As both Asher and the musicians discovered, reading Taylor wasn't always easy. Asher had to look for the smallest signs of any dissatisfaction, like the way Taylor might look grumpy at the end of a take but never articulate what he didn't like. “It would take a little digging to find out what should or could be changed,” Asher recalled. “You had to extract information from him.” Asher found Taylor a jumble of contradictions: quick-witted and intelligent, yet so gawky and nervous he didn't always look people in the eye when he spoke to them. At least Taylor wasn't spending prolonged, unexplained periods of time in the bathroom, as he had during the making of his first album. Given what Taylor had been through already, that alone felt like a significant victory to Asher.
Anyone who knew James Taylor knew he was a product, in equal doses, of music and isolation. When Taylor was three, in 1951, his familyâled by his father, Isaac, a doctor educated in Boston, and his mother, Trudyâhad returned to the state where Isaac was born, North Carolina. Isaac had accepted a job as an assistant professor at the University of North Carolina School of Medicine.
On the surface, their new home in Chapel Hill was idyllic: eight rooms, twenty-five acres, a hammock in the backyard. Music was everywhere. An upright piano took up residence in the living room; in the kitchen, the Taylor kidsâoldest brother Alex, followed by James, Livingston, Hugh, and Kateâwould pull out cans from the cupboards and break spontaneously into the jingles for each product. The children would sing sea shanties, Woody Guthrie songs, and sing-along favorites like “On Top of Old Smoky.” Thanks to Trudy, who'd studied voice at the New York Conservatory and had once trained with Aaron Copland at Harvard, the concept of a professional career in music wasn't unthinkable. James himselfâborn in Boston in 1948âtook cello lessons, briefly played in Chapel Hill's first Young People's Orchestra, and performed once with the North Carolina Symphony, playing the ballad “Blue Bells of Scotland.” Alex brought home Ray Charles and Bobby Blue Band records and joined a local bar band, the Corsairs.
The family summered on Martha's Vineyard in Gay Head and Chilmark, where James befriended Kortchmar. Hailing from Larchmont in Westchester County, just north of New York City, Kortchmar couldn't have been more different from Taylor: He was shorter, more extroverted, and gregarious, a born rock and roller even in his youth. During their first summer hanging out on the Vineyard, they realized they shared a mutual love of soul, R&B, and blues records. “That was so heavy to find someone else who was into that kind of music,” Kortchmar recalled. Kortchmar also learned his friend could sing when Taylor broke
into a Ray Charles song while they were hitchhiking. Before long, the two were playing at hootenannies on the Vineyard.
The tranquil settings masked a sense of unease and anxiety. Isaac had a drinking problem and was prone to go off on extended work trips, like the voyage to Antarctica that took him away from the family for nearly two years in the mid '50s. Trudy Taylor had to fend for herself, with sometimes unpleasant results (once she was stung by a swarm of bees while protecting her family). Isaac's isolation impacted on the family in deeper ways. Although Kate remained bubbly, Alex grew into the family rebel, the one always fighting with his parents. James was, according to his younger brother Livingston, “observant and fairly quiet, always held his cards close.” He could often be seen taking walks alone in the nearby woods. The sense that they were in the South but “of the North,” as James recalled, led him to feel isolated early; summers in Massachusetts only intensified those feelings. Even a hundred years after the Civil War, Taylor felt in his bones the difference between Southerners and, he recalled, “Yankees and outsiders,” and he was caught between them.
The mounting sense of disconnection inside him only grew after the family enrolled him in Milton Academy, a strict boarding school ten miles south of Boston, in the fall of 1961. Although he was returning to the state where his family had once lived, Taylor wasn't comforted by Milton's wide-open yards and brick buildings. As a teacher once recalled, he was hardly an “activist.” He tended to stay in his room and practice his new instrument, the guitar. When a rowdy classmate broke it, Taylor was fairly traumatizedâ“a bad moment for me,” he would later say. Although it was repaired, it never sounded the same.
When a depression set in around Thanksgiving of his senior year, the family pulled him out. “I had a shattered brain,” he recalled, leading to a stint at McLean Hospital, a $36,400-a-year Boston-suburb infirmary that, with its cottages and lawns, resembled a college campus. The sight of her older brother living in a locked ward so upset Kate that she broke
down during a visit. One day at dinner in an adjoining ward, he looked over and sawâor thought he sawâRay Charles. “I thought I was hallucinating,” he recalled. “It scared the shit out of me.” But his eyes didn't deceive him; Charles, who'd been sent to McLean after a heroin bust, was actually there. The sight of one of his heroes in the ward haunted him for decades.
After graduating from McLean's affiliated school, Taylor gravitated to New York City and its folk and blues clubs. His parents put up the money for his first apartment, on the Upper West Side, where he had only a mattress and a radio. With Kortchmar and another friend, drummer Joel O'Brien, he formed a band, the Flying Machine; later, he and O'Brien relocated to the Hotel Albert on East 10th Street, home base of Tim Buckley, the Lovin' Spoonful, and others whose music spilled out of Village clubs nearly every night. The band landed gigs at some of those spots, particularly the Night Owl, and Taylor's songwriting began to blossom with songs like “Night Owl,” which alluded to his dark side. Like his physique, his singing voice was sturdy and stoic, with an underlying ruggedness.
Although the Flying Machine recorded a few of its songs, the band struggled, barely taking in $10 a night at clubs. By then, Taylor had discovered heroin. “My family has a history of addiction,” he recalled, “and I'm probably genetically predisposed to substance abuse. So I didn't stand a chance. Those drugs, powerful drugs, were as available as a beer at the bar. The places I was living, the people I was spending time withâeverybody was experimenting with everything all the time. So it was just a matter of time. There wasn't as much information available about what it meant to be getting high and how addictive things were. You still thought you could take some drugs and not get addicted to them.”
Taylor was wrong, of course. Once again, his body crashed, and Isaac drove up to New York to haul his drug-addled son back home to North Carolina. “Sort of to lick my wounds a little bit,” James later said. He
was only home about nine months before he left againâthis time for London, again with funding from his parents. Only nineteen, Taylor arrived in the city in late 1967. At first he lived with a friend of the family's from the Vineyard who had a place in Manhattan; later, his duffel bag became his home. By coincidence, Kortchmar had a contact in London. Several years before, one of Kortchmar's bands, the King Bees, had played behind Peter and Gordon. Kortchmar heard Asher was now working at Apple and was in charge of signing acts. Kortchmar didn't think Taylor would actually call Asher; his friend already seemed battered by his experiences in life and the music business. But Kortchmar also knew Taylor was capable of doing the unexpected.
Wearing a black suit with a yellow tie, Paul McCartney arrived at the Apple office on Baker Street in the early months of 1968 to chair a meeting. The Beatles' attempt to control their destiny after the death of their manager, Brian Epstein, Apple was a multi-legged beastâpart record company, boutique, film studio, electronics company, and any other whim that came to mind. Also in the meeting was Asher, newly appointed as Apple's A&R man. Asher's connections with McCartney ran deep. Although he'd begun by singing protest songs in clubs at fifteen, he made a name for himself as one half of Peter and Gordon with his friend Gordon Waller. By chance, Asher's sister Jane was dating McCartney, and when another British act, Billy J. Kramer, rejected a new McCartney song called “A World Without Love,” Peter and Gordon eagerly recorded it and turned a reject into a number one American hit.
Although the duo crashed the charts a few more times, Asher tired of touring and making too little money. When the Apple offer came along, Asher, a courtly and friendly type, was more than ready to make the switch to talent scout. At this particular meeting, he brought with him a
tall, gangly man who sat in a chair against the wall, saying nothing and cracking his knuckles. When the meeting broke, McCartney, Asher, the stranger, and a few employees adjourned to a nearby pub, where Asher finally told everyone who the kid wasâJames Taylor, an American musician whom Asher wanted to sign to the label.
“Peter says your songs are very good,” McCartney told him.
“Well, uh, I don't know,” Taylor stammered. “I hope they are.”
Asher had met Taylor only a month or two before, when Taylor called him at his apartment on Marylebone High Street and asked if he could drop off his demo tape, which included songs like “Something in the Way She Moves” (which inspired George Harrison's “Something”) and “Knocking 'Round the Zoo.” When Taylor showed up, Asher welcomed him into the apartment he shared with his girlfriend Betsy and played Taylor's acetate, which impressed him. To Taylor's relief, Asher allowed him to live at the apartment for a whileâand, even better, told him McCartney had liked his songs and had received permission from the other Beatles to make Taylor Apple's first signed artist. Despite his own self-destructive tendencies, Taylor was suddenly the proud owner of a three-year record deal with the most talked-about new label in the business. “I was signed before I knew what was happening,” he recalled. “It was really a remarkable turn of events. I was this huge Beatles fan and I definitely landed on my feet in a great position.”
Like so many situations before in his life, this one began with nothing but promise. While awaiting the chance to begin making his record, he became friendly enough with the Beatles to be able to drop by and hear the first playback of “Hey Jude” and watch them work on “Revolution.” At Asher's house in the Surrey countryside, he'd sit alone in an empty pool and play and sing. He'd claim he wanted to be alone, but in doing so, drew attention to himself anyway. In July 1968, Taylor and Asher began Taylor's album, using Trident Studio whenever the Beatles weren't working there; McCartney dropped by to play bass and
sing harmonies on one song, “Carolina in My Mind,” and Harrison also, according to Taylor, sang an uncredited part on the same song. (The “holy host of others standing around me” in the lyric was Taylor's nod to the Beatles.)
Released in the U.K. first, in 1968,
James Taylor
revealed a songwriter with a graceful gift for melody and musicality. The best of its songsâ“Carolina in My Mind,” “Rainy Day Man,” “Brighten Your Night with My Day”âfelt instantly familiar and ingratiating, not unlike McCartney's sharpest moments. Taylor's skills as a guitaristâthe crisp-air, pulled-string fingerpicking style that would become his trademarkâannounced themselves on a version of the traditional ballad “Greensleeves”; typical singersongwriters normally couldn't play with such jazz-influenced syncopation.
At the same time, anyone who scoured the lyric sheet also noticed a songwriter grappling with multiple issues. “Something's Wrong” hinted at his aimless life, while “Knocking 'Round the Zoo,” which dated back to the Flying Machine days, detailed Taylor's stay at McLean. (“There's bars on the windows and they're counting up the spoons,” he sang, if somewhat drolly.) The songs mentioned pain and sadness and, far less convincingly, sunshine and solace.
James Taylor
was the sound of a man grappling with somethingâand Asher's production couldn't seem to figure it out either. Sometimes, as on “Something in the Way She Moves,” Asher was savvy enough to know Taylor's voice and guitar would suffice. Other songs were unnecessarily gussied up with bassoons, harpsichords, string sections, and horns. In the way the arrangements worked hard to liven up the songs, Asher's production, which was designed to draw attention to his act, was a study in denial.