Photo: By Paul Keleher [CC BY 2.0 (http://creativecommons.org/licenses/by/2.0)], via Wikimedia Commons
Describing his music is a bit delicate. With a few exceptions in all categories, it’s too calm 
Taylor writes songs that are painfully earnest, that go right for the emotional core. Sometimes, there are drums, sometimes there are horns, but always, always, always there is an acoustic guitar. He relies on continual finger picking rather than a progression of chords, and the notes flow like a river, erratic at times, but always in the same direction.
His albums — 17 of them since 1968 — are always an ebb and flow of ballads and more upbeat tunes. He knows how to tell stories with music, how to transition from verse to chorus to verse, and how to write a guitar bridge like no one else. His songs have earned him a handful of Grammy awards and worldwide recognition.
With a career like Taylor’s, it’s hard to pick just ten best songs; it feels like you’re leaving out more than you’re including. He’s covered quite a few songs, too, but in the interest of including 100% JT songs, those aren’t even on this list. It hurts to leave some of them out, too, like his popular rendition of Carole King’s “You’ve Got a Friend,” or his gorgeous reworking of the Buddy Holly classic “Everyday,” which is transformed thanks to the addition of one extra little bar on the chorus. Still, here is an honest attempt at the ten best James Taylor songs.
# 10 – Mexico
Right from the melodic guitar intro, you know you’re in for a great song. Off Taylor’s 1975 album Gorilla, “Mexico” is a dreamy wish of a story about hanging out south of the border. We know it didn’t happen, as Taylor tells us himself that he’s “never really been, so I don’t really know.” The pop hook is one that you can’t help but sing along with, and those backing vocals? They’re by none other than David Crosby and Graham Nash. By the song’s end, Taylor wants to head to Mexico, and frankly, so do we.
# 9 – Her Town Too
This track from 1981’s Dad Loves His Work album, “Her Town Too” is technically a duet between Taylor and singer songwriter JD Souther. And while Souther’s style is admittedly similar to Taylor’s, this track has JT’s handprints all over it. The sad lyrics about the aftermath of a destroyed relationship, the somewhat positive outlook at the end, and the eminently hummable chorus all smack of Taylor’s style. And, even though “Her Town Too” is a relative downer, it still made the Billboard Top 40. Bonus tip: if you want to get the full ‘80s-ness of this one, you can hunt down a clip on YouTube of the cocaine-fueled Solid Gold Dancers writhing to it.
# 8 – Terra Nova
Back in the 1970s, Taylor was famously married to fellow singer songwriter Carly Simon, and Simon made appearances on several of Taylor’s songs. They’re all lovely collaborations, but perhaps the loveliest is this one about needing to move on with life but feeling the pull of home from his 1977 JT album. It starts off slowly, with a prayer of sorts, then barrels into Taylor declaring that he needs to be “on my way right now,” then shifts back to a slower, wistful bridge before ending in a fantastic ending with Simon echoing Taylor’s lines. It sometimes feels like three song fragments mashed into one, but the final piece is complex enough to be infinitely interesting and melodic enough to keep you singing it over and over.
# 7 – Only One
It’s often been said that repetition is a key component of successful music, and repetition is what makes “Only One” work so well. James Taylor and his backup vocalists (an unlikely but nonetheless amazing all star duo of Don Henley and Joni Mitchell) say the line “You are my only one” well over a dozen times in the span of about four minutes, plus the lines of the verses seem to echo themselves to reveal multiple meanings. It’s a love song that walks the line between desperate and sincere, but it’s held together by a gem of a melody and more than enough percussion breaks and rhythmic variation to keep it interesting.
# 6 – Shed a Little Light
“Shed a Little Light” from JT’s 1991 New Moon Shine
# 5 – Fire and Rain
If you were to ask 100 people on the street to name a James Taylor song, it’s a safe bet that 99 of them will answer, without delay, “Fire and Rain.” His 1970 hit resonated with so many people because of its themes of loneliness, depression, and missing a friend that you know you’ll never see again. (James Taylor wrote the song after learning of a dear friend’s suicide.) The guitar line is as recognizable as the lyrics, and James Taylor’s heartfelt delivery of the lyrics and melody cement this track as one of the defining songs of 1970’s soft rock radio.
# 4 – Copperline
More than 20 years into his spectacular career, James Taylor proved to the world that he wasn’t even close to being done. He released New Moon Shine and his stunning first single “Copperline,” silencing the doubters by the end of the first verse. The hook is as good as any he’s ever written, and the lyrics deliver nostalgia in waves; by the end of the song, we’re all wistful for a childhood that only Taylor had. Universal details abound — the living paycheck to paycheck, the nervous romance of a first kiss, the details of mom’s kitchen and the mystery of dad’s Saturday nights — but Taylor describes a past that we want to remember because it’s set so well to a melody that resolves itself so completely.
# 3 – Carolina in My Mind
Thomas Wolfe insisted that you can’t go home again, and while James Taylor seems to agree, there’s a caveat: you can get lost in your memories of home. It’s not the same thing, exactly, but it’s a nice consolation. Taylor’s 1969 single “Carolina in My Mind” shows us his homesickness and actually makes us thankful for it. Like many of his other songs, the melody is simple, but it’s one that you want to sing along with over and over. And, even though you’re singing Taylor’s words about him missing his home, it strikes a chord with anyone who has ever missed anything and is at least comforted by its memory.
# 2 – Secret O’ Life
It was never released as a single, and it’s almost dirge-like in its tempo, but Taylor’s 1977 track “Secret O’ Life” has been a fan favorite since it was released because of its universal message and perfectly neutral blend of optimism and morbidity. Basically, it’s that we’re all heading toward death, and we have a choice: we can complain about it, or we can “enjoy the ride.” It’s one of those simple truths that we just need to hear every once in awhile — “The secret of life is enjoying the passage of time” — and it is best head in Taylor’s soothing voice over a slowed down 4/4 beat with a beautiful guitar riff.
# 1 – Sweet Baby James
Equally suited for quiet soul searching as it is for putting newborns to sleep (it was, after all, intended as a lullaby for his nephew), his 1970 single “Sweet Baby James” is flawless. It’s hard to point to a single strong point in the song, as he really fires on all cylinders on this one. The melody is catchy, but it doesn’t wear out its welcome. The lyrics are introspective and hopeful, but they’re also playful; the cowboy is just “waiting for summer, his pastures to change,” but he’s also “thinking about women and glasses of beer.”
The guitars lay a good foundation but never get in the way of Taylor’s vocals, which sound as strong as any he’s ever recorded. The song clocks in at a standard single length of just under three minutes, but it never feels long enough. It’s often the tune that garners the strongest reaction from fans when he performs live; if you’ve ever seen Taylor play one of his famous 4th of July concerts at Tanglewood in Western Massachusetts, you know that when he sings about “the turnpike from Stockbridge to Boston,” the crowd cheers so loudly that the show literally stops for a minute. Taylor considers it his finest song, and while that’s reason enough for it to top our list, it’s in the number one spot because of its own merit.
Updated Nov 10, 2020
Walkin Man would definitely be #1 on my list.
Carolina In My Mind
Caroline, I see You
She Thinks I Still Care
River
In the Bleak Midwinter
Suzanne
Fir and Rain
Sweet Baby James
September Grass
Im with you on In the Bleak Midwinter. The song kind of gets lost with the other Christmas songs on the CD but as always with covers that he does, he finds a way to, IMO, make them his own.
JT didn’t Write “September grass” (his friend John Sheldon did), but it’s a truly great song.
Great JT list:: You have the wrong Album cover for”Copperline”. Should be New Moon Shine!!!!!! Have to find a spot for ” Close Your Eyes”. Fool to Care”””!!!
Totally agree with Close your eyes?
A classic concert finale, if he doesn’t do “Sweet baby James”
I eat breathe and sleep I eat breathe and sleep James Taylor James Taylor
“You can close your eyes” and “Wanderin’ “
Very good list! I’d have Bartender’s Blues around #9 because James and Linda Ronstadt were perfect together
Shower the People…favorite of all time
Amy. Just a perfectly wonderful article of The Master of Man and Guitar, Mr James Taylor! No one comes close to they way he does it and you picked a perfect 10!!
1. Sweet Baby James
2. Fire and Rain
3. Carolina On My Mind
* The people that did the rankings are, how shall I say, way off.
I Will Follow
Only a Dream in Rio
Copperline
I Was a Fool to Care
Hymn
Captain Jim’s Drunken Dream
Blossom
Carolina in my Mind
Walk Down That Lonely Road
Never Die Young
What about “Shower the People”? That’s a favorite in my house.
Walking Man = #1
Caroline I see you.
October Road.
September Grass
Don’t let me be lonely tonight
Mexico
Fire and Rain
Walkin Man.
Whenever your ready
Mean old man
Something in the way she moves
How could you forget “There’s something in the way she moves” from his very first double album on Apple? Some of those cuts were remixed and put on the American release of “Sweet Baby James.”
“Shower the People” is a personal anthem for me. It’s always my favorite part of his live shows and brings bittersweet tears for those who’ve passed on and those I can still physically embrace.
I’ve always loved “My Love is Like A Red, Red Rose” and ” Smilin’ Face”. Definitely my favorites.
Not in any order:
• You Can Close Your Eyes
• Daddy’s Baby
• Nothing Like A Hundred Miles
• Shower The People
• Bartender’s Blues
• Traveling Song
• The “One Man Dog” Mash up that starts with “Hymn” and ends with “Jig”
• Song For You Far Away
• Native Son
• lighthouse
• New Hymn
• Wandering
• Something In The Way She Moves
• Carolina In My Mind
If I went to a JT concert where he played these gems with full 4 part harmony arrangements from the albums, I could easily say that would be the best concert I EVER saw and heard!!
Everyone’s JT top ten is going to be different….!
“I Was a Fool to Care”
“Shed a Little Light”
“Don’t Let Me be Lonely Tonight”
“Mexico”
“October Road”
“How Sweet it is to be Loved by You”
“Sweet Baby James”
“Country Road”
“Handy Man”
“Shower the People”
Walking Man is my #1 lifetime favorite. Really great music and lyrics. I’ve seen him play it in concert 10 times.
JT Top 10 is an almost impossible job. While many of the best-selling classics surely were written in the early years, I’d like to throw in a word for songs written in the latter part of his career. There is hardly any other artist in his generation of singer-songwriters that has managed to consistently release gem-after-gem, just as brilliant as “Sweet baby James” or “Carolina in my mind”, always fresh, and with ever increasing attention to subtle arrangements and top notch sound. Plus consistently one of the very best bands and backing vocalists is the business. Go ahead and count great songs on his latest trio of full-length studio albums with JT originals (“Hourglass”, “October Road” and his 2015 “Before this world”) and you’ll find just as many truly wonderful songs as on any other trio of JT albums in the 70s. You betcha.
So folks, here’s a bunch of “younger” greats:
Snowtime
Angels of Fenway
4th of July
Caroline I see you
My traveling star
Another day
Boatman (OK, written by brother Livingston)
New hymn
Baby boom baby
Letter in the mail (sadly overlooked)
Yes! Baby Boom Baby featuring the late genius of Michael Brecker R.I.P (prominently in the coda).
Knockin’ ‘Round the Zoo
Traffic Jam
Steamroller
Mexico
Mockingbird
Shower the People
Mexico
Handy Man
Machine Gun Kelly
Walkin Man
He has so many great songs it is hard to whittle them down. But no Country Road, Shower the People,, Something in the Way She Moves, or You Can Close Your Eyes?
If I May…
1 Sweet Baby James
2 Fire and Rain
3 Carolina
4 Something…
5 Country Road
6 You Can Close Your Eyes
7 Shower the People
8 Mexico
9 Steamroller
10 Walking Manu
Just my opinion….
My number one : you can close your eyes
second: mill worker
third: fire and rain
We listen to JT radio station on Pandora. Our patients love the music and feeling. It soothes them while they undergo therapy. I have customized it with thumbs up/thumbs down to make it a very pleasant sound. Kinda wanta be in North Carolina while I listen to it. “Her town too” is one of my favorites. Too many gems; not enough time!
I always related to “The Frozen Man” but, sadly after he and Yo Yo Ma turned one of the best most joyful songs known to mankind, into a dirge “Here Comes the Sun”.. I kinda turned away from JT’s mournful music. I didn’t even buy his last album.. which is unheard of.. for God’s sake, like a million others I bought a guitar because of JT.
I have been to countless concerts and purchased many guitar books..
His guitar playing is top notch.
Everyone seems to forget ” you’ve got a friend”. Saw my 17th JT concert last month. The annual pilgrimage seems to keep me connected.
We saved that one for our Top 10 James Taylor Duets article.
Sweet Baby James
Something in the Way
Brighten Your Night With my Day
You Can Close Your Eyes
Her Town Too
Shed a Little Light
Copperline
Follow
Anywhere Like Heaven
Rainy Day Man
EVERYONE ABOVE is right! ALL songs are absolutely the best ones.
But, uh, I can’t imagine this list without “You Can Close Your Eyes” and “Shower The People”.
Shower the People is amazing and I always smile when I listen to Steamroller
“Shower the People” is a forever favorite and I always smile when I hear “Steamroller”
I love…..Long Ago and Far AwaY
Doesn’t seem to appear on anyone’s list?????
..