In 1963, his parents sent him to the Milton Academy, a prep school in Massachusetts. That summer, he met fellow guitarist Danny "Kootch" Kortchmar while staying on Martha' s Vineyard, and the two formed a folk duo. Taylor dropped out of school at 16 to form a band with his brother Alex, called The Fabulous Corsairs.
Often moody and depressed, James committed himself to the McLean Mental Institution in Massachusetts when he was just 17 years old. After a nine-month stay, he returned to New York in 1966 and formed a new group, with Kortchmar and Joel O'Brien. The band played in Greenwich Village and was signed to a fledgling record label, Rainy Day Records. They released one single, "Brighten Your Night With My Day" / "Night Owl," both songs written by Taylor. The record went nowhere, and the band broke up in the spring of 1967.
At 18, now being supported by his parents in his own apartment, the seemingly affluent James drew the predictable crowd of hangers-on and emotional parasites. He experimented and soon was addicted to heroin. He had the drive to move out, and after several months of travelling he arrived in London and found a flat in Notting Hill (which in 1968 was hardly the place for someone trying to kick a drug habit!). Once again 'Kootch' came to the rescue, and suggested Taylor take a demo tape to Peter Asher. 'Kootch' had supported Peter And Gordon on an American tour, and Asher was now looking for talent as head of the new Apple Records.
Both Asher and Paul McCartney liked the music and the thin, weak and by now world-weary teenager was given the opportunity to record. The resulting album called simply "James Taylor", was released in the U.K. in December 1968 and in the U.S. in February 1969. It received little attention. A more pressing concern, however, was that Taylor had not been able to kick heroin. As a result, he returned to the U.S. and checked into the Austin Riggs Hospital in Massachusetts. By July 1969, he had recovered sufficiently to make his solo debut at the Troubadour nightclub in Los Angeles, but soon after he was in a motorcycle accident and broke both of his hands, which put him out of commission for several months.
Meanwhile, Asher, frustrated at the disorganized Apple, moved to America. Once free of his Apple contract, he secured a deal with Warner Brothers Records and rounded up a team of supportive musician friends; 'Kootch', Leland Sklar, Russ Kunkel and Carole King. Their first album, "Sweet Baby James" was released in February, 1970 and featured the single "Fire and Rain," a song that reflected on James' experiences in mental institutions.
The single peaked in the top five in October, the same month that "Sweet Baby James" would start a two year stay on the U.S. album charts. With that, interest in Taylor's first album was re-stimulated, and it also reached the charts, along with the single "Carolina On My Mind". "Sweet Baby James" then spawned a second single, "Country Road", which peaked in the Top 40 in March 1971. The same month, Taylor appeared on the cover of Time magazine, touted as the founder and leading proponent of the "singer/songwriter" trend in popular music.
Now free of drugs, Taylor acted in a cult drag-race film called "Two-Lane Blacktop", co-starring with the Beach Boys' Dennis Wilson. It was not successful, and Taylor never pursued an acting career, though it has been well-reviewed subsequently. Taylor also worked on a new album, returning to record stores in April 1971 with "Mud Slide Slim and the Blue Horizon". As he toured the U.S., the LP spent the summer in the Top Ten, eventually peaking at number two, paced by its first single, "You've Got a Friend," written by Carole King. The song hit number one in July and went gold, followed by a second single, "Long Ago and Far Away," that reached the upper Top 40. On March 14th, 1972, James won the 1971 Grammy for "Best Pop Vocal Performance, Male", for "You've Got a Friend".
Taylor took more than a year and a half to release his next album, "One Man Dog", which contained another hit, "Don't Let Me Be Lonely Tonight". Fortunately, Taylor was not lonely for long. On November 3rd, 1972, during an appearance at Radio City Music Hall in New York, he announced to the crowd that he had married singer/songwriter Carly Simon earlier in the day. Simon was already well known for the hits "That's The Way I've Always Heard It Should Be" and "Anticipation", and would soon top the charts with a song called "You're So Vain".
The newly weds duetted on a version of the Charlie And Inez Foxx hit, 'Mockingbird', which made the U.S. Top 5 in 1974 and went gold. That spring, Taylor launched a major tour in anticipation of his next album, "Walking Man", released in June. Though it reached the Top 20, the album was a commercial disappointment, failing to go gold or produce a chart single. But Taylor bounced back the following year with the May release of "Gorilla". Again, he succeeded by reviving an old hit, this time Marvin Gaye's 1964 song "How Sweet It Is (To Be Loved by You)", which reached the Top Five, helping the album become a Top Ten, gold-selling hit. Taylor was also displaying confidence and sparkling onstage wit, having a superb rapport with his audiences, where once his shyness was excruciating.
Taylor's seventh album, "In the Pocket", appeared in June 1976. The first single was the singer's own "Shower The People" which reached the Top 40, while the album made the Top 20 and went gold. Nearing the end of his Warner Bros. contract, Taylor re-recorded a couple of his Apple songs for his Greatest Hits LP. With that, he bolted to Columbia Records. His debut for the label, "JT", was released in June 1977.
Once again, the singer/songwriter found success with someone else's material when he covered Jimmy Jones' 1959 song, "Handy Man" and took it into the top five, followed by a top 20 showing for his own "Your Smiling Face". With such stimulation, "JT" reached the top five and sold over two million copies. On February 23rd, 1978, Taylor picked up a second Grammy for "Best Pop Vocal Performance, Male", for "Handy Man".
Along with Paul Simon, Taylor was a featured singer on Art Garfunkel's cover of "(What A) Wonderful World", previously a hit for Sam Cooke and Herman's Hermits, which peaked in the Top 20 in March 1978. Taylor next became involved with the Broadway musical "Working", based on Studs Terkel's bestseller, writing three songs for it. The show ran a scant 25 performances after opening on May 14th, 1978, but Taylor reclaimed the songs, "Millworker" and "Brother Trucker" for his next album. Meanwhile, his duet with wife Carly Simon on a revival of the Everly Brothers' "Devoted to You" barely reached the Top 40 in September.
Taking a nearly two-year break between albums, "Flag" appeared in April 1979, its Top 40 hit single being a revival of the 1963 Drifters hit "Up on the Roof". Despite the lack of a really big hit single, the LP reached the Top Ten and went platinum. That September, Taylor performed at Madison Square Garden in the No Nukes concerts, later being featured in the No Nukes triple-LP and in the No Nukes concert film.
In the summer of 1980, despite not having a current album to promote, Taylor embarked on a national tour. From here on, recurrent touring became a regular part of his career and contributed to his longevity as an artist. That fall, he appeared on the children's album "In Harmony 2", singing "Jelly Man Kelly". The album won the 1981 Grammy for Best Recording for Children. He toured extensively during 1981, releasing "Dad Loves His Work" in February. The album reached the Top Ten and went gold, spurred by the Top Ten success of the single "Her Town Too", written by Taylor, J.D. Souther, and Waddy Wachtel, Taylor's most successful original composition since "Fire and Rain".
The constant touring and time away from home took its toll on his family life. After ten years, his marriage to Carly Simon came to an end in 1983. James took it in stride and continued on. In January 1985, he performed at the Rock in Rio concert in Brazil, a show that resulted in the Brazil-only release "Live in Rio". His next studio album, following a gap of more than four years, was "That's Why I'm Here", released in October 1985. As usual, his record label issued a cover song as the single; in this case it was Buddy Holly's "Everyday", which barely cracked the Top 100. Nevertheless, Taylor's long career and constant touring had brought him a permanent audience ready to buy his records, and the album eventually went platinum. On December 14th, 1985, he married for the second time, to Kathryn Walker; a month later, he was on tour in Australia.
Road work continued to be Taylor's primary occupation in the mid-'80s, but he came off tour long enough to finish another album, "Never Die Young" Only a little more than two years after, "That's Why I'm Here", was released in January 1988. The title song, issued as a single, barely reached the charts, but the album was another million-seller. The late '80s and early '90s saw more extensive, worldwide touring. "New Moon Shine", Taylor's 13th regular album release, came in October 1991, featuring the top 40 single, "Copperline", the same month that he sold out six consecutive shows at the Paramount Theater in New York. The disc stayed on the charts nearly a year and sold a million copies.
Despite his consistent draw as a concert attraction, Taylor had never released a live album in the U.S. until the August 1993 appearance of 'James Taylor Live', a two-CD set that went platinum within months. Columbia Records, which never had a Taylor compilation to promote, trimmed the album down to a single disc of hits for the 1994 release, "Best (Live)".
In 1995, James once again shared the stage with Carly Simon, in front of 10,000 fans on Martha’s Vineyard, Massachusetts. It was the first time they appeared live on the same stage since 1979. The former couple played their own solo sets before combining their efforts in raising money for the local agricultural society.
James was divorced from his second wife, Kathryn, in 1996. His next album, "Hourglass", released in May 1997, demonstrated his continuing appeal, reaching #9 on the Billboard Hot 200, Taylor's first Top 10 album in sixteen years. On February 25, 1998, it won the 1997 Grammy for Best Pop Album.
Taylor's first "Greatest Hits" album earned him the RIAA's newly-created Diamond Award, given for sales in excess of 10 million units in the United States. For his extraordinary achievements, James Taylor has been honoured with the 1998 Century Award, Billboard magazine's highest accolade, bestowed for distinguished creative achievement. The year 2000 saw James Taylor's induction to the Rock and Roll Hall of Fame and the Songwriters' Hall of Fame.
Taylor's Platinum-certified "October Road" appeared in 2002 to positive reviews. Later that year, he paired up with Bluegrass musician Alison Krauss in singing "The Boxer" at the Kennedy Center Honors Tribute to Paul Simon.
In 2004, James appeared with The Dixie Chicks playing a series of concerts in America with the goal of convincing people to vote for John Kerry and against George W. Bush in that year's Presidential campaign. On October 24th of that year, he sang "The Star-Spangled Banner" at Game 2 of the World Series in Boston. That December, he appeared as himself in an episode of the TV show The West Wing where he sang Sam Cooke's "A Change Is Gonna Come".
Autumn, 2006, brought a repackaged version of his holiday album, now entitled "James Taylor at Christmas". That same year, Taylor performed Randy Newman's song "Our Town" for the Disney animated film Cars. The song was nominated for the 2007 Academy Award for the best Original Song. On January 1st, '07, Taylor headlined the inaugural concert at the Times Union Center in Albany, New York, honoring newly sworn in Governor of New York Eliot Spitzer.
Taylor's next album, "One Man Band" was issued on CD and DVD in November, 2007 on Starbucks' Hear Music Label. The introspective album grew out of a three-year tour of the United States and Europe and featured some of Taylor's most beloved songs. Later that same month, Taylor, accompanied by his original band and Carole King, headlined a series of six shows at The Troubadour to mark the 50th anniversary of the venue.
In October, 2008, Taylor performed a series of free concerts in five North Carolina cities in support of Barack Obama's presidential bid. On January 18th, 2009, he performed at the We Are One: The Obama Inaugural Celebration at the Lincoln Memorial, singing "Shower the People" with John Legend and Jennifer Nettles of Sugarland. On May 29th of '08, James became the final musician to appear on Jay Leno's original 17-year run on The Tonight Show.
On January 1st, 2010, Taylor sang the American national anthem at the NHL Winter Classic at Fenway Park in Boston. In March of that year he kicked off the Troubadour Reunion Tour with Carole King and members of his original band for shows in Australia, New Zealand, Japan and North America. That set of shows grossed over $59,000,000. On September 11th, 2011, Taylor performed "You Can Close Your Eyes" in New York City at the National September 11 Memorial & Museum for the 10th anniversary of the 9/11 attacks.
The Spring of 2012 was booked with shows in Europe and the Summer months had James on tour in Canada and the United States.