spring 2012 tour soon after.
The Idler Wheel..., Apple's fourth studio album, was released on June 19, 2012, in the United States. It became Apple's most successful album on the
Billboard 200, where it peaked at number three, and received critical acclaim. According to an article in
American Songwriter, "
The Idler Wheel isn't always pretty, but it pulses with life, brutal and true." While promoting
The Idler Wheel, Apple revealed in a June 2012 interview that she had briefly married an unnamed French photographer, later revealed to be
Lionel Deluy, "for complicated reasons" and had a passing liaison with a younger woman. On September 19, 2012, Apple was arrested at an
internal U.S. Border Patrol checkpoint in
Sierra Blanca, Texas, and charged with possession of
hashish, detaining her en route to a concert in
Austin, Texas, at the
Hudspeth County Jail. Apple contributed a previously unreleased song entitled "
Dull Tool" to the soundtrack of the 2012
Judd Apatow film
This Is 40. Another song was recorded for the film but was not used, ending up as the track "Cosmonauts" on her 2020 album
Fetch the Bolt Cutters. 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. According to the letter, the dog has
Addison's disease and has had a tumor "idling in her chest" for two years. 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. The video, which follows a scarecrow as he discovers the truth about
factory farming and processed food, was described as "haunted", "dystopian", "bizarre", and "beautiful". In 2014, Apple wrote the opening theme, "
Container", for the Showtime drama series
The Affair. 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. The pair first publicly collaborated on an acoustic version of Apple's song "I Know" in 2013. in 2012 on
The Idler Wheel... tour. Apple has collaborated with
Andrew Bird, and in 2016, she was featured in the song "Left Handed Kisses" from the album
Are You Serious. In September 2017, Apple played rarities at the Ohana Festival in
Dana Point, California. Also in 2017, she released "
Tiny Hands" for the
Women's March on Washington. 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. This was considered in response to Grammy head
Neil Portnow's heavily criticized comments that women need to "step up" to earn more Grammy nods.
2019–present: Fetch the Bolt Cutters In January 2019, Apple collaborated with
King Princess on a version of her 1999 song "I Know". The song was released for
Spotify's RISE program on January 25. 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. In November, she covered "Whole of the Moon," a
Waterboys song, for the series finale of
Showtime's
The Affair. In two
Instagram posts in March 2019, Apple hinted at the recording of a fifth album. In a September 2019 interview with
Vulture, she confirmed that the album was in its final stages, recorded with a band and planned for an early 2020 release. In a follow-up interview with
Vulture in January 2020, she said her new album would likely be out "in a few months." On March 8, 2020, Apple posted a video of herself
fingerspelling the phrase "M-Y-R-E-C-O-R-D-I-S-D-O-N-E". The album was met with widespread acclaim by music critics. At the
63rd Annual Grammy Awards, the album won
Best Alternative Music Album and the lead single "Shameika" won
Best Rock Performance. On June 17, 2020, Apple was confirmed as an additional musician featuring on
Bob Dylan's 39th album
Rough and Rowdy Ways, playing piano on the track "
Murder Most Foul". On April 15, 2021, Apple covered
Sharon Van Etten's "Love More", from the 10th anniversary of Van Etten's second album,
Epic. In December, she was featured on a cover of the Christmas classic "
Silent Night" released by
Phoebe Bridgers alongside her Christmas EP
If We Make It Through December. Apple joined with
Bear McCreary to perform his composition "Where the Shadows Lie", the end credits theme for "
Alloyed", the final episode of the first season of
The Lord of the Rings: The Rings of Power. The song features Apple singing the
Ring Verse, part of which is inscribed upon the
One Ring in
Black Speech. In March 2025, she featured on
The Waterboys' single, "Letter from an Unknown Girlfriend" from their album
Life, Death and Dennis Hopper. On April 25, 2025, Apple covered
Neil Young's "
Heart of Gold" as part of the tribute album
Heart Of Gold: The Songs Of Neil Young Volume I. On May 7, 2025, she released "Pretrial (Let Her Go Home)", a
protest song against the impact of
cash bail upon working-class families which was inspired by her time as a volunteer court watcher. ==Musical style and influences==