After 10 months, he discharged himself and went to New York, where Kortchmar was putting together the Flying Machine. The group played Greenwich Village coffee-houses and recorded two Taylor originals, “Night Owl” and “Brighten Your Night With My Day,” before breaking up. Their demo tape was released as an album after Taylor became popular. One reason for the group’s breakup was Taylor’s addiction to heroin.
In early 1968 he went to England, and in London he recorded a tape of his material and sent it to Peter Asher. As an A&R man for the Beatles’ Apple Records, Asher encouraged Paul McCartney to sign him.
In mid-1968 Taylor recorded his debut album in London; Asher produced and McCartney and George Harrison sat in on one cut. The LP attracted little attention, and Taylor, still hooked on heroin at the end of the year, returned to America and signed himself into another mental institution.
During Taylor’s five-month stay, with Apple in disarray, Asher — who became Taylor’s producer and manager — negotiated a contract between Taylor and Warner Bros. Before Taylor was released, his solo stage debut at L.A.’s Troubadour had been arranged. From there he went to the Newport Folk Festival, where he met Joni Mitchell (she sang on Mud Slide Slim, and he played guitar on her autobiographical Blue).
Taylor and Asher rounded up Kortchmar, bassist Lee Sklar, drummer Russ Kunkel, and pianist Carole King to back him on his second album. Sweet Baby James attracted little attention initially, but “Fire and Rain” became a Number Three hit. Sweet Baby James reached the Top 10 in November 1970 and stayed on the LP chart into 1972. Taylor’s Apple debut was rereleased, entering the charts in October with the single “Carolina in My Mind.” Taylor appeared on a March 1971 cover of Time magazine, which hailed his ascent to stardom as a turn toward maturity and restraint in pop music, but at the same time publicized his drug abuses and other skeletons in his and his family’s closet. The article also alluded to a possible dynasty of Taylor-made pop stars. Livingston Taylor had launched his singing and songwriting career before his older brother had become famous, but Alex and Kate, while unquestionably musical, found less success.
Within two months of its release, Mud Slide Slim was the nation’s Number Two album. Taylor’s version of Carole King’s “You’ve Got a Friend” hit Number One in 1971, the same year that King’s version came out on Tapestry. That year Taylor co-starred with Dennis Wilson of the Beach Boys in the film Two-Lane Blacktop.
Then, almost as suddenly as he had emerged into public attention, he retreated from it. Except for a few benefit concerts for George McGovern’s 1972 presidential campaign, Taylor did not perform for another three years. He married Carly Simon in November 1972. Taylor continued to make and sell albums, but he didn’t score a Top 10 single between “You’ve Got a Friend” and 1975. (“Mockingbird,” a duet, was released by Simon in 1974.) One Man Dog (Number Four, 1973) contained “Don’t Let Me Be Lonely Tonight” (Number 14, 1973); Walking Man (Number 13, 1974) boasted no hit singles.
A month-long tour in 1974 signalled Taylor’s re-emergence. He returned to the charts with Gorilla (Number Six, 1975). Taylor’s cover of “How Sweet It Is (To Be Loved by You)” hit Number Five in 1975. JT, including a Top 5 cover of the Jimmy Jones–Otis Blackwell “Handy Man,” was Taylor’s first release on Columbia. Greatest Hits (Number 23, 1976), for which he rerecorded “Carolina in My Mind” and “Something in the Way She Moves,” fulfilled his obligations to Warners. It would go on to sell over 11 million copies. He signed Columbia’s lucrative contract before Hits was released. The double-platinum JT (Number Four, 1977) also marked Asher’s return as producer.
Taylor’s albums since JT have not quite repeated its success — Flag and Dad Loves His Work both hit Number 10 — but they have sold consistently. In 1978 he joined Paul Simon and Art Garfunkel on a Top 20 cover of Sam Cooke’s “Wonderful World,” released by Garfunkel. In 1979 he wrote a couple of songs for a Broadway musical, Working. Flag yielded a Top Thirty hit with Taylor’s typically understated cover of the Brill Building classic “Up on the Roof.” Taylor continued to support a variety of causes with benefit concerts. He campaigned for Jimmy Carter in 1976 and for John Anderson in 1980; in 1979 he participated in the MUSE antinuclear rally concerts at Madison Square Garden and appeared in the concert film No Nukes.
Taylor’s 1981 album, Dad Loves His Work yielded a hit single duet with J.D. Souther, “Her Town Too” (Number 11), released amid rumours that his marriage to Simon was ending. In 1982 Simon sued Taylor for divorce. From 1982 through 1985 Taylor toured the globe, with a band featuring Little Feat’s Bill Payne on piano. That’s Why I’m Here (Number 34, 1985), with guests including Joni Mitchell, Don Henley, and Graham Nash, yielded only a minor hit single in a cover of Buddy Holly’s “Everyday” (Number 61, 1985). In December 1985 Taylor wed for the second time, to Kathryn Walker. He continued touring extensively between albums that remained popular — 1991’s New Moon Shine (Number 37), for instance, sold over a million copies.
The mid-Nineties were a time of personal trial for Taylor, who lost his brother Alex to alcoholism in 1994 and divorced Walker in 1996. His first studio album in six years, Hourglass (Number Nine, 1997) was yet another platinum success and went on to win the Grammy for Best Pop Album, showing that the singer/songwriter remained impervious to the vagaries of musical trends. Taylor, who has been clean and sober since 1984, married Carolyn Smedvig in 2001. He was inducted into the Rock and Roll Hall of Fame in 2000.
In 2008, Taylor released Covers, an album of classics by the likes of Leonard Cohen, Buddy Holly and Eddie Cochran. In the summer of 2010 he launched a co-headlining tour arena with old friend Carole King.
One of the most successful touring solo acts of the past forty years, Taylor summed up his philosophy nicely on his 1985 song “That’s Why I’m Here”. “Fortune and fame’s such a curious game/Perfect strangers can call you by name/Pay money to hear ‘Fire and Rain’ again and again and again…I break into a grin from year to year /And suddenly it’s perfectly clear/That’s why I’m here.