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===1966β1969: Early career=== At Kortchmar's urging, Taylor checked himself out of McLean and attended [[Elon University]] for a semester before he moved to New York City to form a band.<ref name="white-115"/><ref>{{Cite web |last=((Rocketman5000)) |date=2021-05-01 |title=Inside the Rock Era: James Taylor, the #46 Artist of the Rock Era Part One |url=https://top5000-rocketman5000.blogspot.com/2021/03/james-taylor-43-artist-of-rock-era.html |access-date=2024-08-28 |website=Inside the Rock Era}}</ref> They recruited Joel O'Brien, formerly of Kortchmar's old band [[King Bees (band)|King Bees]] to play drums, and Taylor's childhood friend Zachary Wiesner (son of academic [[Jerome Wiesner]]) to play bass. After Taylor rejected the notion of naming the group after him, they called themselves the Flying Machine.<ref name="time-cover-story"/><ref name="white-116">White, ''Long Ago and Far Away'', p. 116.</ref> They played songs that Taylor had written at and about McLean, such as "[[Knocking 'Round the Zoo]]", "Don't Talk Now", and "The Blues Is Just a Bad Dream".<ref name="bg112601"/><ref name="white-116"/> In some other songs, Taylor romanticized his life, but he was plagued by self-doubt.<ref name="nyt-palmer-1981"/> By summer 1966, they were performing regularly at the high-visibility Night Owl Cafe in [[Greenwich Village]], alongside acts such as [[the Turtles]] and [[Lothar and the Hand People]].<ref name="white-117">White, ''Long Ago and Far Away'', p. 117.</ref> Taylor associated with a motley group of people and began using heroin, to Kortchmar's dismay.<ref name="time-cover-story"/><ref name="white-117"/> In a late 1966 hasty recording session, the group cut a single, Taylor's "[[Night Owl (James Taylor song)|Night Owl]]", backed with his "Brighten Your Night with My Day".<ref name="white-118">White, ''Long Ago and Far Away'', pp. 118β119.</ref> Released on Rainy Day Records, distributed by [[Jubilee Records]], it received some radio airplay in the Northeast,<ref name="white-118"/> but only charted at {{numero|102}} nationally.<ref>{{cite web | url=http://www.acousticmusic.com/fame/p00456.htm | title=James Taylor and the Original Flying Machine β 1967 | author=Dexter, Kerry | publisher=Folk and Acoustic Music Exchange | year=1997 | access-date=December 26, 2008 | archive-date=October 10, 2008 | archive-url=https://web.archive.org/web/20081010210837/http://www.acousticmusic.com/fame/p00456.htm | url-status=live }}</ref> Other songs had been recorded during the same session, but Jubilee declined to go forward with an album.<ref name="white-118"/> After a series of poorly chosen appearances outside New York, culminating with a three-week stay at a failing nightspot in [[Freeport, Bahamas]] for which they were never paid, the Flying Machine broke up.<ref name="white-118"/> (A [[The Flying Machine (band)|UK band with the same name]] emerged in 1969 with the hit song "[[Smile a Little Smile for Me]]". The Flying Machine was briefly referenced in Taylor's song "[[Fire and Rain (song)|Fire and Rain]]", and following his success as a solo artist, the band's recordings were later released in 1971 as ''[[James Taylor and the Original Flying Machine]]''.) Taylor would later say of this New York period, "I learned a lot about music and too much about drugs."<ref name="nyt-palmer-1981">{{cite news | url=https://select.nytimes.com/search/restricted/article?res=F30611FB3A5D0C7B8CDDAD0894D9484D81 | title=Taylor: After the Turmoil and Wanderlust | author=[[Robert Palmer (American writer)|Palmer, Robert]] | newspaper=[[The New York Times]] | date=April 8, 1981 | access-date=February 9, 2017 | archive-date=March 14, 2022 | archive-url=https://web.archive.org/web/20220314172915/https://www.nytimes.com/1981/04/08/arts/the-pop-life-taylor-after-the-turmoil-and-wanderlust.html | url-status=live }}</ref> Indeed, his drug use had developed into full-blown [[heroin addiction]] during the final Flying Machine period: "I just fell into it, since it was as easy to get high in the Village as get a drink."<ref name="white-118"/> He hung out in [[Washington Square Park, New York|Washington Square Park]], playing guitar to ward off depression and then passing out, letting runaways and criminals stay at his apartment.<ref name="white-120">White, ''Long Ago and Far Away'', pp. 120β123.</ref> Finally out of money and abandoned by his manager, he made a desperate call one night to his father. Isaac Taylor flew to New York and staged a rescue, renting a car and driving all night back to North Carolina with James and his possessions.<ref name="white-120"/> Taylor spent six months getting treatment and making a tentative recovery; he also required a throat operation to fix vocal cords damaged from singing too harshly.<ref>White, ''Long Ago and Far Away'', p. 126.</ref> Taylor decided to try being a solo act with a change of scenery. In late 1967, funded by a small family inheritance, he moved to London, living in various areas: [[Notting Hill]], [[Belgravia]], and [[Chelsea, London|Chelsea]].<ref name="white-128">White, ''Long Ago and Far Away'', pp. 127β129.</ref> After recording some demos in [[Soho]], his friend Kortchmar gave him his next big break. Kortchmar used his association with the King Bees (who once opened for [[Peter and Gordon]]), to connect Taylor to [[Peter Asher]]. Asher was [[A&R]] head for [[the Beatles]]' newly formed label [[Apple Records]].<ref name="white-135">White, ''Long Ago and Far Away'', pp. 134β135.</ref> Taylor gave a demo tape of songs, including "[[Something in the Way She Moves]]", to Asher,<ref name=Asher>[https://www.youtube.com/watch?v=tDliZ42yoFA&list=PL78DA37F91244192E&index=5 "James Taylor & Carole King: Live at the Troubadour"] {{Webarchive|url=https://web.archive.org/web/20210315165330/https://www.youtube.com/watch?v=tDliZ42yoFA&list=PL78DA37F91244192E&index=5 |date=March 15, 2021 }}, 2007</ref> who then played the demo for Beatles [[Paul McCartney]] and [[George Harrison]]. McCartney remembers his first impression: "I just heard his voice and his guitar and I thought he was great ... and he came and played live, so it was just like, 'Wow, he's ''great''.'"<ref name="white-135"/> Taylor became the first non-British act signed to Apple,<ref name="white-135"/> and he credits Asher for "opening the door" to his singing career.<ref name=Asher/> Taylor said of Asher, who later became his manager, "I knew from the first time that we met that he was the right person to steer my career. He had this determination in his eye that I had never seen in anybody before."<ref name=Halperin/>{{rp|70}} Living chaotically in various places with various women, Taylor wrote additional material, including "[[Carolina in My Mind]]", and rehearsed with a new backing band.<ref name="white-136">White, ''Long Ago and Far Away'', pp. 136β137.</ref> Taylor recorded what would become his first album from July to October 1968, at [[Trident Studios]], at the same time the Beatles were recording ''[[The Beatles (album)|The White Album]]''.<ref name="white-136"/><ref>{{cite book | last=Lewisohn | first=Mark | author-link=Mark Lewisohn | title=The Beatles: Recording Sessions | publisher=[[Harmony Books]] | year=1988 | isbn=0-517-57066-1}} p. 146.</ref> McCartney and an uncredited [[George Harrison]] guested on "Carolina in My Mind", whose lyric "holy host of others standing around me" referred to the Beatles, and the title phrase of Taylor's "Something in the Way She Moves" provided the lyrical starting point for Harrison's classic "[[Something (Beatles song)|Something]]".<ref>{{cite news |last1=Kerns |first1=William |title=Legendary performer Taylor opens tour with intimate Lubbock concert |url=https://www.lubbockonline.com/story/entertainment/local/2016/04/09/legendary-performer-taylor-opens-tour-intimate-lubbock-concert/14921381007/ |access-date=March 8, 2023 |work=[[Lubbock Avalanche-Journal]] |date=April 9, 2016}}</ref> McCartney and Asher brought in arranger [[Richard Anthony Hewson]] to add both orchestrations to several of the songs and unusual "link" passages between them; they would receive a mixed reception, at best.<ref name="white-139">White, ''Long Ago and Far Away'', pp. 137β140.</ref><ref>{{cite web |url=http://www.beatles-discography.com/song-by-song/?s=something |archive-url=https://web.archive.org/web/20040603010101/http://www.beatles-discography.com/song%2Dby%2Dsong/?s%3Dsomething|title=Beatles songs β S |last=Cross |first=Craig |year=2004 |archive-date=June 3, 2004 |access-date=June 3, 2004}}</ref><ref name="rs-apple-review">{{cite news | url=https://www.rollingstone.com/artists/jamestaylor/albums/album/113822/review/5945820/james_taylor | archive-url=https://web.archive.org/web/20070602164839/http://www.rollingstone.com/artists/jamestaylor/albums/album/113822/review/5945820/james_taylor | archive-date=June 2, 2007 | title=Album Reviews: James Taylor | author=[[Jon Landau|Landau, Jon]] | magazine=[[Rolling Stone]] | date=April 19, 1969}}</ref> {{quote box|align=right|width=25em|bgcolor = Cornsilk|quote=James had been through so much by the time he was twenty that he had so much to express in his music. Other young artists of his age whom I worked with sang about how good or bad life was but really had no idea what they were singing about. James was already singing with the conviction of a singer much older than himself. Everything that he had already been through was evident in his songwriting.|source= β[[Peter Asher]], Taylor's manager<ref name=Halperin>Halperin, Ian. ''Fire and Rain: The James Taylor Story'', Citadel Press (2003)</ref>{{rp|66}}}} During the recording sessions, Taylor fell back into his drug habit by using heroin and [[methedrine]].<ref name="white-139"/> He underwent [[physeptone]] treatment in a British program, returned to New York and was hospitalized there, and then finally committed himself to the [[Austen Riggs Center]] in [[Stockbridge, Massachusetts]], which emphasized cultural and historical factors in trying to treat difficult psychiatric disorders.<ref name="white-142">White, ''Long Ago and Far Away'', pp. 142β144.</ref> Meanwhile, Apple released his debut album, ''[[James Taylor (album)|James Taylor]]'', in December 1968 in the UK and February 1969 in the US.<ref name="white-142"/> Critical reception was generally positive, including a complimentary review in ''[[Rolling Stone]]'' by [[Jon Landau]], who said that "this album is the coolest breath of fresh air I've inhaled in a good long while. It knocks me out."<ref name="rs-apple-review"/> The record's commercial potential suffered from Taylor's inability to promote it because of his hospitalization, and it sold poorly; "Carolina in My Mind" was released as a single but failed to chart in the UK and only reached {{numero|118}} on the U.S. charts.<ref name="white-142"/> In July 1969, Taylor headlined a six-night<!--TODO need cite on this --> stand at [[The Troubadour (Los Angeles)|the Troubadour]] in Los Angeles. On July 20, he performed at the [[Newport Folk Festival]] as the last act and was cheered by thousands of fans who stayed in the rain to hear him.<ref>{{cite web | url=http://www.wolfgangsvault.com/dt/james-taylor-fine-art-print/FFN690720-02-FP.html | title=James Taylor Fine Art Print | publisher=[[Wolfgang's Vault]] | access-date=December 26, 2008 | archive-url=https://web.archive.org/web/20090112144627/http://www.wolfgangsvault.com/dt/james-taylor-fine-art-print/FFN690720-02-FP.html | archive-date=January 12, 2009 | df=mdy-all }}</ref><ref name="cby-429">''Current Biography Yearbook 1972'', p. 429.</ref> His set at Newport was cut short after 15 minutes, when festival co-founder [[George Wein]] announced on stage that the [[Apollo 11]] astronauts had landed on the moon.<ref name="newport69">{{cite magazine |last1=Hodenfield |first1=Jan |title=Newport 1969 |url=https://www.rollingstone.com/music/music-news/newport-1969-71017/ |magazine=Rolling Stone |access-date=July 28, 2023 |date=August 23, 1969}}</ref> Shortly thereafter, Taylor broke both hands and both feet in a motorcycle accident on Martha's Vineyard and was forced to stop playing for several months.<ref name="white-144">White, ''Long Ago and Far Away'', p. 144β145, 147.</ref> However, while recovering, he continued to write songs and in October 1969 signed a new deal with [[Warner Bros. Records]].<ref name="white-144"/>
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