Taylor's career began in the mid-1960s, but he found his audience in the early 1970s, singing sensitive and gentle songs. He was part of a wave of singer-songwriters of the time that also included Joni Mitchell, Tom Rush, Cat Stevens, Carole King, John Denver, Jim Croce, Don McLean, Gordon Lightfoot, and Jackson Browne, as well as Carly Simon, whom Taylor later married.
His 1976 album Greatest Hits was certified diamond and has sold more than 11 million copies. He has retained a large audience well into the 1990s and early 2000s, when some of his best-selling and most-awarded albums were released.
While living in New York City, Taylor became addicted to heroin. One night, after receiving a desperate phone call, his father drove to New York and rescued him. Taylor later wrote a song called "Jump Up Behind Me" that paid tribute to his father's help during a time of desperate need. The song also reflects on Taylor's memories of the long drive from New York City back to his home in Chapel Hill.
In 1968, Taylor moved to London. He was signed to Apple Records after sending a demo tape to Peter Asher (of Peter & Gordon) and released his debut album, James Taylor. Despite the Beatles connection, and the presence of Paul McCartney and George Harrison on one track, the album did not sell very well, and Taylor's addiction worsened. Moving back to the United States, Taylor checked into the Austen Riggs Center to treat his drug problem. Riggs is a hospital in Western Massachusetts in the town of Stockbridge (near where he lives today). By 1969 he was well enough to perform live, and had a six-night stand at the Troubadour Club in Los Angeles. On July 20, 1969 he performed at the Newport Folk Festival. Shortly thereafter he broke both hands in a motorcycle accident on Martha's Vineyard and was forced to stop playing for several months.
During the time Sweet Baby James was released, Taylor appeared with Dennis Wilson of The Beach Boys in a Monte Hellman film, Two-Lane Blacktop. Also, 1971 saw the release of Mud Slide Slim and the Blue Horizon, another hit album. He won a Grammy Award for his version of Carole King's "You've Got a Friend".
In 1972, Taylor returned with One Man Dog and married fellow singer-songwriter Carly Simon on November 3. His next album, 1974's Walking Man, was a disappointment but the following one, Gorilla, was a success partially because of a successful single cover version of Marvin Gaye's "How Sweet It Is (To Be Loved by You)." This was followed by In the Pocket in 1976 and then a greatest hits album that included some re-recordings of Apple Records-era material. It became a huge hit and remains Taylor's best selling album. It was certified diamond, and to date has sold over 11 million copies.
Taylor signed with Columbia Records and released JT in 1977 winning another Grammy Award for Best Male Pop Vocal Performance for his cover version of "Handy Man." The song "Traffic Jam" from the album has since become a favorite jingle for rush-hour radio traffic reports.
After collaborating with Art Garfunkel and briefly working on Broadway, Taylor took a two-year break, reappearing in 1979 with the cover-studded album Flag, featuring a Top 40 version of Gerry Goffin and Carole King's "Up on the Roof." Taylor also performed at the No Nukes concert in Madison Square Garden and appeared on the album and the film from the concert.
In the early 1980s Taylor's career was again beset by drug problems. Additionally, Taylor's wife, Carly Simon, was unhappy with his extended absences due to touring, as well as the ongoing drug abuse. After an ultimatum that he spend more time with their children, Taylor responded instead with the 1981 album Dad Loves His Work. He and Simon divorced in 1983.
He was quoted in various interviews that he was thinking of retiring after fulfilling his last contractual obligation, the Rock in Rio in 1985. However, he was surprised by the reception of the audience on Saturday, January 12 (there were 250,000 people, the biggest attendance of the 10-day festival), when he performed right before George Benson. Two days later, they were scheduled to perform in the same order, but because Taylor's extended performance had caused a delay to Benson's on Saturday, Benson proposed that they switch the order. Taylor ended up the finale in this second performance. Buoyed by the audience's reception, he decided to take back his life and his career. (Sixteen years later, on January 12, 2001, he played the very same site, at the opening night of the third Rock in Rio, whose organizer, Roberto Medina, described Taylor to the Brazilian press then as "his good luck charm.") The song "Only a Dream in Rio" was written in tribute to that night, with verses like "I was there that very day and my heart came back alive." The album, That's Why I'm Here, from which that song came, started a series of studio recordings that, while spaced further apart than his previous records, showed a more consistent level of quality and fewer covers.
In 1985 Taylor married, for the second time, to actress Kathryn Walker who helped him through recovery of his substance addictions. According to Taylor, he remains clean and sober to this day.
In 1988, he released Never Die Young. He began touring regularly. especially on the summer amphitheater circuit. His later concerts feature songs from throughout his career and are marked by the musicianship of his band and backup singers. The 1993 two-disc (LIVE) album captures this well, with a highlight being Arnold McCuller's descants in the codas of "Shower the People" and "I Will Follow." In 1995, Taylor performed the role of Lord in Randy Newman's Faust.
Taylor's two albums of original material from the 1990s were notably successful. His thirteenth album, New Moon Shine, went platinum in 1991 and he won the Grammy for Best Pop Album in 1998 for Hourglass.
Flanked by two greatest hit releases, October Road appeared in 2002 to a receptive audience. It featured a number of quiet instrumental accompaniments and passages. The album appeared in two versions, a single-disc version and a "limited edition" two-disc version which contained three extra songs including a duet with Mark Knopfler, "Sailing to Philadelphia," which also appeared on Knopfler's Sailing to Philadelphia album. Also in 2002, Taylor teamed with bluegrass musician Alison Krauss in singing "The Boxer" at the Kennedy Center Honors Tribute to Paul Simon. They later recorded the Louvin Brothers duet, "How's the World Treating You?" In 2004, after he chose not to renew his record contract with Columbia/Sony, he released James Taylor: A Christmas Album with distribution through Hallmark Cards.
Always visibly active in environmental and liberal causes, in October 2004 Taylor joined the "Vote for Change" tour playing a series of concerts in American swing states. These concerts were organized by MoveOn.org with the goal of mobilizing people to vote for John Kerry and against George W. Bush in that year's Presidential campaign. Taylor's appearances were joint performances with the Dixie Chicks.
In December 2004, Taylor appeared as himself in an episode of The West Wing entitled "A Change Is Gonna Come." He sang Sam Cooke's classic "A Change Is Gonna Come" at an event honoring an artist played by Taylor's wife Caroline. Taylor's rendition was then released over the Internet.
He appeared on CMT's Crossroads alongside the Dixie Chicks. In early 2006, Musicares honored Taylor with performances of his songs by an array of notable musicians. Before a performance by the Dixie Chicks, lead singer Natalie Maines acknowledged that he had always been one of their musical heroes, and had for them lived up to their once-imagined reputation of him.
In the fall of 2006, Taylor released a repackaged and slightly different version of his Hallmark Christmas album, now entitled James Taylor at Christmas, and distributed by Columbia/Sony.
On November 28–30, Taylor, accompanied by his original band and Carole King, headlined a series of six shows at The Troubadour. The appearances marked the 50th anniversary of the venue, where Taylor, King and many others, such as Tom Waits, Neil Diamond, and Elton John, began their music careers. Proceeds from the concert went to benefit the Natural Resources Defense Council, MusiCares, Alliance for the Wild Rockies, and the Los Angeles Regional Foodbank, a member of America's Second Harvest — The Nation's Food Bank Network. Parts of the performance shown on CBS Sunday Morning in the December 23 2007, broadcast showed Taylor alluding to his early drug problems by saying, "I played here a number of times in the 70s, allegedly..." Taylor has used versions of this joke on other occasions, and it appears as part of his One Man Band DVD and tour performances.
In December 2007 James Taylor at Christmas was nominated for a Grammy Award, but he did not win. In January 2008 Taylor recorded approximately 20 songs by others for a new album with a band including Luis Conte, Michael Landau, Lou Marini, Arnold McCuller, Jimmy Johnson, David Lasley, Walt Fowler, Andrea Zonn, Kate Markowitz, Steve Gadd and Larry Goldings. The resulting live-in-studio album, named Covers, was released in September 2008. Meanwhile, in summer 2008, Taylor and this band toured 34 North American cities with a tour entitled James Taylor and His Band of Legends.