Best James Taylor Songs: 10 Confessional Singer-Songwriter Classics

9: Country Road (from ‘Sweet Baby James’, 1970)

“I’m all in pieces,” Taylor sings on Country Road, a song written in the wake of the mental-health problems for which he checked himself into to a hospital in Belmont, Massachusetts, to be treated for severe depression. The hospital had a striking wooded road running by its side, inspiring the song’s title. Though the inspiration for Country Road’s lyrics came out of turmoil, the song, a breathtakingly original one from his debut Warner Bros album, 1970’s Sweet Baby James, expresses the freedom of being alone. Showing off Taylor’s sweet finger-picking guitar style, Country Road featured Randy Meisner, later of Eagles, on bass and was recorded at Sunset Sound studios in Los Angeles.

8: Walking Man (from ‘Walking Man’, 1974)

When Taylor’s father, Isaac, came back from a spell in the US Navy, he developed an alcohol addiction and, in Taylor’s words, “self-medicated”. The singer-songwriter, who faced his own drug problems, wrote the song Walking Man about his father, and it appeared as the opening track on his 1974 album of the same name. In 2015, Taylor candidly told Rolling Stone magazine, “It’s probably typical, but I have a sense that he was emotionally sort of frozen. Walking Man is informed by my longing for him. Dad disappeared for a few years when I was seven, eight and nine. He was drafted into the Navy, and then he volunteered to go to the South Pole. We missed him a lot.” Topping off one of the best James Taylor songs of the era, the strings on the track were arranged by Gene Orloff, a violinist who played with the legendary jazz saxophonist Charlie Parker.

7: Don’t Let Me Be Lonely Tonight (from ‘One Man Dog’, 1972)

Taylor is a master at writing deceptively emotional songs, and one of the best James Taylor songs of this type is Don’t Let Me Be Lonely Tonight, from his 1972 album, One Man Dog. The jazzy romantic ballad reached No.14 on the Billboard charts. One of its distinctive qualities is the skilful saxophone playing by jazz great Michael Brecker. Taylor’s composition has been covered by Johnny Mathis, Liza Minnelli, Joe Cocker and Eric Clapton.

6: How Sweet It Is (To Be Loved By You) (from ‘Gorilla’, 1975)

Lamont Dozier, who died in August 2022 at the age of 81, was one of the Motown songwriters who composed the Marvin Gaye hit How Sweet It Is (To Be Loved By You). In 2005, Dozier was asked about the best versions of his songs and replied: “One of my favourites is James Taylor’s version of How Sweet It Is. He’s made that song his own. I love how he did that song. It’s a different mood than how the song was originally produced.” Taylor released his version as the lead single from his 1975 album, Gorilla, a record on which greats such as Randy Newman and Little Feat’s Lowell George made guest appearances.

5: Mexico (from ‘Gorilla’, 1975)

One of Taylor’s most buoyant songs is Mexico, also released on his Gorilla album, and one he continued to record and play in live performances for the next four decades. The lyrics describe the dream of enjoying a wild night in a Mexican border town. The gorgeous harmony vocals are courtesy of Graham Nash and David Crosby.

4: You’ve Got A Friend (from ‘Mud Slide Slim And The Blue Horizon’, 1971)

James Taylor saw Carole King perform her heart-warming new song You’ve Got A Friend at the Troubadour nightclub in West Hollywood in 1970. He asked King if he could record a version for his third album, Mud Slide Slim And The Blue Horizon, later recalling: “As soon as I heard it, I thought, This is a great, great song. Carole was generous enough to allow me to have the first shot at it.” The song became a No.1 hit in the US and went on to win Grammy Awards for both Taylor (Best Male Pop Vocal Performance) and King (Song Of The Year). The pair performed it together many times, including recording a live version at the Troubadour. King described Taylor’s delivery and arrangement on the original as “perfect”.

3: Sweet Baby James (from ‘Sweet Baby James’, 1970)

Released in February 1970, Sweet Baby James received a Grammy nomination for Album Of The Year. The album’s title track, composed for his new-born nephew James – who was named after the singer – was written after Taylor’s return from England, and done in the style of a cowboy lullaby like the ones penned by Gene Autry or Roy Rogers. As well as dealing with the specifics of family love, the song also reflects on cosmic matters (“Maybe you can believe it if it helps you to sleep”). Easily one of the best James Taylor songs, Sweet Baby James is a gorgeous, well-constructed track with a complicated rhyming scheme (“saddle”/“cattle”), of which Taylor remarked: “The slick internal rhymes hook it together to make it connected. The song is a puzzle that fits together and I am very proud of it.”

2: Fire And Rain (from ‘Sweet Baby James’, 1970)

Fire And Rain, a single from Sweet Baby James, was started in London, sparked by the news that Taylor’s childhood friend Suzanne Schnerr had taken her own life. The haunting song, which also reflects on Taylor’s problems with drug addiction and his sudden fame, featured Carole King on piano. “It seemed like a matter-of-fact song, but it was heavy… the song is very personal, confrontational and candid,” said Taylor. “It’s really a kind of blues, in that it is getting out something hard.” After completing the lyrics, Taylor played the chorus for drummer Joel O’Brien, who told him, “You’ve just written your hit. That’s the song.” The finished recording, produced by regular collaborator Peter Asher, remains one of the great singles of the 20th century.

1: Carolina In My Mind (from ‘Greatest Hits’, 1976)

The first recorded version of Carolina In My Mind, cut while Taylor was recording his self-titled debut album, for The Beatles’ Apple Records, featured Paul McCartney on bass and an uncredited George Harrison on backing vocals. Taylor’s audience always greeted the song so enthusiastically that he went back into the studio in 1976 and cut the definitive version for his Warner Bros-released Greatest Hits album, slowing down the tempo and drawing on the skill of West Coast session musicians such as Dan Dugmore on pedal steel guitar to create a wonderful folk-rock sound.

As a songwriter, Taylor has always been connected to the landscape. He wrote this iconic song on the Spanish island of Ibiza, where he and a Swedish friend called Karen were stranded with no money after missing the last ferry back to Formentera. They sat at an outdoor café all night, where Taylor became nostalgic for his childhood home in North Carolina. “I started getting homesick and I thought of this song and my home so far away and wrote Carolina In My Mind as the sun was coming up,” he recalled of the tune that tops our list of the best James Taylor songs. “Because my audience responds well to it, and because it wears well, I play it almost every time I perform, and I haven’t tired of it.”

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