When James Taylor appeared on The Late Show with Stephen Colbert, Colbert asked him a deceptively simple question: “What are James Taylor’s top five James Taylor songs?”
For a six-time Grammy Award winner with a career spanning more than five decades, the answer turned into a thoughtful look back – guided in part by praise from some of music’s biggest legends.
“Paul McCartney got in touch with me at one point,” Taylor, 77, told Colbert on the Feb. 5 episode. “He commented on a song that I had written, said he really liked it, that he bought the album because of it. So that’s got to go in there…that’s called ‘Mean Old Man.’”
Next on the list was “Millworker,” from the 1979 album Working. Written for the musical adaptation of Studs Terkel’s book, the song tells the story of a woman laboring long hours in a steel mill. Taylor revealed that Bruce Springsteen admired the song and even performed it once himself, a testament to its emotional power and storytelling strength.
No list would be complete, however, without “Sweet Baby James.” Released in 1970 on the album of the same name, the gentle lullaby became one of Taylor’s signature songs and helped define the singer-songwriter movement of the era. The album’s success launched Taylor into mainstream stardom and paved the way for the Grammy wins that followed throughout his career.
Another deeply personal selection was “God Have Mercy on the Frozen Man,” from 1991’s New Moon Shine. Taylor told Colbert that Bob Dylan once praised the song after the two performed together at a benefit at Harlem’s Apollo Theater.
Rounding out the list was “Carolina in My Mind.” First released in 1968 on Taylor’s self-titled debut album, the song has endured as one of his most beloved works, later re-recorded for Greatest Hits.
More than half a century later, the song remains a fitting closer – both to the list and to a conversation reflecting on his remarkable musical legacy.