James Taylor’s Life in Songs: Family, Love, and Escapism

Can you just picture James Taylor on a chilly afternoon, building a fire in a vast barn, feeding logs of wood into an antique fireplace? Yeah, I can too. But that’s exactly what he does on a frequent basis. In fact, he calls it a “ritual.” Taylor’s barn sits on a compound he owns in western Massachusetts – a space whose ceilings reach over 27 feet that doubles as his private recording studio. It’s the studio in which he cut parts of his past five albums, including American Standard, his latest.

The title is fitting because the album salutes the Great American Songbook with the singer’s signature take on songs from the 1920s through the ’50s. The album was also aptly timed: It was the 50th anniversary of Sweet Baby James, the album that made Taylor a superstar at the age of 21. He became part of the singer-songwriter movement of the early ’70s, and the man is still going strong.

How Old Is James Taylor?

For some reason, one of the most burning questions on the Internet regarding James Taylor is how old the musician is. The answer folks, is that he’s (currently) 72 – he was born on March 12, 1948. Knowing the fact that it’s been five whole decades since Sweet Baby James, you would think he would say something like ”Those 50 years just flew by.”

But that’s not what Taylor feels at all. When asked by Parade if it feels like half-a-century has passed since hit songs like Fire and Rain, he responded with an enthusiastic “Yes!” He added that he feels the “full weight of those 50 years” which involved touring, raising children, and his relationships with his current and former wives. “I feel it all.”

A “Taylor-Made” Album

The artist “Taylored” the American standards on his new album to his particular liking. Instead of the grand, orchestral classics like Moon River and The Nearness of You, he focused on his voice and guitar work. The songs he chose for the album were the very standards that sparked his own creative life. “I was emulating these songs when I was first trying to write,” he explained.

In Taylor’s youth, he spent hours just immersing himself into the music he heard in the house he grew up in, which was in Chapel Hill, North Carolina (although he was born in Boston). Today, he says he longs for that “dreamy time,” before cell phones and social media.

He Went Unnoticed by His Parents

According to Taylor, it was in that kind of space that you could construct “coherent and larger thoughts,” adding that “distraction is a modern curse.” While those years may have been “dreamy,” he also experienced his share of significant trauma.

Taylor’s father was the dean of medicine at the University of North Carolina, but he also abused alcohol. Eventually, it killed his marriage to Taylor’s mother, which unfortunately blinded both parents to their son’s growing mental issues during his teens. As Taylor recalls, “They didn’t have time to notice what was happening with me.” For Taylor, his teen years were years of turmoil.

Joined a Band, but Felt Out of Touch

The turmoil that Taylor experienced in his teens forced him to leave the boarding school he was in and enter a mental institution. When Taylor was at the Milton Academy boarding school in Boston, he had already started faltering during his junior year, feeling hit by the high-pressure college prep environment.

He returned home to North Carolina, and it was there that he joined a band that his brother Alex formed called The Corsayers (they later became The Fabulous Corsairs). Taylor played electric guitar, and in 1964, they cut a single in that featured his song Cha Cha Blues on the B-side. But Taylor was out of touch with his school friends in North Carolina, and he went back to Milton Academy for his senior year.

A Nine-Month Stint at a Psychiatric Hospital

During his second round at Milton, when he started applying to colleges, he felt that he was living a “life that [he was] unable to lead,” and he grew depressed. He was sleeping 20 hours each day, and his grades floundered. In 1965, he committed himself to a psychiatric hospital in Belmont, Massachusetts.

There, he was treated with antipsychotic drugs, like chlorpromazine, and the organized days gave him a sense of time and structure. At the time, the Vietnam War was escalating, and Taylor appeared before the Selective Service System with two white-suited McLean assistants.

It Was a “Lifesaver”

He was uncommunicative, and thus received a psychological rejection from them. Taylor ended up earning his high school diploma in 1966 (from the hospital’s associated Arlington School). Later, Taylor came to see his nine-month stay at McLean as “a lifesaver.”

Both his brother Livingston and sister Kate became patients and students of their own at the hospital, as well. Once Taylor was released, he started developing his already promising musical talent. He was only a child when he started taking cello lessons. By 1960, he was learning to play the guitar.

A “Crazy and Dangerous” Period

And while his guitar playing evolved, so did his affinity for drugs, leading up to what would become two decades of addiction. “It was crazy and dangerous,” he said of that period. “I’m really lucky to have survived it.” Taylor’s use of drugs was his way of self-medicating; he was “trying to get normal,” is the way he put it.

He also noted that he had been diagnosed and treated for depression his whole life. He describes himself as being “mildly depressed,” even to this day. But the plus side is that he’s been sober for the past 35 years – nearly more than half of his life. And the thing that keeps him sober? Exercise. “It was the only way I could stand to be in my own skin.”

James and Carly: The Golden Couple

The way he sees it, his addiction ruined his earlier relationships, including his marriage to singer Carly Simon. Taylor and Simon were defining voices of the ‘70s, each topping the charts with their individual work as well as their duets.

But the “golden couple” lasted only a decade. The singer-songwriters married in 1972 and welcomed two children. By 1983, they were divorced. Their beginning is worth noting, though. In early 1971, Simon was walking down the street with her sister and passed a newsstand holding a copy of TIME magazine that had a cartoon Taylor on the cover.

Summers in Martha’s Vineyard

According to Simon, without thinking, she blurted out, “I’m going to marry him.” She said he was perfect for her in every way. The pair came together after several fleeting encounters. They had known each other in their youth since both their families spent the summers on Martha’s Vineyard.

Taylor remembers seeing Simon and her sister Lucy performing in Martha’s Vineyard in the mid-’60s, and found her “quite attractive.” You should know that at the time, he was 14 and she was 18. They met again in 1971 when Simon opened for Cat Stevens at The Troubadour in L.A.

An Offer He Couldn’t Refuse

At that time, Taylor was dating Joni Mitchell. Meanwhile, Simon would frequently think of Taylor and listen to his album Sweet Baby James every day. Later that year, Simon saw him play at New York’s Carnegie Hall, and she went up to him during the intermission, giving him an offer he couldn’t resist.

“If ever you want a home-cooked meal while you’re here in New York, I’d love to make lunch with you,” she told him. His reply: “What about tonight?” After that night’s show and after-party, the two returned to her apartment and ate some Sara Lee banana cake. It was “perfect for our first meal together,” she recalled.

An Unceremonious Proposal

It was Simon who suggested they get married, and Taylor was hesitant… at first. That afternoon, he told her he had thought about it and “maybe they should get married.” Taylor was 26 and Simon 30 when they married in a low-key ceremony.

They had their kids, Sally and Ben, who grew up to be singer-songwriters of their own. Taylor and Simon recorded a number of duets together, but outside of the studio. Their relationship was “bipolar” – going from “love to hate, lust to loathing, and back again.” A major challenge was Taylor’s addiction, which was a mainstay throughout their marriage.

Getting a Call From Bianca Jagger

Simon admitted that she didn’t understand the extent to which he was addicted when their relationship began. She recalled witnessing him shooting up in front of her one night. For Taylor, he reasoned it might “take away the cat-and-mouse game” of his addiction.

“I can’t have you and the habit at the same time. I can’t,” is what Taylor reportedly told her. But it wasn’t just the drugs. Their marriage was also tainted by infidelity, on both sides. In fact, Simon claimed Bianca Jagger (Mick’s then-wife) called Taylor…

Affairs of His Own

Bianca told him that Simon had been unfaithful – that she and Mick Jagger were having an affair. Taylor, however, said that he trusted his wife. Taylor reportedly had affairs of his own with “a few other women,” eventually setting up a separate place with one of his dancers while still living with Simon and their kids in New York.

After their eventual divorce, Taylor chose to refuse to speak to Simon, for reasons she claims she doesn’t know. For whatever reason, he has purposely chosen not to speak about her very much in interviews.

Kathryn: The Wife Who “Saved” Him

It’s his second wife, actress Kathryn Walker, whom he credits with helping him get off heroin. They married in 1985, but it ended in 1996. It was before and during his marriage to Walker that Taylor had thoughts of retiring, specifically around the time he played the Rock in Rio festival in Brazil in January 1985.

He said he felt musically energized by both the sounds and nature of Brazilian music. “I had sort of bottomed-out in a drug habit, my marriage with Carly had dissolved, and I had basically been depressed and lost for a while.”

Caroline: His Current Wife

Taylor’s third and current wife is Caroline Smedvig. The two met when she was the head of public relations for the Boston Symphony Orchestra, and they got married in 2001. Together, they have two twin boys, Rufus and Henry. Amazingly, throughout all these trials and tribulations, failed and successful marriages, and everything in between, Taylor’s career has never wavered.

The five-time Grammy winner and Rock and Roll Hall of Famer has earned gold or platinum albums in each of the past five decades. “I’m deeply grateful for where I ended up — for my marriage, my family, my job,” says Taylor, who will always be known as Sweet Baby James.

Taylor has said that many of his songs tell the tale of his life. So let’s look at some of them…

Rainy Day Man (1967)

“It does you no good to pretend, child

You’ve made a hole much too big to mend

And it looks like you lose again, my friend

So go on home and look up your rainy day man”

In 1966, Taylor was living at the Albert Hotel in New York with his best friend, Zach Wiesner. The two of them wrote this song. Taylor described how they had one of only two rooms at the hotel that weren’t destroyed in a previous fire, “so it was pretty cheap.” Taylor explained that the song was a “dope connection,” referring to all the time he spent in drummer Joel “Bishop” O’Brien’s apartment, doing dope (and more) with him.

Something in the Way She Moves (1968)

“And I feel fine anytime she’s around me now

She’s around me now

Almost all the time

And if I’m well you can tell she’s been with me now

She’s been with me now quite a long, long time

And I feel fine”

Taylor remembers speaking to his father on the phone while he was living in New York, and he didn’t like the way his son sounded. “I was strung out, malnourished and kind of beat,” Taylor recalled. The next day, his father showed up with the family station wagon and drove his son back to North Carolina.

There Was “Something” George Harrison Liked About It

Back home, he took some time to recover, and by Christmas 1967, he had talked his parents into buying him a ticket to London. He had a friend who agreed to let him stay there for a few weeks. His plan was to sing in clubs or on the streets, but he ended up reconnecting with Peter Asher, who started working for Apple Records.

Asher got Taylor an audition with Paul McCartney and George Harrison. He played Something in the Way She Moves. Taylor said the song is about a past girlfriend and the calm one feels in the presence of someone who knows them really well. Then, he heard that Harrison used the title for the opening lyrics of Something, and Taylor was thrilled.

Carolina in My Mind (1968)

“There ain’t no doubt in no one’s mind

That love’s the finest thing around

Whisper something soft and kind

Yes and hey babe the sky’s on fire, I’m dyin’

Ain’t I goin’ to Carolina in my mind”

Taylor was cutting his first album at Trident Studios in London, which was near where the Beatles were recording the White Album. He recalled feeling so lucky to be listening to the Beatles playbacks and watching their recording process. Yet, at the same time, he missed his home in North Carolina. “This captured that feeling of being called away to another place.”

Sweet Baby James (1970)

“Goodnight you moonlight ladies

Rockabye sweet baby James

Deep greens and blues are the colors I choose

Won’t you let me go down in my dreams

And rockabye sweet baby James”

When Allen Klein took over Apple Records in 1969, he let everybody on the label, including Taylor, go except for the Beatles. When Taylor came back to the U.S. and found out his brother Alex had had a baby boy, he decided to write a song for him. After all, the boy was named after him. “It starts as a lullaby, then the second half of the song… talks about what music means to me.” Taylor said he thinks it’s his best song.

Steamroller (1970)

“Well, I’m a steamroller, babe

I’m bound to roll all over you

Yes, I’m a steamroller now, baby

I’m bound to roll all over you”

When Taylor returned to London, he came with his heroin habit raging again. There, he went to rehab, which is where he wrote a lot of songs that wound up on the album Sweet Baby James. But Steamroller was from his early band Flying Machine days, “and it was a joke.” As he explained it, “there were a lot of white guys playing the blues… and it seemed comical to me.”

“Well, at Least He’s Still Alive”

Steamroller was meant to be a take-off, as Taylor recalled. Taylor explained that one side effect of being hospitalized – more than once – is that any academic or professional aspirations his family might have had for him were all abandoned.

And so, they basically threw up their hands and said, “Well, at least he’s still alive.” His parents were always supportive of his music, but he felt as though he was “disenfranchised and alienated.” As he saw Sweet Baby James take off, which was immensely gratifying and everything he wanted, success was still a major adjustment for him. Hence, steamroller.

You’ve Got a Friend (1971)

“You just call out my name

And you know wherever I am

I’ll come running, to see you again

Winter, spring, summer or fall

All you have to do is call

And I’ll be there

You’ve got a friend”

Carole King and Taylor were playing at L.A.’s Troubadour together. She had just finished writing You’ve Got a Friend, which she said was a response to the song Fire and Rain (whose chorus goes “I’ve seen lonely times when I could not find a friend”). King’s song-form response was, “Here’s your friend.”

Thanks, Carole King

As soon as Taylor heard it, he wanted to play it. Not long after that, he was in the studio, recording Mud Slide Slim and the Blue Horizon. They had already cut two songs that day, but Taylor recalls them still having studio time as well as energy.

Peter Asher suggested they play King’s new song. They did, “and it sounded great.” The thing is, though, that there was one problem: He never even asked King if it was okay. So, he “sheepishly” called her up and told her, “We didn’t really mean to do it, but we’ve recorded You’ve Got a Friend. Luckily for him, she didn’t mind and told him to go for it.

Walking Man (1974)

“Moving in silent desperation,

Keeping an eye on the Holy Land

A hypothetical destination, say

Who is this walking man?”

Taylor said that he wrote a lot of songs about his father, whom he said “was emotionally sort of frozen.” Walking Man is about Taylor’s longing for his father who disappeared for a few years when Taylor was between the ages of seven and nine.

He had been drafted into the Navy, and then volunteered to go to the South Pole. Taylor and his family missed him a lot. His mother, who had five kids within six years in the countryside of North Carolina, was desperately waiting for her husband to come home. “That always stayed with me, somehow.”

A Junkie’s Lament (1976)

“It’s halfway sick

And it’s halfway stoned

He’d sure like to kick

But it’s too far gone

They wind him down with the methadone

He’s all on his own”

Taylor has numerous recovery songs, but this one is a warning to not think of a junkie as a functioning human being. “Heroin should’ve killed me about five times, but it never did,” he stated.

He admits that his kids suffered from their father being an addict. This song, among his other related songs, can really show what it was like for him to be in that state of mind in his relationships. “All of your relationships suffer, no question about it.”

Secret ‘O Life (1977)

“The secret of life

Is enjoying the passage of time.

Any fool can do it,

There ain’t nothing to it.

Nobody knows how we got

To the top of the hill.

But since we’re on our way down,

We might as well enjoy the ride.”

Taylor wrote this song “in a little patch of sunlight” while he sat on the steps of a house he was “literally building on Martha’s Vineyard.” It took about 10 minutes to write it, as though the lyrics were “just sitting there in the guitar.” He also said the title was supposed to recall Life Savers flavors, like “Pep-O-Mint” or “But-O-Rum.” It was a jab at the arrogance of writing a song titled “The Secret of Life.”

Only a Dream in Rio (1985)

“More than a distant land over a shining sea

More than the steaming green

More than the shining eyes

Well they tell me it’s only a dream in Rio”

Taylor was in another stint in rehab, this time to kick a methadone addiction after some really bad “jackpots,” a term he uses to describe how he humiliated himself and the people who love him by screwing up.

He tried to undergo a detox at a place in Connecticut, but he relapsed and continued to use. It wasn’t until the saxophonist Michael Brecker got him involved with the Twelve Steps that Taylor started to take it seriously.

A Turning Point in His Life

Even after he got clean, he wasn’t sure whether there was life “on the other side” for him. He also didn’t know if he could write anymore. Then he went down to Rio de Janeiro in Brazil to play the Rock in Rio festival. Gilberto Gil, a Brazilian songwriter, left a guitar for Taylor to play.

When he walked onstage and saw that 300,000 people knew his songs, he felt a real rush of energy. It was extremely powerful and felt as though he was “two feet off the ground coming off the stage.” It was a real turning point in his life, which always warrants a song.

Never Die Young (1988)

“We were ring-around-the-rosy children

They were circles around the sun

Never give up, never slow down

Never grow old, never, ever die young”

This song, as Taylor described, was written from the perspective of someone who essentially gave up on life. But the narrator is looking at the lives of two young people who are not caught up in the chaos of life as he knows it (“They were true love written in stone/ They were never alone/ they were never that far apart”). It’s a sad song, he admits, but it’s also a hopeful and celebratory one.

Copperline (1991)

“Half a mile down to Morgan Creek

Leaning heavy on the end of the week

Hercules and a hog-nosed snake

Down on Copperline

We were down on Copperline”

This is another song about his home, dad, and childhood. “I felt like I was part of a landscape in those days,” Taylor said. He and his wife Caroline (also known as Kim) were raising their kids in the countryside, but it was a different country life that he grew up in. He said it was “connected, constantly connected.”

Enough to Be on Your Way (1997)

“So the sun shines on his funeral

Just the same as on a birth,

The way it shines on everything

That happens here on Earth.

It rolls across the western sky

And back into the sea

And spends the day’s last rays upon

This f**ked-up family, so long old pal.”

Taylor’s brother Alex was also an addict and passed away in 1993 because of it. Taylor admitted that there was “a sense of relief when he died,” for both him and his family. Only a year or so later Taylor finally understood the “totality of his life rather than just the shambles of its end, the pain of it.” It was at that point that he wrote this song.

Mean Old Man (2002)

“I was a mean old man,

I was an ornery cuss,

I was a dismal Dan,

I made an awful fuss

Ever since my life began, man.”

Paul McCartney called Taylor up one day and said that when he first heard this song, he assumed it was either Frank Loesser or Cole Porter. Taylor was thrilled. And when Bob Dylan told him that his other song, Frozen Man, was great, that was “enough” for him. “I’ll be fine as long as every once in a while, someone like Paul McCartney or Bob Dylan says, ‘Keep going, kid’.”

Angels of Fenway (2015)

“Grandmama was a Fenway fan

Even after Grandad died

I still remember her holding my hand

Taking me along for the ride

She was born in 1918

Last year that the Red Sox won

Back then when they sold the Babe

Something that they never should’ve ever have done”

The song was finished in May 2014, but Taylor had the music for seven years before that. He knew for a while that he wanted to write about the “miracle 2004 season against the Yankees.” He wrote it as a grandmother who was born during the last time the Red Sox won, and she died on the day they finally did it again.

Keeping Up With the Taylors

Taylor became a dad in 1974, when his first and only daughter, Sarah “Sally” Taylor, was born to him and Carly Simon. Taylor’s first son, Ben, came next. His marriage to Kathryn Walker resulted in no children, despite having been together for over a decade.

Then, in 2001, Taylor married Caroline Smedvig, and the two had twin boys, Rufus and Henry. The family remains a happy one to this day. I guess third time really is a charm. The fam jam lives together in their Lenox, Massachusetts home.

Let’s take a look at each of the Taylor kids, shall we?

Sarah “Sally” Taylor

Sally Taylor is an artist and, like her parents, a singer-songwriter who made a name for herself on her own accord. Early in her career, she joined the indie band The Slip but left the group eventually to go solo.

Born on January 7, 1974, the now 47-year-old, has a degree in medical anthropology from Brown University under her belt. She’s a mom to one, son Bodhi Taylor Bragonier. She’s married Dean Bragonier. She’s also a philanthropist, who focuses on the issues of land mines in Southeast Asia.

Ben Taylor

Born on January 22, 1977, Benjamin Simon Taylor is, like his mom, dad, and sister, a musician. Aside from music, the 44-year-old has also acted. You may have seen him in American Dreams, Always and Everyone, and then he played himself in The Vineyard.

Ben was young – in his early 20 – when he delved into music. It didn’t take long for him to become a beloved artist. The singer took a brief break from music in his later career. He returned to the industry recently, in 2020, regaining his vast audience.

Henry and Rufus Taylor

Taylor’s son, Henry, was born in April 2001. The now 20-year-old hopes to venture into his family’s business like his half-siblings and dad. But he is still just a kid at this point. According to his Instagram bio, he describes himself as a musician and “lover-of-guitar.”

As for Henry’s twin brother, Rufus, he seems to be the only member of the Taylor fam jam with no interest in the arts. Then again, he might just be a late bloomer. By looking at his Instagram page, he has an interest in a different kind of art: the culinary arts.