The Tragic Real-Life Story Of James Taylor

After the psychedelic revolution of the '60s but before the California rock and disco of the mid-'70s became the soundtrack of their lives, with-it adults got down to the sounds of a generation of sensitive, sweet-voiced singer-songwriters. This group of guitar-clutching or piano bench-planted musicians included such melodic poets as Carole King, Cat Stevens, Carly Simon, and Jim Croce, but none set the tone and endured for as long or as much as James Taylor. 

The man affectionately known by fans as "J.T." and "Sweet Baby James" has created such emotional and soothing jams like "Fire and Rain," "You've Got a Friend," and "Mexico." Offstage and off the wax, however, Taylor's life has been far from smooth — fraught with tragedy, personal problems, and potentially fatal health issues. So let's take a look to long ago and far away and watch the one-man parade that is the tumultuous and tragic life of James Taylor.

James Taylor had major health issues as a young adult

James Taylor hit big in the 1970s, but his artistic journey began in the previous decade. Unfortunately, Taylor's young adulthood was stymied by urgent health issues, both mental and physical. At age 16, Taylor dropped out of high school in order to form a band with his brother, Alex Taylor. The future star was living in New York at the time, and in 1965, the 17-year-old developed a deep and persistent depression. Taylor later told the Chicago Tribune that he "spent [his] college education money staying at a psychiatric hospital." That facility was the McLean Psychiatric Hospital, and that's where Taylor took the time to start writing songs in earnest, often looking inward for material and thus using music for its therapeutic purposes.

After starting a band called the Flying Machine in 1966, Taylor decamped to England, where he won the favor of Peter Asher, a talent scout who worked for the Beatles' Apple Records. That label released Taylor's first, self-titled album in 1968. It didn't sell very well, and Taylor couldn't immediately promote it because he returned to the United States to seek professional help for drug addiction. Taylor's life and career were on track by the early 1970s, only for him to suffer another setback. He was riding his motorcycle near his home on Martha's Vineyard in Massachusetts when he crashed and sustained serious injuries, breaking both of his hands, which makes playing a guitar or holding a songwriting pen rather difficult.

The sad stories behind 'Fire and Rain'

According to Snopes, there's a widely accepted theory as to the meaning behind James Taylor's 1970 hit "Fire and Rain." Evidently, some friends arranged for Taylor's girlfriend to fly in and surprise him at one of his concerts, but the plane crashed on the way. That's hinted at in the lines that go "Suzanne, the plans they made put an end to you," as well as "sweet dreams and flying machines in pieces on the ground." 

However, the truth about "Fire and Rain" is more complicated and arguably even more tragic. Suzanne is a real person — Suzanne Schnerr, a friend from Taylor's teen days with whom he played in a band called the Flying Machine. "We used to hang out together, and we used to get high together," Taylor said in Timothy White's James Taylor: Long Ago and Far Away. In 1968, when he was recording his first album, he learned that Schnerr had committed suicide months earlier, the news purposely withheld by their mutual friends because "they didn't want to shake me up." (Fyi, the "they" in the line "the plans they made" refers to "'ye gods,' or basically 'the Fates,'" Taylor said.) 

As for the rest of the song, according to a 1972 interview with Rolling Stone (via The Girl in the Song), the second verse is about his personal and professional anxiety, while the third verse "refers to [his] recuperation in Austin Riggs," a residential treatment facility.

He was addicted to heroin

One of James Taylor's first professional music projects was a late-'60s, New York-based band called the Flying Machine. Not only was that the place where Taylor honed the musical chops that would propel his career for decades, but it's also where he got his first taste of hard drugs. 

According to Oprah's Master Class, the drummer in that band, Joel O'Brien, introduced him to heroin. Thus began an addiction to opiates that lasted for the better part of 20 years. From late 1967 to early 1968, "I was clean," Taylor told Rolling Stone. "Then I started to take a lot of codeine. I went to Europe and started to take opium, and then I got into smack heavily for about nine months." After five months in an American rehab facility, he quit that "smack," a slang term for heroin. Upon his discharge, a Chicago doctor got him onto a sobriety-aiming "methadone maintenance" regimen, but after about 18 months of that, in the summer of 1971, Taylor was back on drugs.

James Taylor was addicted to methadone

While James Taylor successfully kicked his heroin addiction in the early 1970s, he soon became reliant on methadone, a sometimes addictive opiate that's used to help heroin users wean themselves off that harder drug. "My really serious addiction was to methadone," he told Billboard. Taylor used it from the mid-1970s up until 1983, when he decided he needed to free himself of all intense substances. The 1982 overdose-related death of his friend John Belushi is what inspired his big life change. 

In retrospect, Taylor believes that drugs took their toll on him, particularly socially and emotionally. "One thing that addiction does is, it freezes you," Taylor told The Telegraph. "You don't develop, you don't learn the skills by trial and error of having experiences and learning from them and finding out what it is you want and how to go about getting it, by relating with other people. You short-circuit all of that stuff and just go for the button that says this feels good over and over again." In 1983, he began the journey to sobriety, utilizing 12-step programs as well as vigorous exercise. "Eventually, that sort of just scours the devil out of you," Taylor told Oprah's Master Class, "so that's the best practical advice I can give — sweat it out."

He had a troubled marriage to Carly Simon

James Taylor has been married three times. His second marriage, to actress Kathryn Walker, lasted about a decade, and he's currently hitched to Boston Symphony Orchestra trustee and publicist Caroline "Kim" Hessberg-Taylor. Taylor's first marriage, however, is his most famous and tumultuous. In November 1972, he married fellow iconic Baby Boomer troubadour Carly Simon. Together, they recorded the hit novelty duet "Mockingbird" and had two children together, but otherwise, the marriage was full of drama and bad news. 

In her memoir Boys in the Trees (via The Washington Post), Simon wrote extensively of Taylor's drug use, emotional distance, and infidelity, including the day in 1976 when he told her "he had to get checked out for the clap," i.e. gonorrhea. The marriage ultimately ended in 1983, after Simon tired of Taylor's two-timing. At one point, Simon wrote (via Showbiz 411) that Taylor set up his mistress in a studio apartment a few blocks from the family home in New York.

Taylor has reportedly remained cold toward his ex-wife. When Simon wanted to perform at a charity event after the 2013 Boston Marathon bombings, she "was told that she couldn't, and the reason was that [Taylor] was going to be there," Simon revealed to Salon. In 2018, Taylor told The Telegraph that he doesn't speak with Simon anymore, quipping, "That's sort of the point about divorce."

James Taylor virtually witnessed John Lennon's murder

December 8, 1980 is one of the saddest and darkest days in music history. That's when Mark David Chapman approached the legendary John Lennon outside of his home, New York City's Dakota building, and shot the former Beatle several times, ending his life at the age of 40. The shocking murder hit Taylor hard, as he and Lennon knew each other. Taylor had been the first act signed to the Beatles' Apple Records, and in the late '60s, as Taylor told The Guardian, he "gave John opiates," which he believes led to a heroin problem for Lennon, which in turn accelerated the Beatles' eventual split

Fast forward a decade to 1980, and Taylor and Lennon were virtually neighbors, as Taylor lived in the building next door to the Dakota. And on the day before Lennon's death, Taylor had a frightening encounter with Chapman. As Taylor told the BBC, he was at a subway stop when he met the future assassin. "The guy had sort of pinned me to the wall and was glistening with maniacal sweat and talking some freak speak about what he was going to do and his stuff with how John was interested, and he was going to get in touch with John Lennon." The next day, Taylor says, "I heard him shot — five, just as quick as you could pull the trigger, about five explosions."

His older brother died on James' birthday

Certain skills can run through a family's genetic code, and that seems to have happened to the Taylor family. James Taylor is obviously a famous musician of some renown, but his younger siblings, Kate Taylor and Livingston Taylor, have both released plenty of work. The older Taylor brother, Alex, was also a singer-songwriter, releasing half a dozen albums through the '70s and '80s, until his career and life were cut short with his death in 1993 in his late 40s. 

Like James and their father, whom Taylor says struggled with alcoholism, Alex Taylor similarly suffered with substance abuse. "Great song interpreter, great singer," Livingston Taylor said of Alex to Living Legends Music, but "his discipline that might have taken him to playing instruments was destroyed by his continual drinking and that really interrupted his musical development." In March 1993, Alex Taylor traveled to the Orlando area to hit the studio where he'd recorded his blues-rock albums Dancing with the Devil and Family and Friends. While there, Alex passed out and was declared comatose by the time he arrived at a local hospital. He never regained consciousness and died six days later, on March 12, 1993 — James Taylor's 45th birthday. The death has been attributed to the musician's long battle with alcoholism.

He endured multiple tragic deaths in a very short period

Emotionally-driven singer-songwriters like James Taylor pull from deep within their psyches and souls to create the kinds of songs that resonate with millions of fans. For example, in 1997, he released his fourteenth studio album overall but just his second of the decade, the platinum-certified Hourglass — which The New York Times called "possibly his best ever." That might have to do with the raw emotional place Taylor was in when he put the record together. 

Hourglass came on the heels of an onslaught of personal tragedies for Taylor. His brother, Alex, died young in 1993. Then his father, University of North Carolina School of Medicine dean Issac Taylor, passed away in 1996. Not too long after the death of Taylor's father, his stepmother died, too, and then so did his best friend, Don Grolnick, a session musician who helped shape the sound of Taylor and numerous other '70s singer-songwriters. Plus, Grolnick was the guy who led Taylor's band. As if that wasn't enough, Taylor's ten-years-long marriage to Kathryn Walker fell apart in the same chunk of time.

James Taylor had to pay for a relative's financial crimes

James Taylor's extended family suffered a major tragedy in late 2019. Granted, nobody died, but then tragedy can just as easily involve money, disappointment, and crime. Albert Hessberg III is the brother of Taylor's third wife, Caroline "Kim" Hessberg-Taylor. He's also Taylor's Alcoholics Anonymous sponsor, having helped the singer stay on the clean and sober track for years. According to the Times Union, Hessberg worked as a trusts and estates lawyer in New York state up until May 2019, when he entered guilty pleas in charges of wire fraud, mail fraud, and firing a false tax return. "Over a decade ago, I made a terrible mistake that spiraled out of control," Hessberg wrote in a U.S. District Court filing, then adding, "I desperately needed money for my family, needing to pay for school tuitions, income taxes, and other necessities." That was his explanation for why he swiped around $2 million from his clients and firm. Later that year, Hessberg was disbarred and then sentenced to more than five years in federal prison.

On behalf of his brother-in-law, Taylor sent a letter of support to the court. "How did such a thoroughly decent man commit such a breach of trust?" Taylor wrote. "We all ask ourselves and each other but, in the end, we are baffled." Ultimately, Taylor stepped in and acted like a good guy, offering to pay $1.7 million in restitution to his brother-in-law's victims.