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1990s

Varsity Blues

"I went to school to get it over with," John Mayer, the middle son of Richard (a high school principal) and Margaret (a teacher), tells ABC News in 2003. "I remember asking my mom, 'Mom, will you please let me drop out?'" (He'll later capture that angst in his breakthrough hit, "No Such Thing"). After graduation, Mayer spends 15 months working as a full-service gas station attendant for $7 an hour, and uses the cash to buy a guitar.

1998

John Mayer

Southern Sojourn

After two semesters at Boston's Berklee College of Music, Mayer drops out to pursue music and relocates to Atlanta, Georgia. "Atlanta's my musical home," he says in 2003. "It really was the place where I really came alive." He becomes a frequent performer at local blues clubs, self-releases his first album, Inside Wants Out, and performs at the prestigious South by Southwest Music Festival in 2000, where he lands a contract with Columbia Records' Aware Records.

2001

John Mayer

Big Break!

Mayer releases his major-label debut, Room for Squares, prominently featuring Mayer's fetching face on the cover. It climbs to No. 8 on the Billboard 200 and sells more than 4 million copies on the strength of such singles as "No Such Thing" and "Your Body is a Wonderland."

2002

John Mayer

Enter Jennifer Love

Mayer gets his muse when he meets actress Jennifer Love Hewitt. The two begin an intense – but brief – relationship. "It was a strange little detour that I took for a minute," he tells EW, admitting he had been "madly in love." "It sucks. Because the idea of it was fantastic. It just didn't work." As for the rumor that "Your Body is a Wonderland" is an ode to Hewitt? Not so, she insists to PEOPLE. "John would have written, 'Your body is a disaster.'"

2003

John Mayer

February 23

Grammy Gold

Mayer accepts the Grammy for Best Male Pop Vocal Performance for "Your Body is a Wonderland," saying, "This is very, very fast and I promise to catch up." Though endearingly self-deprecating, it's a comment Mayer regrets. "I should have said something different," he tells ABC News days later.

John Mayer

September 09

No Sophomore Slump

Mayer's latest album, Heavier Things, hits No. 1 on the Billboard 200. Though his sentimental ballad, "Daughters," earns him two Grammys (Best Male Pop Vocal Performance and Song of the Year), Mayer tells Rolling Stone that he thought the song was so sappy: "I saw it as career death."

2005

John Mayer

Change of Direction

Mayer says "Daughters" "pigeonholed" him, so he makes an unexpected move when he forms a bluesy, guitar-driven jam band, The John Mayer Trio (right), with bassist Pino Palladino (who'd toured with The Who) and drummer Steve Jordan (who'd recorded with Mayer's hero Eric Clapton and Bob Dylan). After releasing Try! with the trio, he begins a series of collaborations with everyone from B.B. King to Alicia Keys.

2006

John Mayer

John Mayer the Comedian

The singer – who has appeared on Comedy Central's Chappelle's Show and filmed his own VH-1 comedy special – begins performing little-announced gigs at stand-up comedy venues in L.A. and New York. "Everyone connected to my well-being and on my payroll says stand-up is terrible," he tells Rolling Stone (which puts him on the cover as one of the generation's "New Guitar Gods"). "When I say, 'I'm doing stand-up tonight,' they hear, 'I'm going to start heroin.'" His frequently risqué routines get Mayer in trouble, most notably when reports surfaced that he'd used the n-word on stage.

John Mayer

September 12

Lighting Strikes Thrice

Mayer releases Continuum, which includes the protest anthem "Waiting on the World to Change." The CD becomes Mayer's third studio album to go platinum, and Rolling Stone says it "deftly fuses his love for old-school blues and R&B with his natural gift for sharp melodies and well-constructed songs." He wins two Grammys for Best Male Pop Vocal Performance and Best Pop Vocal Album.

John Mayer

October 11

Grin and 'Bear' It

Mayer, a notorious jokester, takes aim at Sheryl Crow (right) during their joint tour. For their second-to-last show, he comes onstage during her performance wearing a bear costume. Afterward, he writes on his blog, "This incredible six-week experience will be summed up with just a photograph: Sheryl Crow leaning against a [schmuck] in a bear suit." Crow gets her revenge at the next show, popping up in a bikini.

Photo Credits

BIOGRAPHY (top to bottom): amazon.com; amazon.com; Bauer Griffin; Steve Granitz/WireImage; amazon.com; James Devaney/WireImage; amazon.com; Jean Baptiste Lacroix/Wireimage

Edited by Julia Wang

John Mayer

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