James Taylor
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50 free James Taylor trivia questions with answers — music quiz, new questions added Oct 2026.
James Taylor has been one of the defining voices of American songwriting for more than half a century. His warm baritone and fingerpicked guitar made confessional songs a mainstream sound at the start of the 1970s, and the story behind them is as dramatic as any in rock: a troubled adolescence, a lucky break in London, addiction, recovery and a late-career run that few of his peers can match. This quiz covers all of it. You will find questions on the hit singles and what inspired them, the covers he made his own, the famous friends who sang and played on his records, his albums and labels, and his life away from the stage, from a North Carolina childhood to the Berkshires. A handful look at his surprise appearances in film and on television, and at the honours that have come his way. The questions about songs ask about the stories, people and places behind the words rather than quoting them, so they suit casual listeners as well as fans who know every album. Each answer comes with a short explanation, so you will pick up something new whether you score five or fifty.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which songwriter wrote You've Got a Friend, the ballad that gave James Taylor a US number-one single in 1971?
Carole King
Carole King wrote it and put her own version on Tapestry the same year. At the 1972 Grammys she won Song of the Year for it while he took the male pop vocal award.
Q 02Which 1970 James Taylor hit reflects on a friend's suicide, his own addiction and the collapse of his New York band?
Fire and Rain
Fire and Rain became his first US top-ten hit, and he has said he wrote it in three parts, the last about coming to grips with fame and fortune.
Q 03Which singer-songwriter married James Taylor in her Manhattan apartment in 1972 and later scored duet hits with him?
Carly Simon
Carly Simon and he saw an after-show party at Radio City Music Hall turn into their wedding reception, and their children Sally and Ben both grew up to be musicians.
Q 04Which star inducted James Taylor into the Rock and Roll Hall of Fame, decades after playing on his debut album?
Paul McCartney
Paul McCartney played bass on Carolina in My Mind in 1968, with George Harrison adding uncredited backing vocals, and did the honours at the 2000 ceremony.
Q 05Which superstar sang James Taylor's blues parody Steamroller on the live album of a satellite concert from Hawaii?
Elvis Presley
Elvis Presley made a single of a song James Taylor had written to mock the pompous white blues bands he kept hearing in Greenwich Village.
Q 06In which animated series does James Taylor play himself, singing to astronauts from mission control?
The Simpsons
The Simpsons cast him in the episode Deep Space Homer beside Buzz Aldrin, and his face later turned up as the missing last piece of the family's jigsaw puzzle.
Q 07Which Pixar film features James Taylor singing Our Town, a Randy Newman ballad that earned an Oscar nomination?
Cars
Cars won Randy Newman a Grammy for the song, though the Oscar itself went to a track from the climate documentary An Inconvenient Truth.
Q 08Which president gave James Taylor the Medal of Freedom after the singer had played free campaign concerts for him?
Barack Obama
Barack Obama presented the medal in 2015, having had James Taylor sing America the Beautiful at his second inauguration in 2013.
Q 09Which record label made James Taylor its first non-British signing in 1968 after hearing his demo tape in London?
Apple
Apple was the Beatles' own new label, and his sessions overlapped with the White Album, so some studio time booked for the band went to his record instead.
Q 10James Taylor wrote the cowboy lullaby Sweet Baby James for which newborn relative, who had been named after him?
His nephew
His nephew was the baby son of his older brother Alex, and the tune came to him on a drive through Carolina to meet the child for the first time.
Q 11Which Inez and Charlie Foxx tune did James Taylor and his first wife turn into a top-five duet in 1974?
Mockingbird
Mockingbird was his idea. He had watched the Foxx siblings perform it at the Apollo Theater in 1965 and used to sing it for fun with his sister Kate.
Q 12Which Jimmy Jones hit did James Taylor slow right down for a 1977 single that won him a second Grammy?
Handy Man
Handy Man had already charted for Del Shannon in 1964, and James Taylor's drowsy remake turned the brisk original into a ballad that reached number one in Canada.
Q 13Which Motown singer first recorded How Sweet It Is, the song James Taylor took into the US top five in 1975?
Marvin Gaye
Q 21Which album finally gave James Taylor a number one on the Billboard 200, some 47 years after his debut?
Before This World
Before This World ended a wait for the top spot that only Tony Bennett had exceeded, and it came after 11 of his earlier albums had reached the top ten.
Q 22Which James Taylor album made him the first act with a US top-ten album in each of six consecutive decades?
American Standard
American Standard, his 2020 album of covers, debuted at number four and went on to win the Grammy for best traditional pop vocal album.
Q 23Which label did James Taylor join in 1977 after leaving Warner Bros., staying for more than a quarter of a century?
Columbia
Marvin Gaye cut the original in 1964, and James Taylor's version, with his then-wife on harmony vocals, is still the most successful remake of it.
Q 14Which 1962 Drifters hit did James Taylor remake as the lead single from his 1979 album Flag?
Up on the Roof
Up on the Roof gave him a top-30 single, and he later singled it out as the remake that had brought him particular satisfaction.
Q 15Which songwriter, then romantically linked to James Taylor, sang backing vocals on his hit You've Got a Friend?
Joni Mitchell
Joni Mitchell also had him play acoustic guitar on three tracks of Blue, the album she made during their intense romance.
Q 16Which short-lived band did James Taylor form in New York with his friend Danny Kortchmar before finding fame solo?
The Flying Machine
The Flying Machine broke up after a three-week stay at a failing nightspot in the Bahamas for which the players were never paid.
Q 17Which former British pop star signed the unknown James Taylor in 1968 and then became his manager and producer?
Peter Asher
Peter Asher, once half of the duo Peter and Gordon, went on to shape the 1970s California rock sound and twice won the Grammy for Producer of the Year.
Q 18In which 1971 road movie did James Taylor star as a street racer alongside Beach Boys drummer Dennis Wilson?
Two-Lane Blacktop
Two-Lane Blacktop cast him after its director spotted his face on a Sunset Strip billboard, and he played a character known only as the Driver without ever reading the script.
Q 19James Taylor grew up in which North Carolina college town, where his father became dean of the medical school?
Chapel Hill
Chapel Hill became home in 1951, though his father Isaac was often away, including a spell in Antarctica with the Navy's Operation Deep Freeze.
Q 20What kind of accident on Martha's Vineyard broke both of James Taylor's hands and feet just as his career was starting?
A motorcycle crash
A motorcycle crash stopped him playing for several months, shortly after he had closed the 1969 Newport Folk Festival before thousands who stayed on through a downpour.
Columbia kept him until he chose not to renew in 2004, while Warner marked his departure with a Greatest Hits set that has sold 11 million copies in the US.
Q 24A huge festival crowd in which city in 1985 lifted James Taylor at a time when he was thinking of retiring?
Rio de Janeiro
Rio de Janeiro put him before some 300,000 people who knew his songs in detail, and he said the welcome helped get him back on track.
Q 25Which West Hollywood club hosted James Taylor's 2007 reunion with his original band, later issued as a live album?
The Troubadour
The Troubadour was marking its 50th anniversary with those six shows, and he had headlined there as a newcomer back in July 1969.
Q 26Which music legend played harmonica on James Taylor's 1997 album Hourglass, two decades after writing a song with him?
Stevie Wonder
Stevie Wonder guested on the single Little More Time with You, and back in 1976 the pair had written Don't Be Sad 'Cause Your Sun Is Down together.
Q 27The death of which comedian, a friend of James Taylor, helped spur the singer to finally give up heroin in 1983?
John Belushi
John Belushi's death and a wish to be a better father to Sally and Ben led him to come off methadone over four months starting in September 1983.
Q 28James Taylor joined Bruce Springsteen and the Doobie Brothers in New York in 1979 for concerts opposing what?
Nuclear power
Nuclear power was the target of Musicians United for Safe Energy, formed soon after the Three Mile Island accident, and the shows became the album and film No Nukes.
Q 29Which Massachusetts music venue, long a summer stage for James Taylor, honoured him with its own medal in 2024?
Tanglewood
Tanglewood is the Boston Symphony Orchestra's summer home in the Berkshires, and Taylor Swift, who was named after him, joined him on its stage as a guest in 2012.
Q 30Which US Secretary of State invited James Taylor to Paris to sing You've Got a Friend after terror attacks there?
John Kerry
John Kerry and the mayor of Paris hosted him at the Hôtel de Ville in January 2015, where he played an acoustic version in tribute to the victims of that month's attacks.