Only a few months after landing his big break, John Mayer performed at the 2001 Music Midtown Festival in Atlanta, Georgia.
Jumping ahead to 2006, John's fame continued to rise with sold out shows across the world.
From August 2006 to May 2007, John Mayer dated the beautiful Jessica Simpson. While the two are cordial today, things got heated after John's revealing interview with Playboy Magazine.
After his breakup with Jessica Simpson, the rocker chopped off his hair for a new spiky 'do.
John Mayer didn't wait long to jump back into the dating world as he romanced Minka Kelly from September 2007 to January 2008.
What was John's post-breakup transformation? Adding a sleeve to his set of tattoos!
Sleek, chic and sexy—our favorite John Mayer look to date!
Leave it to John for a bold beauty move. Are you a fan of his buzz cut and mustache?
The iconic Vanity Fair Oscar Party was the singer's first official red carpet with then girlfriend, Jennifer Aniston. After 11 months together, the couple called it quits in March 2009.
After working together on "Half Of My Heart" for John's Battle Studies album, the star fell head over heels for Taylor Swift in July 2010. We all know how their relationship turned out...with Taylor writing an award winning track about their relationship!
In February 2011, a goatee and long curly locks were the rocker's latest accessories.
In mid 2011, John once again mixed up his style by incorporating pieces inspired by his new Montana home.
June 2012 was a special month for John as he began dating his current girlfriend, Katy Perry. While the two spent some time apart, the lovebirds now seem more in love than ever!
John's latest outing? The hottie has been touring for his new album Paradise Valley! Stay tuned to OKMagazine.com for all the latest updates on our favorite guy.