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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 01In which Connecticut city was John Mayer born in 1977?
Bridgeport
His father was the principal of the local Central High School and his mother taught middle-school English. He grew up in nearby Fairfield.
Q 02Which film performance first made a young John Mayer want to play guitar?
Michael J. Fox in Back to the Future
Marty McFly's school-dance guitar scene did it. His father rented him a guitar when he turned 13, and a neighbor's Stevie Ray Vaughan cassette then pulled him toward the blues.
Q 03Which future tennis star was Mayer's close elementary-school friend and after-school Nintendo partner?
James Blake
Both grew up in Fairfield, Connecticut. Mayer's parents were so worried about his single-minded guitar obsession that they twice took him to a psychiatrist, who pronounced him healthy.
Q 04Mayer says the songwriter in him was born the night he left hospital at 17. What had put him there?
An irregular heartbeat
He was hospitalised for a weekend with cardiac dysrhythmia and wrote his first lyrics that same night. Panic attacks followed soon after, which he still manages with medication.
Q 05Where did Mayer enrol as a student in 1997, only to leave after two semesters?
Berklee College of Music
He had considered skipping college altogether, but his parents talked him into it. He lasted two semesters before heading south to chase gigs.
Q 06With which fellow guitarist did Mayer leave college and form the duo Lo-Fi Masters?
Clay Cook
Cook later joined the Zac Brown Band, and he co-wrote several early Mayer songs, including the breakthrough single. They split over Mayer's drift toward pop.
Q 07Which city did Mayer move to in 1997 to launch his career, playing venues like Eddie's Attic?
Atlanta
The Georgia capital became his adopted hometown, and his first Martin signature acoustic was limited to a run matching one of the city's area codes.
Q 08What was the title of the independent EP Mayer released in 1999 before signing to a label?
Inside Wants Out
The eight-song EP was later reissued by Columbia in 2002. Four of its songs were re-recorded for his major-label debut, including the opener 'Back to You'.
Q 09Which imprint first released John Mayer's debut album internet-only in 2001, before Columbia re-released it?
Aware Records
A lawyer acquaintance sent Mayer's EP to Aware's Gregg Latterman. Aware's deal with Columbia gave the major label first pick of its artists.
Q 10What is the title of Mayer's 2001 debut studio album?
Room for Squares
The Columbia re-release added the track '3x5' and updated artwork. Word of mouth and relentless touring pushed it to number one on Billboard's Heatseekers chart by March 2002.
Q 11Which song was Mayer's debut single, peaking at number 13 on the Billboard Hot 100?
No Such Thing
Its high school in Fairfield refused to let him film the video there because of the lyrics' digs at the school and its faculty. It stayed his highest-charting single until 'Say' in 2008.
Q 12Which song won Mayer his first Grammy, Best Male Pop Vocal Performance, in 2003?
Your Body Is a Wonderland
In his acceptance speech he said 'This is very, very fast, and I promise to catch up.' Blender later put the song at number 28 on its list of the 50 Worst Songs Ever.
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
Mayer has called it the most important song he has ever written and says the idea came to him in the shower. He performed it at the 2007 Grammys in a medley with Corinne Bailey Rae and John Legend.
Q 22Which Jimi Hendrix song did Mayer cover on Continuum, his first Hendrix cover on a studio release?
Bold as Love
He had played it live many times before, including on the televised Tsunami Aid concert.
Q 23The letters 'C' and 'o' on the Continuum album cover were customised to resemble what symbol?
An infinity sign
Jennifer Love Hewitt
She told Entertainment Weekly there were 'a lot of interesting things put together' but 'at first glance, not so much.' Mayer has never confirmed who the song was about.
Q 14Mayer's live CD/DVD Any Given Thursday was recorded in September 2002 in which city?
Birmingham, Alabama
The set at Oak Mountain Amphitheater included covers of Stevie Ray Vaughan's 'Lenny' and The Police's 'Message in a Bottle', and reached number 17 on the Billboard 200.
Q 15Which 2003 album became Mayer's first to debut at number one on the Billboard 200?
Heavier Things
It sold over 317,000 copies in its first week. Its lead single, 'Bigger Than My Body', opened with a riff generated by an Adrenalinn effects processor designed by Roger Linn.
Q 16Which Mayer song won the Grammy for Song of the Year in 2005?
Daughters
He dedicated the award to his grandmother, Annie Hoffman. Years later he told Ellen DeGeneres that Alicia Keys' 'If I Ain't Got You' should have won, and he sawed the trophy in half and gave her the top.
Q 17Who played bass in the John Mayer Trio alongside drummer Steve Jordan?
Pino Palladino
Mayer met both musicians through studio sessions and formed the blues-rock trio in spring 2005, announcing he was 'closing up shop on acoustic sensitivity'.
Q 18The John Mayer Trio's live album Try! was recorded at the House of Blues in which city?
Chicago
The 2005 set leaned on blues rather than adult-contemporary pop and included covers of Jimi Hendrix's 'Wait Until Tomorrow' and Ray Charles' 'I Got a Woman'. It was nominated for Best Rock Album.
Q 19Which artist's album kept Continuum from debuting at number one on the Billboard 200 in September 2006?
Justin Timberlake
Continuum entered at number two with 300,186 copies, blocked by FutureSex/LoveSounds. It has since sold over five million copies worldwide.
Q 20Which lead single from John Mayer's Continuum won Best Male Pop Vocal Performance at the 2007 Grammys?
Waiting on the World to Change
Columbia thought the album had no hits and pushed Mayer to write it. He has since admitted it is the song he least enjoys performing live.
Mayer had settled on the title a year before release, writing in a magazine column that he was 'obsessed with time lately'.
Q 24Which standard did John Mayer cover for Pixar's Cars (2006), earning a Grammy nomination?
Route 66
The nomination was one of five he received that December, alongside Album of the Year for Continuum and Best Rock Album for the Trio's Try!
Q 25Mayer's 2007 ballad 'Say' was written for which Rob Reiner film?
The Bucket List
It was his first commercial single not originally on one of his albums, and it earned him a record-tying fourth Grammy for Best Male Pop Vocal Performance.
Q 26The 2008 concert film Where the Light Is documents a December 2007 show at which venue?
Nokia Theatre L.A. Live
Directed by Danny Clinch, it moves through an acoustic set, a Trio blues set and a full-band set. It also captured his acoustic cover of Tom Petty's 'Free Fallin''.
Q 27Which song was the first single from Battle Studies (2009), noted for its open reference to drug use?
Who Says
It was his first studio single since 'Say' in 2007. Battle Studies debuted at number one and its arena tour grossed 45 million dollars, though Mayer later said it was not his best album.
Q 28The Battle Studies opener 'Heartbreak Warfare' was featured in which 2010 comedy?
Date Night
Steve Jordan co-produced the album, which was recorded partly at a Calabasas studio also named Battle Studies.
Q 29Which Battle Studies single features Taylor Swift on vocals?
Half of My Heart
Mayer was nominated for a Grammy for his solo version. Swift's 2010 song 'Dear John' was widely read as being about him, and Mayer told Rolling Stone it 'humiliated' him.
Q 30What medical problem delayed Born and Raised and forced Mayer to cancel its 2012 tour?
A granuloma on his vocal cords
Two surgeries failed, so a UCLA surgeon paralysed his vocal cords with high-dose Botox to let the growth heal. He went months unable to speak, typing on a Bluetooth keyboard for others to read aloud.