Given the type of news coverage he gets, it may surprise you to learn that John Mayer is also a musician. His major-label debut, Room for Squares, came out in 2001, and within two years he was rewarded with his first Grammy win, followed by praise from every corner of the music industry, from blues masters (B.B. King and Eric Clapton) to rap stars (Kanye West and Jay-Z) to Nashville standouts (the Dixie Chicks and Brad Paisley). His gentle voice and introspective lyrics looked back to 1970s songwriters like James Taylor, and his guitar playing was versatile and masterful.
There hadn’t been a new solo male rock star in the music business since Lenny Kravitz, and Mayer fit the bill. He wrote hit songs—the ballads “Daughters,” which went to number one, “Your Body Is a Wonderland” and “Say,” the peppy and clever “No Such Thing,” the bluesy “Gravity” and the soulful “Waiting on the World to Change”—that were solidly constructed from warm sentiments and sophisticated music detail. He wrote “some of the most women—friendly anthems this side of Eve Ensler,” one journalist swooned. Not since Sting had a male singer been both so popular and so respected.
And so handsome, too. Mayer, a taut six-foot-three, was soon dating the kind of beauties who populate magazine covers: Jennifer Love Hewitt, Cameron Diaz and Minka Kelly, most recently seen on the arm of Derek Jeter. In 2006 he surprised some fans by dating Jessica Simpson, who seemed (musically at least) the antithesis of what he stood for. Alongside his music career he’s lately had a parallel life as a tabloid topic, due to his romance with actress Jennifer Aniston. They were together from April 2008 to March 2009, including a two-month breakup during their summer together. After he and Aniston split, Mayer released Battle Studies, the best record of his career, a set of related songs in which he mourns lost love, rejoices in his independence and castigates himself for romantic failure.