Describing his music is a bit delicate. With a few exceptions in all categories, it’s too calm to be rock and roll, too groovin’ to be folk, and too 4/4 to be country. Really, it’s soft rock veering into easy listening territory — a label that might feel like an insult in some cases, but in this case, it’s totally apropos. Can you think of any other songs that are as easy on the ears?
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 was always a strong song, but in recent years, it’s taken on a higher degree of gravitas. It starts with an a capella choral intro of Taylor and singers turning their “thoughts today to Martin Luther King.” You can imagine where it goes from there: a plea to accept that for all of our differences, we’re really the same, and we’re all on this planet together, and we should cut the crap and start treating each other like human beings. James Taylor is obviously much more eloquent in his expression of this, and between the strength of the lyrics and the avalanche of voices, it’s enough to give anyone chills.
# 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.