James Taylor Biography
Taylor achieved his major breakthrough in 1970 with the #3 single "Fire and Rain" and had his first #1 hit the following year with "You've Got a Friend", a cover of Carole King's classic song. His 1976 Greatest Hits album was certified Diamond and has sold 12 million US copies. Following his 1977 album, JT, he has retained a large audience over the decades. His commercial achievements declined slightly until a big resurgence during the late 1990s and 2000s, when some of his best-selling and most-awarded albums (including Hourglass, October Road and Covers) were released.
James Taylor was born at Massachusetts General Hospital in Boston, Massachusetts, on March 12, 1948, where his father, Isaac M. Taylor, was a resident. His father was from a well-off family of Southern Scottish ancestry. His mother, the former Gertrude Woodard, had studied singing with Marie Sundelius at the New England Conservatory of Music and was an aspiring opera singer before the couple's marriage in 1946. James was the second of five children, the others being Alex (born 1947), Kate (born 1949), Livingston (born 1950), and Hugh (born 1952).
In 1951, when James was three years old, the family moved to the countryside of Carrboro, North Carolina, when Isaac took a job as Assistant Professor of Medicine at the University of North Carolina School of Medicine. They built a house in the Morgan Creek area, which was sparsely populated. James would later say, "Chapel Hill, the piedmont, the outlying hills, were tranquil, rural, beautiful, but quiet. Thinking of the red soil, the seasons, the way things smelled down there, I feel as though my experience of coming of age there was more a matter of landscape and climate than people." James attended public primary school in Chapel Hill. Isaac's career prospered, but he was frequently away from home, either on military service at Bethesda Naval Hospital in Maryland or as part of Operation Deep Freeze in Antarctica during 1955–1956. Isaac Taylor later rose to become Dean of the UNC School of Medicine from 1964 to 1971. The family spent summers on Martha's Vineyard beginning in 1953.
Taylor first learned to play the cello as a child in North Carolina, and switched to the guitar in 1960. His style on that instrument evolved from listening to hymns, carols, and Woody Guthrie, while his technique derived from his bass clef-oriented cello training and from experimenting on his sister Kate's keyboards: "My style was a finger-picking style that was meant to be like a piano, as if my thumb were my left hand, and my first, second, and third fingers were my right hand." He began attending Milton Academy, a prep boarding school in Massachusetts in Fall 1961; summering before then with his family on Martha's Vineyard, he met Danny Kortchmar, an aspiring teenage guitarist from Larchmont, New York. The two began listening to and playing blues and folk music together, and Kortchmar quickly realized that Taylor's singing had a "natural sense of phrasing, every syllable beautifully in time. I knew James had that thing." Taylor wrote his first song on guitar at age 14, and continued to learn the instrument effortlessly. By the summer of 1963, he and Kortchmar were playing coffeehouses around the Vineyard, billed as "Jamie & Kootch".
Taylor faltered during his junior year at Milton, not feeling at ease in the high-pressured college prep environment despite having good scholastic performance. The Milton principal would later say, "James was more sensitive and less goal oriented than most students of his day." He returned home to North Carolina to finish out the semester at Chapel Hill High School. There he joined a band his brother Alex had formed called The Corsayers (later The Fabulous Corsairs), playing electric guitar; in 1964 they cut a single in Raleigh that featured James's song "Cha Cha Blues" on the B-side. Having lost touch with his former school friends in North Carolina, Taylor returned to Milton for his senior year.
There, Taylor started applying to colleges, but soon descended into depression; his grades collapsed, he slept twenty hours a day, and he felt part of a "life that I [was] unable to lead." In late 1965 he committed himself to the renowned McLean Hospital in Belmont, Massachusetts, where he was treated with Thorazine and where the organized days began to give him a sense of time and structure. As the Vietnam War built up, Taylor received a psychological rejection from Selective Service System when he appeared before them with two white-suited McLean assistants and was uncommunicative. Taylor earned a high school diploma in 1966 from the hospital's associated Arlington School. He would later view his nine-month stay at McLean as "a lifesaver ... like a pardon or like a reprieve," and both his brother Livingston and sister Kate would later be patients and students there as well. As for his mental health struggles, Taylor would think of them as innate, and say: "It's an inseparable part of my personality that I have these feelings."
1966–1969: Early career
Taylor checked himself out of McLean and, at Kortchmar's urging, moved to New York City to form a band. They recruited Joel O'Brien, formerly of Kortchmar's old band The King Bees, to play drums, and childhood Taylor friend Zachary Wiesner (son of noted academic Jerome Wiesner) to play bass, and – after Taylor rejected the notion of naming the group after him – called themselves The Flying Machine. 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". In some other songs, Taylor romanticized his life, although he was plagued by self-doubt. 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.
Taylor associated with a motley collection of people and began using heroin, to Kortchmar's dismay, and wrote the "Paint It, Black"-influenced "Rainy Day Man" to depict his drug experience. In a hasty recording session in late 1966, the group cut a single, Taylor's "Brighten Your Night with My Day" backed with his "Night Owl". Released on Jay Gee Records, a subsidiary of Jubilee Records, it received some radio airplay in the Northeast, but only charted to #102 nationally. The same session had recorded other songs, but Jubilee declined to go forward with an album. 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. (A UK band with the same name emerged in 1969 with the hit song "Smile a Little Smile for Me". The New York 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." 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." He hung out in Washington Square Park, playing guitar to ward off depression and then passing out, letting runaways and criminals stay at his apartment. 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. 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.
Taylor decided to try being a solo act and a change of scenery, and funded by a small family inheritance, moved to London in late 1967, living variously in Notting Hill, Belgravia, and Chelsea. He recorded some demos in Soho and, based on Kortchmar's connection of The King Bees having once opened for Peter and Gordon, brought them to Peter Asher, who was A&R head for The Beatles' newly-formed label Apple Records. Asher showed the demos to Paul McCartney, who later said, "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." Taylor became the first non-British act signed to Apple. Living chaotically in various places with various women, Taylor wrote additional material, including "Carolina in My Mind", and rehearsed with a new backing band. Taylor recorded the album from July to October 1968 at Trident Studios, at the same time The Beatles were recording The White Album. McCartney and an uncredited George Harrison guested on "Carolina in My Mind", whose lyric holy host of others standing around me made reference to the Beatles, while the title phrase of Taylor's "Something in the Way She Moves" provided the starting point for Harrison's classic "Something". McCartney and Asher brought in arranger Richard Hewson to add orchestrations to several of the songs and unusual "link" passages in between them; these would receive a mixed reception at best.
During the recording sessions, Taylor fell back into his drug habit, using heroin and methedrine. He underwent visepdone 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. Meanwhile, Apple released his debut album, James Taylor, in December 1968 in the UK and February 1969 in the U.S. Critical reaction was generally good, including a very positive Jon Landau review in Rolling Stone which said "this album is the coolest breath of fresh air I've inhaled in a good long while. It knocks me out." The record's commercial potential suffered from Taylor's inability to promote it due to his hospitalization and it sold poorly; "Carolina in My Mind" was released as a single, but failed to chart in the UK and only made #118 in the U.S.
Apple Corps itself had fallen into chaos, with anarchic business planning and freeloaders taking advantage of it in every direction. In early 1969, to clean up the situation, three of the Beatles brought in Allen Klein, who began purging Apple personnel. Asher did not like Klein; he resigned of his own accord and offered to manage Taylor, to which Taylor agreed. Klein wanted to hit Taylor with a $5 million lawsuit for leaving, but McCartney (a Klein antagonist) and then the other Beatles, overruled him on the grounds that artists should not be holding each other to contracts.
In July 1969 Taylor had a six-night stand at 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. Shortly thereafter, he broke both hands and both feet in a motorcycle accident on Martha's Vineyard and was forced to stop playing for several months. But while recovering, he continued to write songs and in October 1969, signed a new deal with Warner Bros. Records.
Once recovered, Taylor moved to California, keeping Asher as his manager and record producer. In December 1969, he held the recording sessions for his second album there. Entitled Sweet Baby James, and with the participation of Carole King, the album was released in February 1970 and was Taylor's critical and popular triumph, buoyed by the single "Fire and Rain," a song about Taylor's experience in psychiatric institutions and the suicide of his friend, Suzanne Schnerr. Both the album and the single reached #3 in the Billboard charts, with Sweet Baby James selling more than 3 million copies in the United States alone. This success piqued tremendous interest in Taylor - prompting a 1971 Time Magazine cover story - and the single, "Carolina in My Mind," put him back into the charts. Sweet Baby James was received at its time as a folk-rock masterpiece, an album that effectively showcased Taylor's talents to the mainstream public, marked the direction he would take in following years, and made Taylor one of the main forces of the nascent movement. It earned several Grammy Award nominations including one for Album of the Year, and would be listed at #103 on Rolling Stone's 500 Greatest Albums of All Time in 2003. ("Fire and Rain" was also listed #227 on Rolling Stone's list of the Greatest Songs of All Time).
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. In October 1970, he performed with Joni Mitchell, Phil Ochs, and the Canadian band Chilliwack at a Vancouver benefit concert that funded Greenpeace's protests of 1971 nuclear weapons tests by the U.S. Atomic Energy Commission at Amchitka, Alaska. (This performance was released in 2009 on the album Amchitka, The 1970 Concert That Launched Greenpeace.) In January 1971, sessions for Taylor's next album, Mud Slide Slim and the Blue Horizon, began. Released in April, the album also gained massive critical acclaim and contained Taylor's biggest Pop single in the U.S., a version of the Carole King standard "You've Got a Friend" (featuring backing vocals by Joni Mitchell, which reached #1 on the Billboard Hot 100 in late July. The album itself reached #2 in the album charts, which would be Taylor's highest position ever on this list). In early 1972, Taylor received his first Grammy Award, for (Best Pop Vocal Performance, Male) for "You've Got a Friend" (King also won Song of the Year for the same song on that ceremony). The album went on to sell 2 1/2 million copies in the United States alone.
November 1972 saw the release of Taylor's following album, One Man Dog. A concept album primarily recorded on his home recording studio, it featured cameos by Linda Ronstadt and consisted of eighteen short pieces of music put together. It was received with generally lukewarm reviews and, despite making the Top 10 of the Billboard Album Charts, overall sales were disappointing. The lead single "Don't Let Me Be Lonely Tonight" peaked at #18 on the Hot 100, and the follow-up, "One Man Parade", barely reached the Top 75. Almost simultaneously, Taylor married fellow singer-songwriter Carly Simon on November 3, in a small ceremony at her Murray Hill, Manhattan apartment. A post-concert party following a Taylor performance at Radio City Music Hall turned into a large-scale wedding party, and the Simon-Taylor marriage would find much public attention over the following years. They had two children, Sarah Maria "Sally" Taylor, born January 7, 1974, and Benjamin Simon "Ben" Taylor, born January 22, 1977.
1974–1976: Career ups and downs
Taylor spent most of 1973 enjoying his new life as a married man, and he didn't return to the recording studio until January 1974, when sessions for his fifth album began. Walking Man was released in June and featured appearances of Paul and Linda McCartney and guitarist David Spinozza. The album was a critical and commercial disaster, being his first album to miss the Top 5 since his contract with Warner. It received poor reviews and sold a mere 300,000 copies in the United States. The title track was a huge disappointment, and failed to even appear on the Top 100 – nevertheless, it stands today as an often reprised fan favorite in concerts.
However, James Taylor's artistic fortunes spiked again 1975 when the Gold album Gorilla reached #6 and provided one of his biggest hit singles, a cover version of Marvin Gaye's "How Sweet It Is (To Be Loved by You)," which featured wife Carly in backing vocals and reached #5 in America and #1 in Canada. On the Billboard's Adult Contemporary chart, the track also reached the top, and the follow-up single, the feel-good "Mexico" also reached the Top 5 of that list. A critically very-well received album, Gorilla showcased Taylor's electric, lighter side that was evident on Walking Man. However, it was arguably a more consistent and fresher sounding Taylor with classics such as "Wandering" and "Angry Blues." It also featured a song about his daughter Sally, "Sarah Maria".
Gorilla was followed in 1976 by In the Pocket, Taylor's last studio album to be released under Warner Bros. Records. The album found him with many colleagues and friends, including Art Garfunkel, David Crosby, Bonnie Raitt and Stevie Wonder (who co-wrote a song with Taylor and contributed a harmonica solo). A very melodic album, it was highlighted with the single "Shower the People", an enduring classic that hit #1 Adult Contemporary and almost hit the Top 20 of the Pop Charts. But the album was not very well-received, reaching only #16 and being highly criticized, particularly by Rolling Stone. Nevertheless 1976 was a huge boom year in the recording business - the year of inception of the "Platinum" disc - and In The Pocket was certified Gold.
Finished his contract with Warner, in November the label released Greatest Hits, the album that comprised most of his best work between 1970 and 1976 and it became with time his best-selling album ever. It was certified eleven times platinum in the US, earning a Diamond certification by the RIAA and eventually selling close to twenty million copies worldwide. It still stands as the best-selling folk album by any artist.
1977–1981: Move to Columbia and maintained success
In 1977 Taylor signed with Columbia Records. Between March and April, he quickly recorded his first album for the label. JT, released that June, gave Taylor his best reviews since Sweet Baby James, earning a Grammy nomination for Album of the Year in 1978. Rolling Stone was particularly favorable to the album – "JT is the least stiff and by far the most various album Taylor has done. That's not meant to criticize Taylor's earlier efforts [...]. But it's nice to hear him sounding so healthy." JT reached #4 in the Billboard charts, selling more than 3 million copies in the United States alone. The album's Triple Platinum status ties it with Sweet Baby James as Taylor's all-time biggest selling studio album. It was propelled by the highly successful cover of Jimmy Jones and Otis Blackwell's "Handy Man", which hit #1 on Billboard's Adult Contemporary chart and reached #4 on the Hot 100, earning Taylor another Grammy Award for Best Male Pop Vocal Performance for his cover version. The song also topped the Canadian charts. The success of the album propelled the release of two further singles – the rocking "Your Smiling Face" (an enduring live favourite) reached the American Top 20 and "Honey Don't Leave L.A." didn't enjoy much success, barely reaching the Top 75.
Back in the forefront of popular music, Taylor collaborated with Paul Simon and Art Garfunkel in the recording of a cover of Sam Cooke's "Wonderful World", which reached the Top 20 in the U.S. and topped the AC charts in early 1978. After briefly working on Broadway, he took a one-year break, reappearing in the summer of 1979 with the cover-studded Platinum album Flag, featuring a Top 30 version of Gerry Goffin and Carole King's "Up on the Roof." Taylor also appeared on the No Nukes concert in Madison Square Garden, where he made a memorable live performance of "Mockingbird" with his wife Carly. The concert appeared on both the No Nukes album and film.
In March 1981, James Taylor released the album Dad Loves His Work, whose themes concerned his relationship with his father, the course his ancestors had taken, and the effect he and Simon had had on each other. The album was another Platinum success, reaching #10 and providing Taylor's final real hit single in a duet with J. D. Souther, "Her Town Too", which reached #5 Adult Contemporary and #11 on the Hot 100 in Billboard. The album's title was, in part, drawn from the reasons for Taylor's divorce from Carly Simon. She gave him an ultimatum: cut back on his music and touring, and spend more time with her and their children, or the marriage was through. The album's title was Taylor's answer, and Simon asked for divorce. (The emotional repercussions of the divorce likely served as at least part of the inspiration for "Her Town Too".)
1981–1996: Troubled times and new beginnings
Simon announced her separation from Taylor in September 1981 – saying "Our needs are different; it seem[s] impossible to stay together" – and their divorce became final in 1983. Taylor was living on West End Avenue in Manhattan and on a methadone maintenance program. Over the course of four months starting in September 1983, spurred on in part by the deaths of his friends John Belushi and Dennis Wilson and in part by the desire to be a better father to his children, he dropped methadone and finally kicked his drug habit for good.
Taylor had thoughts of retiring by the time he played the massive Rock in Rio festival in Rio de Janeiro in January 1985. He was encouraged by the nascent democracy in Brazil at the time, buoyed by the positive reception he got from the large crowd and other musicians, and musically energized by the sounds and nature of Brazilian music. "I had... sort of bottomed-out in a drug habit, my marriage with Carly had dissolved, and I had basically been depressed and lost for a while, " he recalled in 1995. "I sort of hit a low spot. I was asked to go down to Rio de Janeiro to play in this festival down there. We put the band together and went down and it was just an amazing response. I played to 300,000 people. They not only knew my music, they knew things about it and were interested in aspects of it that to that point had only interested me. To have that kind of validation right about then was really what I needed. It helped get me back on track." The song "Only a Dream in Rio" was written in tribute to that night, with lines like I was there that very day and my heart came back alive. The October 1985 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.
On December 14, 1985, Taylor married actress Kathryn Walker at the Cathedral of St. John the Divine in New York. Taylor's next albums were partially successful – in 1988, he released Never Die Young, highlighted with the charting title track, and in 1991, the platinum New Moon Shine provided Taylor some popular songs with the melancholic "Copperline" and the upbeat "(I've Got to) Stop Thinkin' About That", both hit singles in the AC radio. During the late eighties, 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, 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 the Lord in Randy Newman's Faust.
1997–2003: Successful comeback
After six years since his last studio album, Taylor released Hourglass, an introspective album that gave him the best critical reviews in almost twenty years. The album had much of its focus on Taylor's troubled past and family. "Jump Up Behind Me" paid tribute to his father's rescue of him after The Flying Machine days, and the long drive from New York City back to his home in Chapel Hill. "Enough To Be On Your Way" was inspired by the alcoholism-related death of his brother Alex earlier in the decade. The themes were also inspired by Taylor and Walker's divorce, which took place in 1996. Rolling Stones found that "one of the themes of this record is disbelief", while Taylor told the magazine that it was "spirituals for agnostics." Critics embraced the dark themes on the album, and Hourglass was a huge commercial success, reaching #9 on the Billboard 200 (Taylor's first Top 10 album in sixteen years) and also provided a big adult contemporary hit on "Little More Time With You". The album also gave Taylor his first Grammy since JT, when he was honored with Best Pop Album in 1998.
On February 18, 2001 at the Emmanuel Episcopal Church, Boston, Taylor wed for the third time, marrying Caroline ("Kim") Smedvig, the director of public relations and marketing for the Boston Symphony Orchestra. They had begun dating in 1995, when they met as he appeared with John Williams and the Boston Pops Orchestra. Part of their relationship was worked into the album October Road, on the song "On the 4th of July." The couple reside in the town of Washington, Massachusetts with their twin boys, Rufus and Henry, born in April 2001 to a surrogate mother via in vitro fertilization.
Flanked by two greatest hit releases, Taylor's Platinum-certified October Road appeared in 2002 to a receptive audience. It featured a number of quiet instrumental accompaniments and passages. Overall, it found Taylor in a more peaceful frame of mind; rather than facing a crisis now, Taylor said in an interview that "I thought I'd passed the midpoint of my life when I was 17." 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.
Taylor performed "The Star-Spangled Banner" at Game 2 of the World Series in Boston on October 24, 2004. In December, he 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. Later on, 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. They performed his song, "Shower the People", with a surprise appearance by Arnold McCuller, who has sung backing vocals on Taylor's live tours for many years.
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. In 2006, 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 1, 2007, 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 released on CD and DVD in November 2007 on Starbucks' Hear Music Label, where he joined with Paul McCartney and Joni Mitchell. The introspective album grew out of a three-year tour of the United States and Europe—featuring some of Taylor's most beloved songs and anecdotes about their creative origins—accompanied solely by the "one man band" of his longtime pianist/keyboardist, Larry Goldings. The digital discrete 5.1 surround sound mix of One Man Band won a TEC Award for best surround sound recording in 2008.
November 28–30, 2007, 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. 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. This album forays into country and soul while being the latest proof that Taylor is a more versatile singer than his best known hits might suggest. The Covers sessions stretched to include "Oh What a Beautiful Morning," from the musical Oklahoma - a song that his grandmother had caught him singing over and over at the top of his lungs when he was seven years old. Meanwhile, in summer 2008, Taylor and this band toured 34 North American cities with a tour entitled James Taylor and His Band of Legends. A additional album, called Other Covers, came out in April 2009, containing songs that were recorded during the same sessions as the original Covers but had not been put out to the full public yet.
During October 19–21, 2008, Taylor performed a series of free concerts in five North Carolina cities in support of Barack Obama's presidential bid. On Sunday, January 18, 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.
Taylor performed on the final The Tonight Show with Jay Leno on May 29, 2009, distinguishing himself further as the final musician to appear in Leno's original 17-year run.
On September 8, 2009 Taylor made an appearance at the twenty-fourth season premiere block party of the Oprah Winfrey Show on Chicago's Michigan Avenue.
On January 1, 2010, Taylor sang the American national anthem at the NHL Winter Classic at Fenway Park, while Daniel Powter sang the Canadian national anthem.
On March 7, 2010, Taylor sang a cover of the Beatles' In My Life in tribute to deceased artists at the 82nd Academy Awards.
In March 2010 he commenced the Troubadour Reunion Tour with Carole King and members of his original band playing shows in Australia, New Zealand, Japan and North America.