James Taylor recently shared his personal favorite songs from his extensive catalog during a segment on The Late Show with Stephen Colbert. The legendary singer-songwriter, at 77, was more than willing to delve into his musical history and reveal the songs that hold special meaning for him. When asked to rank his top five, Taylor acknowledged the difficulty of the task but approached it with enthusiasm, jotting down notes and offering thoughtful explanations for each choice. His selections provide insight into the moments and collaborations that have shaped his career, with a few surprises and noteworthy anecdotes along the way.
James Taylor’s Top Pick: “Mean Old Man”
The first song Taylor named is “Mean Old Man,” which appears on his 2002 album, October Road. This track holds particular significance because of its connection to a direct compliment from one of the most influential figures in music history. Taylor recounted that Paul McCartney from The Beatles reached out to him at one point. McCartney expressed his appreciation for the song and mentioned that he bought the entire album after hearing it. Taylor reflected on this encounter, noting, “Paul McCartney got in touch with me at one point. He commented on a song that I had written. He said he’d really liked it, that he bought the album because of it.” This endorsement from McCartney meant a great deal to Taylor, and it secured “Mean Old Man” a prominent spot in his top five.
Recognizing Influences and Collaborations
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“Millworker”
Next on Taylor’s list is “Millworker,” a track that was originally written for the Broadway musical Working. Although it debuted on stage, Taylor later recorded his own version, which was included on his 1979 album, Flag. The song has a special place in his heart because of the admiration it received from Bruce Springsteen. Taylor shared that Springsteen was particularly fond of the song, highlighting the strong connection and respect Taylor has within the songwriting community. The song’s themes resonate with many listeners, capturing the struggles and hopes of working-class Americans, and its origins in musical theater showcase Taylor’s versatility as a composer.
Classic Hits and Iconic Songs
“Sweet Baby James”
One of James Taylor’s most famous tracks, “Sweet Baby James,” naturally found a spot on his list. Featured on his self-titled album Sweet Baby James from 1970, this song has become an emblem of his career and is often considered his signature piece. Its gentle melody and poignant lyrics encapsulate Taylor’s folk-rock style and have cemented it as a timeless classic. Fans worldwide associate the song with comfort and nostalgia, and Taylor himself regards it as one of his essential works that helped define his sound.
“The Frozen Man”
Taylor also highlighted “The Frozen Man,” a song from his 1991 album New Moon Shine. This track is noteworthy not only for its haunting melody but also for the praise it received from fellow songwriting legend Bob Dylan. Taylor recounted an incident where he and Dylan performed together at the Apollo Theater in New York. During that gig, Dylan approached him and said, “I really like that song, ‘God Have Mercy on The Frozen Man.'” The line “Lord have mercy on the frozen man” appears multiple times in the song, which features reflective lyrics and emotional depth. It remains one of Taylor’s deeply personal compositions, appreciated for its storytelling and lyrical richness.
Early Works & Hidden Gems
“Carolina In My Mind”
Rounding out his top five is “Carolina In My Mind,” a song that dates back to Taylor’s early career. Released on his debut self-titled album in the late 1960s, it captures a sense of longing and nostalgia for the American South. The song became an instant favorite among fans and remains a staple in his live performances. Its warm, melodic tune showcases Taylor’s songwriting prowess and his ability to evoke vivid imagery through music.
Fan Reactions and Missing Favorites
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Despite his thoughtful selections, fans on social media couldn’t help but notice the absence of one major hit—”Fire and Rain.” Many expressed surprise or disappointment that the song, arguably one of Taylor’s most emotionally impactful and commercially successful, was not included. Comments flooded platforms like Instagram, with users exclaiming, “Oh come onnnn where is Fire and Rain???” and “that’s a JT classic .” Others joked that “Fire and Rain” should be considered Taylor’s number six hit, given its significance.
However, some fans acknowledged the challenge of narrowing down such an extensive catalog. With decades of music, it’s nearly impossible to pick only five favorites. One admirer wisely pointed out, “There are just way too many songs,” emphasizing how difficult it is to pick the best tracks from Taylor’s rich discography. Others affectionately suggested that “all of them” should be on the list, highlighting the deep love fans have for his entire body of work.
While Taylor’s list didn’t include every fan favorite, it provides a meaningful look into the songs that have personal resonance for him. His selections reveal a mixture of admiration from iconic artists, songs written for musical theater, and timeless classics. It underscores the fact that, for Taylor, certain songs represent milestones, personal memories, or moments of artistic validation.
This story originally appeared on Parade on February 6, 2026, and captures a rare, candid glimpse into the musical mind of one of America’s most enduring singer-songwriters. Fans and newcomers alike can appreciate the depth of Taylor’s eclectic taste and the stories behind some of his most beloved songs, which continue to resonate with audiences decades after they were written.
