After months of together-time (including and ), Mayer and Simpson – but . They days later, but in early June. Although both keep mum on the parting, Simpson, "I've had my heart broken since my divorce."
Breaking Up with Jessica Simpson
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Stepping Out With Jessica Simpson marks the unofficial coming out party for (right) and Mayer. But the love-connection doesn't sit well with some of Mayer's longtime supporters (What's an East Coast intellectual doing with Ms. Chicken-or-Fish?) "We had a blast that night," he tells Entertainment Weekly. "Some of my fans have been a little upset at me." Still, Simpson begins on Mayer's tour, and Mayer tells Ryan Seacrest at the Grammy Awards – – "She's a lovely woman and I'm glad to be with her."
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.
Lighting Strikes Thrice
The singer – who has appeared on Comedy Central'sChappelle's Show and filmed his own VH-1 comedy special – begins performing little-announced gigs at 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 the Comedian
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 .
Change of Direction
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 tellsRolling Stone that he thought the song was so sappy: "I saw it as career death."
No Sophomore Slump
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. 
Grammy Gold
Southern SojournAfter 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, InsideWants Out, and performs at the prestigious South by Southwest Music Festival in 2000, where he lands a contract with Columbia Records' Aware Records.
Big Break!Mayer releases his major-label debut, Room forSquares, 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."
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.
John Mayer's got five Grammy Awards, been dubbed a "guitar hero" by Rolling Stone, and released three platinum-selling albums, but it was a relationship with a little-known starlet by the name of Jessica Simpson that made him paparazzi material.
With his lanky 6'3" frame and puppy-dog eyes, the Connecticut-bred musician once told Entertainment Weekly, "I really don't want to be a hunk." But with hits like "Your Body is a Wonderland" and hook-ups with Jennifer Love Hewitt and Jennifer Aniston, Mayer's become a reluctant hottie. To his credit, Mayer has transitioned from pop poster boy to up-and-coming blues legend, and in 2007, Time magazine named him one of its 100 Most Influential People in the World, saying "This white boy has something to say about the blues."
In the 2000s no musician has been able to deftly navigate the terrain between R&B, pop, soul, and rock as successfully as John Mayer. Throughout his career his deference for music traditions, consummate musicianship, and keen sense of melody has kept him atop the charts and in constant radio rotation.
The middle son of two teachers who grew up in Fairfield, CT, John Mayer began playing guitar at age 13, and was soon playing local clubs in blues and cover bands. At 17, he was rushed to the hospital with cardiac arrhythmia, spending a week in bed; it was there, Mayer has said, that he began songwriting in earnest.A year after graduating high school, Mayer enrolled at Boston's Berklee College of Music; he soon skipped that to head to Atlanta to play coffeehouses with his friend Clay Cook as LoFi Masters. Shortly afterward, Mayer left to go solo, and by 1999 had cut an eight-song mini album he released and distributed himself, Inside Wants Out, hitting the road for a tour of the region around Georgia. He caught a break after appearing at 2000’s South by Southwest Music Festival in Austin, TX, and was signed to Aware, a Columbia subsidiary, and recorded Room for Squares (Number Eight, 2001), which was picked up for release by the senior label. Columbia worked Mayer steadily until, over the course of a year, he became ubiquitous, thanks to the singles “No Such Thing” (Number 13, 2002) and “Your Body Is a Wonderland” (Number 18, 2002). Columbia further cashed in by reissuing Inside Wants Out (Number 22, 2002).
After the stopgap live Any Given Thursday (Number 17, 2003), Mayer released his follow-up, Heavier Things (Number One, 2003), which yielded “Bigger Than My Body” (Number 33, 2003) and “Daughters” (Number 19, 2004). Another live disc, As/Is, followed in 2004. That year, Mayer began an improbable turnaround, edging his public image from strictly mama’s-boy to sly smart-aleck, thanks to his oft-sardonic blog posts, a column in Esquire magazine, and a memorable guest spot on The Chappelle Show, jamming in a Harlem barbershop with members of the Roots. He later guest-starred on “Go!” — the first single off rapper Common’s Be, produced by Kanye West.
In his own music, Mayer began to focus on meatier stuff, particularly the blues. He played shows with Buddy Guy and Herbie Hancock, and in November 2005 released Try! Live in Concert (Number 34), credited to the John Mayer Trio, with veteran sessionmen Steve Jordan on drums and Pino Palladino on bass; they opened for the Rolling Stones that October. Continuum (Number Two, 2006) followed a year later, and its quasi-protest number, “Waiting on the World to Change (Number 14, 2006), soon wormed its way into America’s collective ear much the way his earlier material had.
Mayer, who also dabbles in stand-up comedy, has been the subject of much tabloid fodder and romantically linked to pop singer Jessica Simpson and actress Jennifer Aniston. In the summer of 2008 Mayer released a live DVD/CD entitled Where the Light Is recorded at a December 2007 concert in Los Angeles.
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