A 1971 Time cover story – and nearly every piece of writing about James Taylor since then – characterized the musician as a troubled soul and the inevitable product of a family of means that expected quite a lot of its kids. To some extent, it was true. James did find inspiration for much of his life’s work in his emotional torment and the many years he spent fighting drug addiction and depression. And he did hail from an affluent, musically talented family that could afford to send its progeny to exclusive prep schools and expensive private mental hospitals. But now James Taylor in his fifties has the benefit of hindsight to moderate any lingering grudges against a press that persistently pigeonholed him – first as a sort of Kurt Cobain of his day, and much later as a sleepy crooner with his most creative years behind him.

To understand grown-up JT you need to delve into his past. By all accounts, JT’s parents gave their kids – Alex, James, Kate, Livingston, and Hugh – a nearly ideal upbringing. James was born in Boston, but soon the family moved outside Chapel Hill, North Carolina and stayed there for much of James’ childhood. Summers were spent among other affluent families at their home on the island of Martha’s Vineyard off the coast of Massachusetts – a place JT would return to throughout his life. Dr. Isaac “Ike” Taylor, who was dean of the University of North Carolina-Chapel Hill Medical School and served as a lieutenant commander in the U.S. Navy, spent much of the marriage away from the family. Gertrude “Trudy” Taylor was a stay-at-home mom who bore the duties of both parents when Ike was in Antarctica with the Navy for two years. Ike and Trudy Taylor finally divorced in 1972, partly due to the strain of Ike’s return from the Navy to a home run by his wife and full of children with whom he’d lost touch.

Music was, unsurprisingly, a part of everyday life for the Taylors while the children were growing up. At his early concerts, James told the story of his first memory of music: a Tuberose Snuff commercial that he’d heard on the radio. “Trudy, the boy’s singing a snuff commercial,” he recalls his dad saying after making the connection with the song James was singing about “Tuberose: The Mild Snuff.” As a modern follow-up, James accompanied the story with his own signature versions of the song first as he remembered it, and then in a second, updated version for the “smooth 70s.”

James brought home a cello from elementary school, later moving on to a mail-order guitar that his older brother Alex painted blue – strings and all. James was undeterred, taking lessons from his brothers and his new friend on the Vineyard, Danny “Kootch” Kortchmar. Kootch was two years older, but he and James struck up a life-long friendship that inspired James to spend time improving his guitar skills.

James joined his big brother Alex’s band, The Fabulous Corsairs, when the family returned to Chapel Hill. They made very little money playing fraternity parties and high school dances, but it was that live experience that gave James the push he needed with the Fender guitar that had replaced its blue predecessor. The next summer he and Kootch entered a local hootenanny contest on the Vineyard and took home first prize. It was also around this time that James wrote his first original song, “Roll, River, Roll.” He never recorded it in the studio, but fans were treated to a performance of it decades later when he sang it by the campfire during the filming of “Colorado River Adventure,” a National Geographic television special that aired in September 1995.

James went back to school at Milton Academy in Massachusetts, but it didn’t last long due to his growing depression. “Probably typical adolescent stuff,” James told British music magazine MOJO. Partly at his family’s insistence and partly out of a desire to escape school, James spent nine months in McLean Hospital, an expensive mental institution where Taylor siblings Kate and Livingston would also spend time. James speaks of the institution almost fondly, having found time to recover some happiness, explore music at his leisure, and even graduate from the hospital’s own high school during his stay. After nine months James had had enough, though, and a friend named Dave Barry helped him “escape” to Boston without waiting for the hospital to officially discharge him. There James got a job in a leather bindery, but soon after he made his way to Manhattan where he’d take some of his first steps toward a music career.

Old friend Danny Kortchmar was in Manhattan looking to start up a new band, having just broken up his old band, The King Bees. James, Kootch, and old friends Zach Wiesner (bass) and Joel O’Brien (drums) got a gig as the house band for the Night Owl Cafe, a popular nightspot in Greenwich Village. The venue was James’ inspiration for “Night Owl,” which became a part of their set along with “Brighten Your Night With My Day,” “Rainy Day Man,” and his most heavily McLean-influenced tune, “Knocking ‘Round the Zoo.” James didn’t like Kootch’s idea to name the band “The James Taylor Group,” so they called themselves “The Flying Machine” instead. The steady gig was a godsend, but when the band recorded a single of “Night Owl” / “Brighten Your Night With My Day” in 1966 they had no luck getting backing for a full album.

Things turned sour soon after. With the band’s failure to get a record deal and the Village’s easy drug scene, James turned to heroin. Unable to extricate himself from his dismal situation and increasing addiction, he finally called his father in desperation. Ike drove all the way to New York to pick him up and take him back home to North Carolina.

Two years later in 1968 James found himself living in the Notting Hill Gate section of London with the idea in his head that he was going to make a record on his own. He bought some cheap recording time in a low-rent studio, laid down some tracks, and tried shopping it to London record companies. As luck would have it, Kootch put him in contact with Peter Asher of Peter and Gordon fame. Asher was helping the Beatles launch a new record label, and he was willing to give young JT a shot. Asher ended up playing JT’s stuff for Paul McCartney and the others before making James the first outside artist signed to the fledgling Apple Records label.

James’ recollections of that period still reflect those of an awestruck fan miraculously rubbing elbows with his heroes. In between recording sessions for legendary Beatles hits like “Hey Jude,” Asher guided JT through the recording of his self-titled debut. “Knocking ‘Round the Zoo,” “Carolina In My Mind” (mistakenly labeled “Carolina On My Mind” for some early singles pressings), and “Night Owl” – the same songs he’d honed with The Flying Machine – were woven together with avant-garde interludes and a “Greensleeves” improvisation. Even Paul McCartney joined in to play bass on some tracks.

The result, “James Taylor,” came out in the U.K. in November 1968 and in the U.S. the following February. It sold a disappointing 30,000 copies in its first year and wasn’t helped by JT’s return to Austen Riggs hospital in Massachusetts for treatment of his heroin addiction. Rather than promote his new album, JT was forced to spend time after its release recovering from the habit he’d picked up back in Greenwich Village.

Then things began to turn around for JT. A major debut at the Troubadour in Los Angeles in July 1969 marked the beginning of what would be a meteoric rise to fame in America. Under Asher’s guidance, JT signed with Warner Brothers and moved himself to California to begin work on his second album. It wasn’t all smooth sailing, though. Sometime that year JT managed to severely injure his hands – reportedly in a motorcycle accident. It forced him to stop playing until he’d healed, but didn’t sideline plans for the new album.

In March 1970, “Sweet Baby James” was released to enormous sales and almost universal acclaim in the U.S. The album hit platinum status by October and garnered five Grammy nominations. Without question, the song that resonated most deeply with its listeners was “Fire And Rain,” a deeply personal, almost painfully melancholy song that set the tone for an album that would change songwriting for many years afterward. Fans hypothesized and argued about its sometimes literal, sometimes metaphorical meaning and seldom got it quite right. They only knew it spoke to them, inspiring many to pick up the guitar – often for the first time – and try to emulate what they’d heard.

The story behind “Fire And Rain” has reached the point of legend now, in spite of JT’s calm assurances that it’s really not all that difficult to understand. Most commonly, stories are told of the girlfriend, Suzanne, who the band had arranged to fly to meet JT as a surprise while on tour. Her plane crashed, the legend goes, and the tragedy of it all inspired JT to speak of “flying machines in pieces.” The truth, of course, is somewhat different.

JT explains that the song is really about three separate times in his life – three hard times when he thought about giving up. Suzanne was either a friend he’d known at Austen Riggs or a friend of drummer Joel O’Brien’s brother. In either case, JT’s band members heard about her suicide, but at the time they decided he was too strung out on drugs to deal with the loss. JT wasn’t told about it until after he’d finished his debut album in London and ended up writing the song while dealing with his grief. Verse two chronicles the Greenwich Village drug scene, and verse three refers to his escape to London and eventual recovery. The often-misunderstood “flying machines in pieces” referred to the breakup of his band, The Flying Machine, though the alternate explanations persist.

The album’s title song inevitably became connected to JT himself, though it’s only partially about him. The original Sweet Baby James was brother Alex’s son James, who was named after his uncle. JT says the song came to him during a long solo drive on the way to see his nephew for the first time. The result was “simply one of the best lullabies ever composed,” according to the 1971 Time story.

Fans may not have known what to think about “Steamroller,” though. Nestled between the lighthearted “Sunny Skies” and the characteristically easygoing “Country Road” was an unmitigated blues tune with lyrics that seemed downright lewd in comparison to the album’s other tunes. The story behind the song goes back to JT’s Flying Machine days at the Night Owl, and he’d invariably launch into the long-winded explanation at his early shows. The story was clearly as well rehearsed as the song, with only the slightest variation in wording at each telling.

Here, in JT’s own words, is the explanation for “Steamroller” as transcribed from the 1970 JT/Joni Mitchell BBC radio show bootleg:

We played this eight-month long gig at a place called the Night Owl Cafe down in Greenwich Village in New York. It used to be a McDougal and Third, but it might have moved since then. I don’t know.

Anyhow, at that time there were a lot of so-called blues groups in New York City, you know? And they were making a lot of noise with electric guitars and amplifiers that their parents had bought them for Christmas and birthdays and stuff. Their idea of soul was volume. They’d just crank it up, you know? And they were singing all these heavy songs like “I’m a Man” or “I’m a Jackhammer” or “I’m a Steamship” … whatever … “I’m the Queen Mary” [laughter] … “I’m a Ton of Bricks.”

And we weren’t to be left out of all this. So I wrote this next song, which is the heaviest blues tune I know, ladies and gentlemen … called “I’m a Steamroller.” [more laughter as JT goes on the play a hilarious solo version of the song]

Fans who hadn’t heard JT’s explanation probably couldn’t tell if he was serious or not, but they loved it regardless. Now, three decades later, the song is a permanent fixture of JT’s perennial live shows and the only live performance on 1976’s enormous-selling “Greatest Hits.”

The album ended with tongue firmly in cheek. “Suite For 20G,” according to JT, was a last-minute composition to fill the last slot on the new album. They needed one more track, so James hastily stitched together some bits and pieces of songs he’d been working on and the band recorded it. The name refers to the fact that on completion of “Sweet Baby James” they’d receive a $20,000 advance from Warner Brothers.

And the money kept coming. The album hit number one on the charts, gained platinum status by October of that year, and remained a bestseller for two solid years. His career solidly on its way, JT hit the road on his first tour and inaugurated what would be a way of life for him for the next three decades. Notable performances from that era included an April 24 performance at Harvard and a live BBC performance with Joni Mitchell. Both shows were bootlegged and the latter is one of the more common unauthorized JT recordings – usually titled either “In Perfect Harmony” or some variation on “You Can Close Your Eyes.”

Early in 1971 the first public release of the abortive Flying Machine album hit the streets in an obvious effort to get a piece of the phenomenal “Sweet Baby James” sales. Undoubtedly it was done without JT’s permission, but the various labels that distributed it and bootlegged it didn’t seem to worry. At least four different vinyl versions were released – a couple of which were nothing but extremely poor quality copies with new cover art. A legal 1996 release on CD by Gadfly Records made the recording widely available for the first time since the ‘70s, but inexplicably included embarrassing over-produced remixes of two tracks in addition to the original unpolished tracks. Later pressings of the CD ditched the remixes and stayed true to the first release.

The Time cover story hit newsstands in March 1971, further solidifying JT’s dominance of what was being called “The New Rock.” March also saw the release of JT’s one and only starring role in a film: Two Lane Blacktop. Cult film director Monte Hellman asked JT to join “Beach Boy” Dennis Wilson, Warren Oates, and Laurie Bird in an avant-garde road movie that seemed heavily influenced by 1969’s Easy Rider. In interviews, JT reveals his bitterness about the experience of performing in a film where he had no creative control. He and the other actors weren’t even given a complete script. Instead, Hellman handed them just the next day’s dialogue, then asked to perform almost as an improvisation. The results generally didn’t impress audiences or critics, though JT’s female fans probably found a little more to like about the film thanks to his extensive screen time and shoulder-length locks.

While Two Lane Blacktop didn’t contain any JT music, the frustrating experience of acting did inspire JT’s “Riding On a Railroad” on his next Warner Brothers album, “Mud Slide Slim And the Blue Horizon” (1971). Another Peter Asher production, the album’s Los Angeles recording sessions spanned almost two months and included big contributions by two of JT’s leading female contemporaries, Joni Mitchell and Carole King. Mitchell sang backup on three of the tracks, but it was King’s “You’ve Got A Friend” that would have the biggest effect on the album and the longest influence on JT’s still-young career.

JT tells the story of how he came to sing the song that would become one of his best-known hits and a certified Gold-selling single. He’d heard King perform it and complimented her on the tune, so she suggested he perform it, too. He did, but now jokes that he might just have reconsidered it if he’d known he’d be singing it every night for the next thirty years. He certainly didn’t have much to complain about, though. The song was the album’s standout hit – a fact made all the more official early the next year when JT was presented with the “Best Pop Vocal Performance, Male” Grammy and King won the “Song of the Year” Grammy for the same song. While King did appear elsewhere on the “Mud Slide Slim” album, she didn’t perform on JT’s recorded version of her song. Live performances were a different matter, though. JT’s supporting tour for the album included King along with Kootch’s band, Jo Mama, and played to sold-out audiences in 27 U.S. cities.

The album didn’t earn its platinum status on the strength of just one track, either. Two Lane Blacktop-inspired “Riding On A Railroad,” and the hauntingly beautiful “You Can Close Your Eyes” both helped to cement JT’s reputation as a songwriter. Fans got more than the simple, upbeat message of “You’ve Got A Friend” and younger album buyers appreciated the album’s melancholy, even bitter songs just as readily. Like “Riding On A Railroad,” “Hey Mister, That’s Me Up On The Jukebox” tells a tale of an artist lost among the machinery of big business that threatens to overshadow his creativity. What’s become a common refrain today – how an artist can still struggle to find happiness amid overwhelming financial success – had rarely been asked publicly until then.

It’s a question JT is still addressing in his music and interviews to this day. 1985’s “That’s Why I’m Here” title track covered similar ground, but with the benefit of hindsight JT paints a picture of a career and a life in which the good overshadowed the bad and the pleasures of creating music for an audience bring him joy over and over again.

Just when it seemed JT’s fame had peaked, though, he began a ten-year romance that was among the most closely followed and publicly reported as any of its day. JT had known Carly Simon and her well-heeled family (of Simon and Schuster publishers fame) since his boyhood days on Martha’s Vineyard. When they married on November 3, 1972 it ignited a firestorm of media attention that would last throughout their ten-year involvement and beyond. In a handful of print interviews given together, JT and Carly revealed what it was like to live as a household of two rock stars with separate careers that sometimes complemented and often competed. When one scored a hit with an album, the other often wilted. Both admitted varying levels of jealously and resentment that sometimes bubbled to the surface in spite of their staunch loyalty to each other.

Almost from the beginning, external pressures and internal demons threatened to pull them apart. His drug habit still not fully behind him, JT struggled to relate to a wife who had managed to avoid drugs all her life. At the same time, his career was showing no signs of slowing – and neither was he. Even after the arrival of their daughter Sarah (Sally) and son Benjamin, JT continued to tour extensively. Carly readily and publicly admitted that it bothered her, though it didn’t keep him from going out year after year.

Meanwhile, JT released an album in 1972 that returned to the kind of experimentation that had characterized his Apple debut album. The album title – originally “One Man Parade” like the first track – was changed for no good reason at the last minute, says James. “One Man Dog” was a moderate critical success, but its patchwork quilt of music styles and instrumental interludes didn’t include many strong radio hits. The one exception, “Don’t Let Me Be Lonely Tonight,” was included on the 1976 “Greatest Hits” album.

The album’s long list of backing voices included Carole King, Linda Ronstadt, Carly, and Taylor siblings Alex, Hugh and Kate. Much of the album took shape in JT’s rustic cabin – and even just outside of it: “Little David” opens with the sound of a roaring chainsaw, which JT claimed he was able to coerce into hitting specific musical notes after a little practice. The recording sessions weren’t without controversy, though. A disclaimer in the liner notes accompanied James’ drug-inspired “Mescalito,” reading “The opinions expressed in this song are not necessarily those of the supporting musicians and background vocalists.”

Having had a couple years to try and reach equilibrium in their personal and artistic partnership, James and Carly’s closely scrutinized marriage hit a fever pitch of publicity on the release of their most successful collaboration. “Mockingbird” was a standout track on Carly’s “Hotcakes” album and was also a certified Gold single on its own. The song became synonymous with the pair, drawing ecstatic audiences to their feet whenever the two performed it live. They didn’t lack for opportunities, either, since James launched a four-week U.S. tour in April 1974 to promote the June release of “Walking Man.”

“Walking Man” was one of JT’s most thematic albums, with tracks like “Migration,” “Fading Away,” and the title track exploring the emotions of autumn and “the coming of winter,” according to JT. The album also saw the return of Paul McCartney as a collaborator for the first time since JT’s debut album. One track, though, may have been too topical. The poignant, politically charged lyrics of “Let It All Fall Down” drew cheers of approval from disillusioned Americans who shared JT’s disgust with President Nixon and the Watergate scandal. But the day after the song’s release as a single (as a B-side for “Daddy’s Baby”) Nixon resigned and the sentiment lost its punch. The single fizzled and did little to help the album’s sales. Touring did help, though, and James set out for a second supporting tour in July with The Manhattan Dirt Riders and Linda Ronstadt.

In late 1974 JT started the process or recording “Gorilla” in Los Angeles. Of the eleven tracks, “Mexico” was the hit that would stick with JT most consistently for the rest of his touring career. JT told Leeza Gibbons in 1992 that “Mexico” came to him while taking a break during the recording of the album. “I went down to spend a long weekend in Mexico with some friends down in Puerto Vallarta and while I was down there, this thing just … sometimes you go some place, you know?” “Gorilla” hit stores in May 1975, with David Crosby and Graham Nash adding harmonies to “Mexico” and “Lighthouse.” JT’s cover of the Holland/Dozier/Holland hit “How Sweet It Is (To Be Loved By You)” got good airplay and later joined “Mexico” on 1976’s “Greatest Hits.”

In May 1974 JT played Carnegie Hall with special guests David Crosby and Carole King. Their performance of “You’ve Got A Friend” was released nearly twenty years later on King’s 1994 release, “The Ode Years.” After tours with a full band in April and July, JT closed 1975 with an eight-city solo tour. Then, a year after the release of “Gorilla,” JT hit the road again in April to support the May release of “In the Pocket.” Its first single, “Shower the People,” included the B-side “I Can Dream of You,” which was written by brother Livingston and recorded on Liv’s 1973 release, “Over the Rainbow.”

Meanwhile, big changes were brewing on the business side of JT’s career – changes that would culminate in his jumping ship and leaving Warner Brothers for Columbia Records (later Sony) in December 1976. The move had many repercussions, but none bigger than Warner’s decision to milk their relationship with JT one last time with the release of a greatest hits collection. Of the 13 tracks selected, 10 came straight from his Warner releases, while “Something In the Way She Moves” and “Carolina In My Mind” from the Apple debut album were re-recorded. Finally, a new hard-rocking live version of “Steamroller” finished off the collection.

The result, 1976’s enormous seller “Greatest Hits,” was a huge final success to cap off the relationship with Warner Brothers. The album was certified Gold (500,000 copies) almost immediately and Platinum (1 million copies sold) a year later in November 1977. Then in 1999 it was one of the original 62 albums certified Diamond, a new designation by the Recording Industry Association of America for recordings that have sold more than 10 million copies. To this day “Greatest Hits” remains one of the best-selling albums of all time.

The relationship with Columbia began in earnest by mid-1977 with the June 24 release of “J.T.” “Handyman” (penned long before by Otis Blackwell and Jimmy Jones) earned JT his second “Best Pop Vocal Performance” Grammy and his second for a song he didn’t write. That mixed blessing wouldn’t come until the following February, though, and with the album’s release JT immediately set out on a 22-show tour in support of it while two singles, “Handyman” / “Bartender’s Blues” and “Your Smiling Face” / “If I Keep My Heart Out of Sight” were released by Columbia. A third single, “Honey Don’t Leave L.A.,” wasn’t released until January 1978. All the factors combined made for strong sales: “J.T.” went Gold within a month of its release and has sold more than 3 million copies to date.

Along with JT’s Grammy for “Handyman,” his producer and old friend Peter Asher picked up a “Producer of the Year Grammy.” Sister Kate Taylor’s second album hit stores, too. The self-titled release was produced by JT and included his composition “Happy Birthday Sweet Darling.”

1978 saw JT branching out into other musical genres, too, when he composed three songs for the Broadway musical “Working.” Based on Studs Terkel’s book by the same name, the short-lived production included JT’s “Millworker” and “Brother Trucker,” both of which he later recorded for the “Flag” album. He also composed the music for the Spanish-language song “Un Mejor Dia Vendra” for the play. Reviews were tepid, and “Working” quickly disappeared from the stage.

After the release of “Flag” in April 1979, JT and Carly played at “No Nukes,” a series of five anti-nuclear concerts by Musicians United for Safe Energy (MUSE). The shows were a great success and would become both a popular concert film and triple-length album. James continued to tour extensively, which reportedly didn’t sit well with Carly as she stayed home with their two kids. Nothing could stop JT from hitting the road, though, and the title of his 1981 album, “Dad Loves His Work” made it clear where his allegiances lay.

In 1982 the ten-year marriage came to an end and the two were divorced. JT continued to tour, but didn’t release another album until 1985’s “That’s Why I’m Here.” Earlier in the year he had performed at the enormous Rock In Rio concert in Brazil, which caused something of a midlife turnaround for JT and inspired the track “Only a Dream In Rio.” It also didn’t hurt that just after the album’s release JT married his second wife, actress Kathryn Walker.

Amid frequent touring JT released “Never Die Young” in 1988 and “New Moon Shine” three years later in 1991. That year also marked record label EMI’s re-release of JT’s self-titled debut album on CD for the first time, giving fans who may have missed the beginning of his career a chance to hear his early sound.

JT’s perennial summer tours were recorded and released as the popular double “(LIVE)” album in 1993, which broke up the drought of new material that would last until 1997. In the meantime, though, JT was hit by a string of tragedies including a divorce from Walker, the death of his longtime band member and friend Don Grolnick, and finally the death of his father Ike in November 1996.

“Hourglass” was released in May of 1997 and was JT’s biggest seller in many years, but the success was tempered by the sudden suicide death of his drummer Carlos Vega on the eve of a planned performance on the Oprah Winfrey Show. That appearance was cancelled, but the next month a big performance at New York’s Beacon Theatre went on with drummer Steve Jordan filling in. The show was broadcast live in PBS stations and later released as the hugely successful “James Taylor: Live at the Beacon Theatre” DVD.

After releasing an uninspired “Greatest Hits Volume 2” collection in 2000, JT continued to tour extensively. Then his personal life took center stage when in 2001 he married Carolyn “Kim” Smedvig. He’d met her while performing a symphonic show with the Boston Symphony Orchestra where Smedvig worked. But the wedding news was eclipsed only a few months later when JT surprised his fans by announcing the birth of twin sons, Henry and Logan, via a surrogate mother.

In August 2002 JT released “October Road,” a hugely successful album with strong sales and lots of media appearances. The album included a single Christmas song, “Have Yourself a Merry Little Christmas” – a track that gave fans a taste of the all-Christmas album that would come a few years later in 2004. He followed “October Road” with the release of “The Best of James Taylor,” a career-spanning collection that included a single new track, the John Sheldon-written song “Bittersweet.”

Now freed from his Sony contract obligations, JT recorded “James Taylor: A Christmas Album” exclusively for Hallmark stores. It was his first solo release outside the major record label system and seems to reflect an artist who’s lived most of his professional life within the confines of the corporate music industry and is willing to take risks with something new. It’s not clear yet whether the album is a permanent departure from major labels or just a one-time experiment, but either way JT’s career is still going strong.