John Mayer Trivia
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70 free John Mayer trivia questions with answers — music quiz, new questions added Aug 2026.
John Mayer has been three or four different musicians in one career: the acoustic singer-songwriter of the early 2000s, the blues-rock guitarist who formed a power trio and made Continuum, the Laurel Canyon-inflected songwriter who lost his voice and moved to Montana, and the guy who stepped into Jerry Garcia's spot in Dead & Company. This quiz covers all of them. You'll find the easy stuff, like his debut album, the Grammy-winning singles and the Katy Perry and Taylor Swift duets, alongside questions that only a real fan will land: which album blocked Continuum from number one, the pedal he single-handedly brought back, the name of his cruise-ship festival, and the Grateful Dead song that started everything. Every answer has been checked against the published record and each question links to its source, so it works for a fan-club night, a road trip playlist argument or a proper test of whether you actually know your Mayer.
30 of 70 questions with answers and explanations. Play the quiz
Q 01John Mayer grew up in Fairfield, Connecticut, but in which nearby city was he born?
Bridgeport
Bridgeport. Raised next door in Fairfield, he picked up the guitar at 13 and within a couple of years was already playing sets in the area's blues bars.
Q 02Which film performance first made a young John Mayer want to play guitar?
Michael J. Fox in Back to the Future
Michael J. Fox in Back to the Future. Marty McFly's 'Johnny B. Goode' at the school dance sent Mayer to guitar lessons, though Fox was miming: the singing voice belonged to session vocalist Mark Campbell.
Q 03Which future tennis star was Mayer's close elementary-school friend and after-school Nintendo partner?
James Blake
James Blake. They spent almost every afternoon for three years at Blake's house in Fairfield; Blake later walked away from Harvard as the top-ranked college player in the country to turn professional.
Q 04What put a 17-year-old Mayer in hospital for a weekend and, he says, awakened the songwriter in him?
An irregular heartbeat
An irregular heartbeat. Doctors diagnosed a cardiac arrhythmia, and the scare pushed him to write lyrics for the first time, 'with a depth I didn't even know I had as a person'.
Q 05Where did Mayer enrol as a student in 1997, only to leave within a year?
Berklee College of Music
Berklee College of Music. He went to Boston to sharpen his guitar playing, decided during his first year that songwriting was his real calling, and left to chase it.
Q 06With which fellow guitarist did Mayer leave college and form the duo Lo-Fi Masters?
Clay Cook
Clay Cook. The duo soon split, yet three songs they wrote together landed on Mayer's first album, including its breakthrough hit; Cook later joined the Zac Brown Band.
Q 07Which city did Mayer move to after quitting college, playing clubs such as Eddie's Attic?
Atlanta
Atlanta. He played anywhere that would have him, bookstores included, and his doubts about the move became 'Why Georgia', a song about what he called a quarter-life crisis.
Q 08What was the title of the independent EP Mayer released in 1999 before signing to a label?
Inside Wants Out
Inside Wants Out. He put the mostly acoustic EP out himself while playing clubs by night and mailing demo discs by day, then re-recorded four of its songs for his first album.
Q 09Which imprint first released John Mayer's debut album in 2001, before Columbia re-released it?
Aware Records
Aware Records. The label signed him after his South by Southwest set in 2000, and Columbia repackaged the album with an extra track for a national release later in 2001.
Q 10What is the title of Mayer's 2001 debut studio album?
Room for Squares
Room for Squares. The title flips saxophonist Hank Mobley's jazz album No Room for Squares, trading its hipper-than-thou exclusiveness for an open invitation.
Q 11Which song was Mayer's debut single, peaking at number 13 on the Billboard Hot 100?
No Such Thing
No Such Thing. Its lyric tells school-leavers there is no 'real world' to brace for, and Mayer had lived it: after graduating he put college off and took a job at a gas station.
Q 12Which song won Mayer his first Grammy, Best Male Pop Vocal Performance, in 2003?
Your Body Is a Wonderland
Your Body Is a Wonderland. Mayer has said he wrote it about his very first girlfriend, from when he was 14, and it beat entries by James Taylor, Elton John and Sting to the award.
Q 13Which actress, whom Mayer dated in 2002, denied his hit was about her, joking her body was 'more like a pawnshop'?
Q 21Which John Mayer song appears on Try!, Continuum and Where the Light Is, whose live version won a 2009 Grammy?
Gravity
Gravity. Mayer calls it the most important song he has ever written, a reminder to himself to keep his head on, and one he expects to 'grow up with me'.
Q 22Which Jimi Hendrix song did Mayer cover on Continuum?
Bold as Love
Bold as Love. It was the song the John Mayer Trio played at their first appearance, a televised benefit in January 2005, and the chemistry on it convinced the three to become a band.
Q 23The first two letters of the title on Mayer's Continuum cover merge to resemble what symbol?
An infinity sign
Jennifer Love Hewitt
Jennifer Love Hewitt. The dates back her up: the song was on an album released the year before they dated, and Mayer later called it the first of many songs wrongly pinned on a famous girlfriend.
Q 14In 2004 Mayer played a surprise three-song set at which event at Pennsylvania's Pennsbury High School?
The senior prom
The senior prom. Class president Bob Costa had spent two years campaigning to land him, and the students walked in with no idea that he was on his way.
Q 15Which 2003 album became Mayer's first to debut at number one on the Billboard 200?
Heavier Things
Heavier Things. Its instant success reversed the story of his debut, a slow burner that was out for almost a year before going platinum and never climbed past number eight.
Q 16Which Mayer song won the Grammy for Song of the Year in 2005?
Daughters
Daughters. Mayer has said it came from loving a woman who could not trust men, a wound he traced back to the first man in her life, her absent father.
Q 17Who played bass in the John Mayer Trio alongside drummer Steve Jordan?
Pino Palladino
Pino Palladino. He was a late stand-in: Willie Weeks could not make a 2005 benefit telethon, Jordan phoned Palladino, and the three clicked so quickly that they became a band.
Q 18Which band did the newly formed John Mayer Trio open for on three East Coast dates in October 2005?
The Rolling Stones
The Rolling Stones. The blues trio joined the A Bigger Bang tour within months of forming, and in 2012 the Stones brought Mayer back as a guest at a 50th-anniversary show in Newark.
Q 19Which artist's album kept John Mayer's Continuum from debuting at number one on the Billboard 200 in September 2006?
Justin Timberlake
Justin Timberlake. FutureSex/LoveSounds reached US shops the same day and sold more than twice as many copies that week, so Continuum had to settle for number two.
Q 20Which Continuum single won Mayer Best Male Pop Vocal Performance at the 2007 Grammys?
Waiting on the World to Change
Waiting on the World to Change. When Mayer handed the album in he was told it had no hits, cried, and vowed to quit for design school; its first single then won him this Grammy.
An infinity sign. More than a year before the album came out, Mayer wrote in a magazine column that he was 'obsessed with time lately' and working out where he stood 'in the continuum'.
Q 24Which road standard did John Mayer record for Pixar's Cars, alongside Rascal Flatts' 'Life Is a Highway'?
Route 66
Route 66. The film is set in a town on that very highway, bypassed by the interstate, so Pixar used the song twice: Chuck Berry's 1961 recording and Mayer's Grammy-nominated new one.
Q 25Mayer's 2007 ballad 'Say' was written for which Rob Reiner film?
The Bucket List
The Bucket List. Mayer wrote it to order for the film's story of two terminally ill men and their wish list, and the single was then added to a reissue of his album Continuum.
Q 26Which Tom Petty song does Mayer play as an acoustic cover in the concert film Where the Light Is?
Free Fallin'
Free Fallin'. Mayer's live acoustic version was released as a single and carried Petty's 1989 hit back into the Hot 100 in July 2008, almost two decades after it first charted.
Q 27Which song was the first single from Mayer's Battle Studies (2009), noted for its open reference to drug use?
Who Says
Who Says. It opens by asking who says he can't get stoned, yet Mayer maintained the song was about freedom rather than marijuana: 'being in control of the pleasure in your life'.
Q 28Mayer wanted Taylor Swift to play which singer to his Tom Petty on their 2009 duet?
Stevie Nicks
Stevie Nicks. He woke up three days running with the song idea in his head, and called the finished track his love letter to the sound of Tom Petty and Fleetwood Mac.
Q 29Which Battle Studies single features Taylor Swift on vocals?
Half of My Heart
Half of My Heart. Explaining his choice of duet partner to MTV News, Mayer said he had thought: 'This Taylor Swift girl is going to be around for a long time.'
Q 30What medical problem delayed Born and Raised and forced Mayer to cancel its 2012 tour?
A granuloma on his vocal cords
A granuloma on his vocal cords. When surgery failed, a UCLA specialist paralysed the cords with heavy doses of Botox so they could heal, and Mayer went months without saying a word.