A soulful singer to the core, John Mayer had a gift of writing sharp lyrics and a deft command of the guitar that was reminiscent of renowned blues guitarists like Eric Clapton and Buddy Guy. The Grammy Award-winning singer burst onto the pop scene with the album Room for Squares (2001), and easily made his mark as a sensitive crooner having a "quarter-life crisis" with songs such as "No Such Thing" and "Your Body Is a Wonderland." Mayer's follow-up albums, Heavier Things (2003) and Continuum (2006), featured ballads like "Daughters" that displayed the acoustic rocker's vulnerabilities, as well as his reflections on bigger political and social issues like "Waiting on the World to Change." Yet, just a few years after scoring his first hit, Mayer quickly became a tabloid fixture for his serial dating habits. His conquests reportedly included some of Hollywood's most coveted beauties, but none were more salacious than his on-again-off-again trysts with singer Jessica Simpson and actress Jennifer Aniston. Mayer landed in hot water after his shocking kiss-and-tell-all in a Playboy magazine interview, where he compared having sex with Simpson to craving crack cocaine and detailed the reason behind his split with Aniston. After a public flap over his controversial interview, Mayer tried to redeem himself by bringing the focus back to music. In 2009, he released the commercially successful album pop-rock Battle Studies, featuring openhearted lyrics and brilliant guitar-shredding skills that reminded everyone that Mayer was still one of the most dynamic and exciting musicians of all time.