When brooding folk-rocker James Taylor appeared on The Simpsons, they jokingly referred to him as the “Mild Man of Rock”. Well, when it comes to his personal life, you might wanna grab a glass of milk because it’s burn-your-face-off spicy.
1. His Life Was Anything But Laid Back
On the surface, there’s nothing threatening about James Taylor. At his peak, the sensitive, acoustic guitar-wielding tunesmith was basically a male Taylor Swift—in fact, the superstar songstress’s parents even named her after him.
Like Swift, Taylor was able to turn heartbreak into massive album sales. Unlike Swift, however, his life path veered into darkness, tragedy, and danger way too many times.
Laurel Maryland, USA, CC BY-SA 2.0, Wikimedia Commons
2. He Came From Money
It’s safe to assume that your family isn’t hurting for cash if you were born in the same Boston hospital where your father worked as a doctor. Despite this being the case when little James Taylor entered the world on March 12, 1948, he would soon find out that all the old money in the world couldn’t stop the freight train of heartache that would soon be heading his way.
CMA/Warner Records. Public domain, via Wikimedia Commons
3. He Was Off To An Embarrassing Start
Kids are always exploring and experimenting and seven-year-old Taylor was no different. One afternoon, when he thought he was alone, he dipped into the family record collection and pulled out some…show tunes! He started belting out “Oh, What a Beautiful Mornin'” from Oklahoma! without realizing that his grandmother was in the next room.
Oh, if only this could have been his last encounter with the burning fires of shame instead of the first of many.
Billboard magazine, Wikimedia Commons
4. He Had A Single Mom (Kind Of)
Life wasn’t totally rosy while James was discovering his love of show tunes, however. It was around this time that his father was sent away on a two-year expedition to the South Pole. It’s hard to not have a father figure during those formative years, but shortly after his father’s return, we’re guessing that young Taylor was wishing that his dad had stayed far, far away.
Universal, Two-Lane Blacktop (1971)
5. He Had Big Daddy Issues
A reunion upon dear ol’ dad’s return should have been a joyous time. Sadly, Taylor’s father came home with more than souvenirs—he now had a major drinking problem. James, his siblings, and their mother had to walk on eggshells to avoid the senior Taylor’s terrifying outbursts.
James later said of his father, “There’s a mysterious energy to someone who lives with a tragedy like this”.
Universal, Two-Lane Blacktop (1971)
6. His Family Life Began To Crack
Eventually, the elder Taylor’s drinking problem became too much for James’s mother to handle. Not even all of the idyllic summer getaways at Martha’s Vineyard could stop her from filing for divorce. Even though James was now in his teens, the split sent the whole family spiraling even deeper downward.
Universal, Two-Lane Blacktop (1971)
7. He Took A Break From Life
Taylor’s family turmoil was the catalyst for what Taylor calls his “teenage emotional breakdown”. His mindset became so troubling that at the urging of teachers and friends, he was sent to McLean, a psychiatric hospital outside of Boston. Even though Taylor checked himself in, for the next 10 months he was basically unable to leave.
As the Taylors would soon discover, James wasn’t the only family member in urgent need of mental support…
John Phelan, CC BY 3.0, Wikimedia Commons
8. He Confused His Parents
Getting psychiatric help in the mid-60s wasn’t as normalized as it is today, not even in a privileged family such as Taylor’s. James had started a trend—within his family, at least. Shortly after he checked himself into McLean, his sister Kate and brother Livingston joined him. According to Taylor, his other brother Alex “was already off the rails” by then. But that wasn't all.
Columbia Records, Wikimedia Commons
9. He Found His Muse
If subsequent events of Taylor’s life are any proof, the time spent in the mental hospital didn’t quite “cure” his ailments. His time out did give him lots of time to start writing some songs, though. In fact, in yet another recipe for disaster, he checked out early—against medical advice—because he was so eager to get his music career off the ground. 
Universal, Two-Lane Blacktop (1971)
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10. He Hit The Road
Where does a young aspiring musician with a suitcase full of songs go when he breaks out of the mental institution? The Big Apple, of course. While there, he hooked up Danny Kortchmar, a musician friend he’d met during his family’s summers at Martha’s Vineyard. The pair found Joel O’Brien to play drums and called their new band the Flying Machine.
The band started playing quite regularly around Greenwich Village, but something sinister prevented the Flying Machine from taking off…
Universal, Two-Lane Blacktop (1971)
11. A Monkey Climbed On His Back
The young musicians were full of potential and ready to take on the world. In fact, shortly after Kortchmar met Taylor, he could tell that “James had that thing”. Unfortunately, O’Brien, the band’s drummer also had another thing—a bad habit—and one fateful day, he introduced it to Taylor. Thus began Taylor’s long, long running battle with addiction.
Universal, Two-Lane Blacktop (1971)
12. He Lost The Magic
Introducing hard substances to someone who is mentally unstable and has a family history of addiction is never going to go well. It didn’t help that, according to Taylor, “It was as easy to get high in the Village as get a drink”. After the Flying Machine’s first single tanked, Taylor would try to cope by getting high and playing guitar in Washington Square.
Taylor was careening toward the first of many rock bottoms.
Medill DC, CC BY 2.0, Wikimedia Commons
13. He Sunk Pretty Low
As if following some sort of junkie playbook, Taylor started losing friends. Bandmate Kortchmar was especially dismayed at how Taylor had changed. Taylor started spending time with shady people and would often get high and invite them back to his apartment. With his money gone, his health failing, and most relationships ruined, he quickly ran out of lifelines.
Universal, Two-Lane Blacktop (1971)
14. He Must Have Been Desperate
One dark and hopeless night, Taylor decided it was time for a Hail Mary and made a late-night call to his father. Thankfully, the old man was able to sense the urgency of the situation and flew from North Carolina to New York where he rented a car, filled it full of James’s worldly possessions, and spent all night driving his son home—but he also gave him a terrifying warning.
Paul Keleher, CC BY 2.0, Wikimedia Commons
15. His Father Tried To Scare Him Straight
The all-night drive must have been harrowing for both father and son, but Taylor’s dad did his best to make use of the time. Taylor’s father told James that opiates are the ultimate enemy of the Taylor family. According to James, “As a kid, his uncle said to him: ‘If you’re a Taylor and you touch an opiate, you’re finished. You can kiss your entire life goodbye”. Yikes.
Of course, we know by now that Taylor did not heed his father’s caveat for long.
16. He Tried To Recover
It is interesting to ponder where Taylor would be if his family didn’t have money. Luckily they did and while back in North Carolina, he was able to go to rehab for six months and get surgery to fix his vocal cords because he had damaged them trying to sing in a raspy style.
Once he was feeling better, a family inheritance allowed him to give his music career another try in an entirely new location.
The White House, Wikimedia Commons
17. He Impressed Some Big Names
A change of scenery can do wonders for one’s creativity and in 1967, London was the place to be. Once there, James got his old friend Kortchmar to pull some strings and before he knew it, Taylor was the first non-British act on the Beatles’ brand-new Apple Records. After hearing Taylor, Paul McCartney said, “Wow, he’s great”.
Despite this career coup, it wouldn’t be long before Taylor’s demons reared their ugly heads.
18. He Was On The Brink
By now, Taylor had made it further in his career than many musicians could ever dream of. It was the swingin’ 60s, he was in London recording his first solo album, and he was hanging out with the Beatles. In fact, George Harrison loved Taylor’s “Something in the Way She Moves” so much that he used the title as the opening line for his song “Something”.
Unfortunately, by 1968, Taylor was on the brink of throwing it all away—and bringing another Beatle down with him.
Harry Pot / Anefo, Wikimedia Commons
19. He Said The Quiet Part Out Loud
Everyone went a bit nuts in 2020, but in an interview that year with The Guardian, James Taylor’s candor was jaw-dropping. He spoke of how plentiful opiates were in London in the 60s. OK, we know what’s coming. But then Taylor said, “I was a bad influence to be around the Beatles at that time, too…Because I gave John opiates”.
Cue the record scratch. According to many, John Lennon did pick up a the awful habit in 1968, which means Taylor may have had a hand in breaking up the Beatles.
Library of Congress, Wikimedia Commons
20. He Succumbed To His Vices
After potentially setting events in motion to destroy one of the world’s most successful pop groups as well as himself, Taylor decided it was time for treatment. He bounced from a British rehab to New York and then Stockbridge, Massachusetts. Because of this, he wasn’t able to properly promote his first album.
While it didn’t make the impact he had been hoping for, word of mouth worked wonders.
The White House, Wikimedia Commons
21. He Drew A Crowd
Life was looking up for Taylor, at least for now. It was the summer of 1969 and he was on the newcomers’ stage at the famous Newport Folk Festival. The fact that it was raining and Taylor was the last act, did not deter the passionate crowd. Something else did, though. After only a few songs, Taylor was mysteriously sent offstage.
The White House, Wikimedia Commons
22. He Had A Bad Break
The wet yet ardent fans cheered for a solid five minutes, hoping that Taylor return. Instead, an organizer announced that the concert was over because the Apollo 11 astronauts had just landed on the moon. A disappointed Taylor may have lamented that he only played for 15 minutes, but Rolling Stone called Taylor’s 15 minutes more magnetic than anything else during the festival.
Rena Silverman, CC BY 3.0, Wikimedia Commons
23. He Was Immortalized
Strangely enough, the aborted folk festival gig wouldn’t be Taylor’s only encounter with NASA. After becoming a superstar, he received The Simpsons treatment in the 1994 episode “Deep Space Homer”. Despite a crisis on board, it’s Taylor's job to serenade the floating astronauts.
“Listen, Aldrin,” he says. “I’m not as laid-back as people think…I’m gonna play and you’re gonna float there and like it”.
20th Television Animation, The Simpsons 1994
24. He Experienced A Plot Twist
The truncated folk festival gig was small potatoes compared to what was about to happen to 21-year-old Taylor in the weeks that followed. He’d gotten over his addiction and mental issues (for now) and had even started writing his next album. Just as he was preparing to make his next career moves, however, disaster struck.
Unknown Author, Wikimedia Commons
25. He Crashed And Burned
It’s not surprising that even the most worldly 21-year-old can be prone to making some really bad decisions. While hanging out with friends in Martha’s Vineyard, Taylor decided to take a spin on a swiped motorcycle they found in the woods. As Taylor raced through the forest, he suddenly realized the brakes didn’t work and ended up crashing into the trees. Ouch.
26. He Was Pulverized
A guitarist’s hands are basically his way of making a living and in the accident, Taylor had broken his hands, his right ankle, and left foot. He had casts all over his body and was out of commission for several months. On the plus side, he had lots of time to think about the material for his next album, including one exceptionally dark and haunting song.
Featureflash Photo Agency, Shutterstock
27. He Poured His Heart Out
After the accident, Taylor channeled his pain into his breakout album Sweet Baby James. In another Taylor Swift parallel, the public was very fixated on unlocking the hidden story behind the song “Fire and Rain”. One theory was that it was about Suzanne, a girlfriend of Taylor’s who had perished in a plane crash. Sadly, the truth was even more heart-wrenching.
28. His Friends Kept A Dark Secret
The Suzanne from “Fire and Rain” was an old flame from Taylor’s New York days. The truth behind the song was that after the pair had grown apart, Taylor was distressed to learn Suzanne had ended her life by throwing herself in front of a subway train. What made it all worse was that Taylor’s friends kept the news from him for months as they didn’t want to send him spiraling.
29. He Was An Addict At Heart
Despite his friends’ best efforts, James fell back into the arms of his demons. By the early 70s, he realized that it was time to kick the hard stuff so he went on a treatment program. Like a true addict, though, he became hooked on illicit substances for almost a decade. Sadly, his next wake-up call was not without collateral damage.
30. He Found A New Addiction
Even though Taylor knew that he couldn’t keep up his serious addiction, it wasn’t until his good friend John Belushi overdosed in 1982, that Taylor finally got the message he needed—stop using. He enrolled in a 12-step program and, strangely enough, an extremely vigorous exercise regime.
He even told Oprah, “That’s the best practical advice I can give—sweat it out”.
National Lampoon's Animal House (1978), Universal Pictures
31. He Found His Soul Mate
In the early 70s, Taylor had a lot more on his plate than his addiction issues. In November 1972, just as his fourth album was getting a lukewarm reception, he married singer-songwriter Carly Simon. The marriage experienced soaring highs in the form of duets, collaborations, and two kids, and plummeting lows, many of which ended up in the gossip pages.
Unknown Author, Wikimedia Commons
32. His First Marriage Was A Wild Ride
Of his marriage to Simon, Taylor said, “I was very young…I mean you marry an addict, you just have no idea who this person is, and he doesn’t have any idea who he is either. It’s terrible”. Sadly, Taylor’s addiction and emotional distance weren’t his only flaws. Something even more troubling broke Simon’s heart.
Kathleen Ballard, Wikimedia Commons
33. His Ex Kissed And Told
Being married to Taylor for 11 years was no walk in the park. Luckily for us, much of Carly Simon’s 2015 memoir, Boys in the Trees, trashed Taylor—and the spurned songbird did not hold back on juicy details. She describes how on one jaw-dropping day in 1976, Taylor broke some very disturbing news to his loving wife.
Wikimedia Commons
34. He Did Her Dirty
It’s never a good sign when someone says, “We need to talk,” and presumably the same held true for Carly Simon when Taylor broke the news that “he had to get checked out for the clap," AKA an STI. This was the mother of his two children, the person he had vowed to be faithful to. Sadly, for Simon that wasn’t the only shameful story about her ex.
Arthur D'Amario III, Shutterstock
35. He Liked His Cheating To Be Convenient
Not only was Taylor picking up STIs while fooling around behind Carly Simon’s back, but he also had the nerve to set up a secret love nest for his mistress "Evey" that was just a couple of blocks away from the family apartment. When Simon got wind of the fact that Taylor wasn’t just going to that apartment to “rehearse,” she developed a diabolical plan.
36. His Wife Was, Ahem, Motivated
What do they say about a woman scorned? Watch out! Simon’s first order of business was to have a locksmith secretly copy the keys to the love nest. Then, one day when an oblivious Taylor was looking after the kids, Simon made her move. She used the keys to slip into the apartment and confront the mistress. Chaos ensued.
37. His Wife Was Fearless
Simon’s reasoning for confronting her husband’s girlfriend had nothing to do with stirring up drama. She wanted the woman to know that she was “not a character in a story James was telling her…but a real person”. During the confrontation, Evey revealed the cruel things Taylor had said about Simon to justify the affair.
She then put the final nail in the coffin when she calmly said, “We dig each other. You don’t get him”.
38. He Didn’t Have A Conscious Uncoupling
Carly Simon may not have “got” her husband near the end, but in the divorce from Taylor, she did get the 175-acre property in Massachusetts that Taylor bought with one of his first big paychecks when he was 22. The former couple sometimes trade jabs via the press.
In 2018, Taylor said that he and Simon don’t speak anymore and then sneered, “That’s sort of the point about divorce”. 
Peter Trudelle, Flickr
39. John Lennon Came Back Into His Life
We’ve already established that Taylor was a bad influence on John Lennon in the 60s—but sadly, that was not the only ill-fated connection the two artists shared. In 1980, the pair were almost Manhattan neighbors, and just the day before John Lennon’s last day on earth, Taylor had a scary encounter with the man who would assassinate his friend…
40. He Had A Fateful Encounter
Taylor didn’t know it at the time, but in retrospect, his encounter with Lennon’s assassin is completely spine-chilling. Taylor was waiting at a NYC subway stop when a strange man accosted him and pinned him to the wall. The unhinged man was very sweaty and he started getting right in Taylor’s face and ranting and raving.
New York City PD, Wikimedia Commons
41. He Was Too Close For Comfort
New Yorkers are experts at handling the unhinged—they have mastered the art of deflecting even the most bizarre attacks with a jaded stare. Taylor was about to do this with the sweaty subway man (aka Chapman) until he started mentioning John Lennon. Chapman said that Lennon was interested in his stuff and he was going to get in touch with him.
In a heartbreaking twist, the very next day, Taylor heard the shots as Chapman executed Lennon in front of his apartment.
42. He Didn’t Rebound
Second time’s a charm? After his first marriage to Carly Simon, Taylor waited a couple of years before marrying actress Kathryn Walker in 1985. It was during his—much calmer—marriage to Walker, who was a friend of John Belushi, that Taylor finally quit substances for good. After 11 years, though, the relationship had run its course.
The couple had been very private during the marriage, but after the divorce, Walker decided to speak out in the most interesting way.
43. His Second Ex Had A Poison Pen
According to conventional wisdom, the best thing for a writer to do is “Write what you know”. Apparently, Taylor’s ex-wife Walker took this to heart. A few years after the divorce, she wrote a novel about an unhappily married woman who can’t stand her famous musician husband. Hmm, sound familiar? Some people thought so.
44. His Life Was A Page Turner
Taylor’s ex-wife admitted to the press that the rather unflattering novel was a thinly-disguised tell-all about her time with Taylor and many of the people around them, including Carly Simon. Walker also admitted that she hadn’t sought Taylor’s approval but wasn’t too concerned, saying, “I think it would make James laugh”.
45. It Was All In His Family
Taylor’s mother was an opera singer and his siblings also had recording contracts. After Taylor made it big, Time magazine published an article called “James Taylor: One Man’s Family of Rock”. About it, Taylor said, “Suddenly after having gone through a kind of chemotherapy to get out of my family I was right back at the center of it”.
Unfortunately for Taylor, his family never stopped causing him heartache.
El Humilde Fotero del Pánico , Flickr
46. His Family Was Doomed
Taylor’s brother Alex was the only sibling who didn’t go to the psychiatric hospital and he may have paid dearly for that. Unfortunately, like his father, he struggled with a drinking problem that likely hampered his musical career. It also did something much, much worse.
47. Fate Was Cruel To Him
Orlando, Florida is usually a happy place, but that wasn’t the case for Taylor’s brother Alex in 1993. While there to record an album, the 47-year-old suffered a heart attack. He went into a coma and ended up perishing six days later—on James’s 45th birthday.
Chuck Fadely, Wikimedia Commons
48. He Had Some Very Intense Years
Wherever Taylor went, it seemed that tragedy was never far behind. Shortly after he lost his brother, Alex, he lost his father, his best friend, and his stepmother. To compound the pain, these all occurred right around the time Taylor’s marriage to Kathryn Walker was crumbling. The emotional turmoil would be enough to send even the most stable person over the edge.
Luckily James turned to something other than substances.
Arnie Lee, CC BY 3.0, Wikipedia
49. He Needed Something To Ease The Pain
Most addicts are the first to claim that they can become addicted to almost anything. Strangely enough, Taylor sought shelter from the storm in the arms of physical fitness. He would religiously cycle, row, and hike for three hours a day, saying, “It was the only way I could stand to be in my own skin”.
Evan Osherow, CC BY 2.0, Wikimedia Commons
50. He Had Bad Blood
In yet another parallel to his namesake Taylor Swift, Taylor had the guts to fight his record company for what was rightfully his. In 2012, he filed a multimillion-dollar lawsuit against his former record label, claiming that the company’s shady accounting resulted in him not getting paid accurately.
One number that can’t be disputed, however, is the fact that Taylor sold 100 million albums over a five-decade career.
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