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, and again on October 25, 2007. In December 2004, 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 and albums 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.
On 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. An 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 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, including Russ Kunkel, Leland Sklar, and Danny Kortchmar. They played shows in Australia, New Zealand, Japan and North America, with the final night being at the Honda Center, in Anaheim, CA. The tour was a major commercial success, and in some locations found Taylor playing arenas instead of his usual theaters or amphitheaters. Ticket sales amounted to over 700,000 and the tour grossed over 59 million dollars. It was one of the most successful tours of the year.
Taylor owns a house in the Berkshire County town of Washington, Massachusetts.
On September 11, 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.
On November 22, 2011, Taylor performed "Fire and Rain" with Taylor Swift at the last concert of her Speak Now World Tour in Madison Square Garden, as well as her own song Fifteen. Then, on July 2, 2012, Swift appeared as Taylor's special guest in a concert at Tanglewood.
He has been active in support of Barack Obama's 2012 reelection campaign, and opened the 2012 Democratic National Convention.
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