James Taylor has written hundreds of songs over his incredible career, but only a handful truly stand out as his personal best. During a February 2026 appearance on The Late Show with Stephen Colbert, Taylor came prepared with a carefully chosen list of his top picks.
Narrowing down a lifetime of music is never easy, but these five songs reveal what matters most to him as a songwriter. Get ready to discover the stories and famous fans behind each one.
1. Mean Old Man (2002)
Sometimes it takes a Beatle to confirm your best work. James Taylor chose “Mean Old Man” partly because Paul McCartney personally told him he loved the song so much that he went out and bought the entire album “October Road” just because of it.
That kind of praise from a music legend is hard to ignore. The song appeared on Taylor’s 2002 album and showcases his storytelling at its most grounded and real.
McCartney’s endorsement clearly stuck with Taylor.
2. Millworker (1979)
“Millworker” carries the kind of emotional weight that makes even rock legends take notice. Bruce Springsteen, the king of working-class anthems, has publicly praised this song and even performed it himself, which says everything about its power.
Originally written for a musical based on Studs Terkel’s celebrated book “Working,” the song gives voice to everyday laborers in a deeply moving way. Taylor’s ability to channel real human struggle into melody is on full display here.
Few songs capture that feeling so honestly.
3. Sweet Baby James (1970)
Ask James Taylor which song he has written with the most lyrical craft, and “Sweet Baby James” wins every time. In a 2020 interview, he called it the best song he has ever written, pointing to its complex rhyming scheme and the surprising depth hidden inside its gentle, lullaby-like melody.
Released as the title track of his second album, this song turned Taylor into a household name almost overnight. Decades later, audiences still sing along word for word.
4. The Frozen Man (1991)
Bob Dylan telling you he liked your song after a shared concert is the kind of moment a musician never forgets. “The Frozen Man” earned exactly that reaction, with Dylan personally expressing his admiration to Taylor backstage.
The song tells the eerie, captivating story of a man discovered frozen in ice after centuries. Its cinematic quality and vivid imagery set it apart from anything else in Taylor’s catalog.
Dylan’s approval makes perfect sense once you hear those lyrics unfold.
5. Carolina in My Mind (1968)
Some songs just never get old, and James Taylor feels that way about “Carolina in My Mind” more than any other. He shared in 2020 that he genuinely enjoys performing this song most because his audiences light up every single time, and he has never once grown tired of singing it.
Taylor’s classic debut single launched his entire career back in 1968. The warmth and longing woven through every chord make it feel timeless.
It remains his most beloved crowd-pleaser to this day.
6. Fire and Rain (1970)
Few songs carry the weight of a life-altering moment the way “Fire and Rain” does. James Taylor wrote it while recovering at a psychiatric facility, processing real grief after losing a close friend named Susie.
The song became one of rock’s most haunting confessions, blending personal pain with an unforgettable melody.
Taylor has said this song almost didn’t get written at all, which makes its impact even more remarkable. When a song born from that much raw sorrow reaches millions of people, something almost magical has happened.
It remains one of the most personal pieces Taylor has ever shared with the world.
7. You’ve Got a Friend (1971)
Carole King wrote “You’ve Got a Friend,” but James Taylor made the world fall in love with it. His version won the Grammy Award for Best Pop Vocal Performance in 1972, and Taylor has counted it among his proudest recordings ever since.
There is something about the way he delivers those reassuring lyrics that feels like a warm hand reaching through the speakers. King herself has said Taylor sang it better than she ever could, which is remarkable praise from the songwriter.
That kind of song, one that feels like a promise, stays with listeners for a lifetime.
8. Shower the People (1976)
James Taylor has always believed that love, when openly expressed, changes everything around it. “Shower the People” captures that belief perfectly – it’s a simple instruction wrapped in gorgeous melody.
Taylor wrote it as a reminder that holding back affection only creates distance, and that telling people you love them is never something to be ashamed of. He has performed it thousands of times over five decades and says it never loses its meaning for him.
The song’s message is so straightforward yet so easy to forget in daily life, which may be exactly why Taylor keeps returning to it.
9. Mexico (1975)
Not every great song needs to be heavy. “Mexico” proves that joy, relaxation, and a little wanderlust can carry just as much emotional weight as heartbreak ever could. Taylor wrote it after a trip to Mexico with friends, wanting to bottle that exact feeling of leaving your worries behind somewhere south of the border.
He has described it as one of the most purely fun songs he ever made, which is refreshing coming from an artist often tied to more serious themes. Sometimes the best thing a song can do is make you want to pack a bag and head somewhere warm.
10. Copperline (1991)
Going home in your mind can be just as powerful as going home in real life. “Copperline” took James Taylor back to his childhood in Chapel Hill, North Carolina, painting a vivid picture of creek beds, summer mornings, and the kind of innocence that only exists in memory.
He has said that writing this song felt like excavating buried treasure from his own past. The imagery is so specific and tender that even listeners who never visited North Carolina feel like they grew up there too.
That ability to make something deeply personal feel universally familiar is one of Taylor’s greatest gifts.