2006

John Mayer

December 31

Stepping Out with Jessica Simpson

New Year's Eve marks the unofficial coming out party for Jessica Simpson (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 tagging along on Mayer's tour, and Mayer tells Ryan Seacrest at the Grammy Awards – in Japanese – "She's a lovely woman and I'm glad to be with her."

2007

John Mayer

May 18

Breaking Up with Jessica Simpson

After months of together-time (including romantic trips to Australia and Rome), Mayer and Simpson break up – but remain in frequent email contact. They briefly reunite days later, but split for good in early June. Although both keep mum on the parting, Simpson admits to In Style, "I've had my heart broken since my divorce."

John Mayer

October

Friday Night Lovin'

After briefly spending time with Cameron Diaz, Mayer steps out with Friday Night Lights cheerleader Minka Kelly (right). The two refuse to speak publicly about their romance, but certainly log plenty of frequent flyer miles to be together: brunch in Austin, Texas, shopping in Santa Monica and courtside at a New York Knicks basketball game. They quietly split in January 2008.

2008

John Mayer

Spring

John & Jen's Hot Romance

While shooting the movie Marley & Me with Owen Wilson in Miami, Jennifer Aniston, 39, spends time with Mayer, 30. Paparazzi even snap photos of them embracing on a Miami beach. In August, their romance fizzles, but they briefly reunite before calling it quits after attending the Academy Awards together in 2009.

2009

John Mayer

February 08

Two More Grammys For Mayer

Nominated for five awards, Mayer picks up two trophies at the 51st Grammy Awards: Best Male Pop Vocal Performance for "Say" and Best Solo Rock Vocal Performance for "Gravity". "It’s always been an honor for being a musician," Mayer says of his win during his acceptance speech. The crooner also performs on the Grammy stage with legend B.B. King, Buddy Guy and country star Keith Urban in a tribute to Bo Diddley.

John Mayer

November 17

Ready for Battle

Mayer's latest studio album, Battle Studies, tops the Billboard albums chart. Rolling Stone praises Mayer in an album review, calling his latest release "a real study in craftsmanship and understated guitar ninja-dom."

2010

John Mayer

February

Mayer Kisses & Tells

After appearing on the cover of Rolling Stone, Mayer gets himself into hot water for using the N-word, commenting on breaking up with Jennifer Aniston, and comparing sex with Jessica Simpson to "crack cocaine" and "sexual napalm" in an interview in the March issue of Playboy. He later apologizes for his "arrogance," Tweeting, "I just wanted to play the guitar for people. Everything else just sort of popped up and I improvised, and kept doubling down on it."

2012

John Mayer

May 22

'Born' Again

After spending two years out of the spotlight, Mayer returns with his latest album, Born and Raised, which tops the Billboard 200 chart making it his third No. 1 album. "I hope people want to receive this music. I have so much that I need to say – I hope I get a chance to say it. I hope people are interested," he tells NPR of his return to music.

John Mayer

August

Road to Romance

Mayer, 34, and Katy Perry, 28, spark relationship rumors after being photographed leaving L.A.'s Chateau Marmont together. While the romance appears to cool off shortly after, the couple gives it another try, and later spends the holidays together. "They're happy together," says a source.

2013

John Mayer

March

Mayer of Splitsville

Only a month after Mayer tells CBS Sunday Morning that his relationship with Perry "feels like something that's very human," the couple calls it quits for the second time. But by July 4, the on-again, off-again pair appears to reconcile once more, with Perry sharing an affectionate photo of the two over Instagram.

Photo Credits

BIOGRAPHY (top to bottom): INF; Mike Hensen/AP; James Devaney/WireImage; Fame; Jason Merritt/Getty; amazon.com; Courtesy Rolling Stone Magazine; Xposure; SPW/Splash News Online

Edited by Julia Wang

John Mayer

Celebrity Central / Top 25 Celebs

 

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