Playboy Interview: John Mayer

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.

Mayer grew up in Fairfield, Connecticut, the second of three boys raised by Margaret, an English teacher, and Richard, a high school principal 19 years older than his wife. John’s guitar prowess led him to the Berklee College of Music, which he left after two semesters to begin a career in Atlanta. He suffered from panic attacks as well as acne “so bad that I would cancel dates and plans and stay in the house,” he has said.

He is beloved (though not universally) as one of the few uncensored stars, speaking with wit and impetuousness. He fills his Twitter feed with quips and advice, returning often to a few favorite topics: his dreams, his love of pie, Miley Cyrus songs and farting. Mayer has been “creating a new paradigm of fame,” veteran music blogger Bob Lefsetz wrote. As another journalist puts it, “Mayer takes self-awareness to new postmodern heights,” like a football player who provides “color commentary on his own career.”

Playboy contributing editor Rob Tannenbaum met with Mayer twice: first at the singer’s nearly unfurnished $7.5 million seven-bedroom villa in a gated community outside L.A., where Mayer poured glasses of 16-year-old Lagavulin neat; and then over lunch in Brooklyn a few hours before he played a secret MySpace show. Tannenbaum reports, “John Mayer talks the way he plays guitar solos--the words tumble out fast, like notes, and he may go on for as long as five minutes. He’ll jump out into different themes and suddenly slip in a new idea, but he always returns to his initial theme. He’s a prodigious talker, and he always brought up touchy subjects--his relationships with Simpson and Aniston, or his reputation as a douche bag--before I mentioned them, to show he wasn’t afraid to address them. From his soft-spoken songs you can’t tell how stubborn and defiant he is. Or how much he loves talking about sex. Or how mischievous he is. When I met him in the kitchen of his L.A. home he was talking about not talking anymore: ‘I think the world would be better off if I stopped doing interviews,’ he said. So we started there.”

Playboy: Is this the last John Mayer interview?

Mayer: No, though I have fantasies of it. And that doesn’t come out of pretension or laziness. It’s difficult for me to explain my life to someone without sounding like I’m complaining, which I’m not. I have no problem saying I’m in a bit of a strange time in my life.

Playboy: What’s strange about this time in your life?

Mayer: In one way or another, people probably know my name now. I’m squarely nestled in the crosshairs of their criticism and media reproach. I originally played music because I was an underdog, because I didn’t want to be in school, and it always had this quality of an uprising. When you first start out, you want people to know you. There is a quality of the unknown that is very sexy—like thinking, There might be a girl in this crowd who will have a conversation with me because she knows my music. For me, it has never been about fucking lots of girls. I could have fucked a lot more girls in my life if I hadn’t been trying so hard to get them to like me. If I have a conversation with a really hot girl that lasts all night and she says, “Wow, I had no idea I was going to like you this much,” that is the equivalent, for me, of getting laid.

Playboy: So how has that changed?

Mayer: I’m no longer playing music so I can walk into a party and talk to chicks, because people know who I am now. In fact, now I have a sort of negative connotation with that. [laughs] It’s a headache, you know?

Playboy: Meeting girls is a headache? You have to explain that.

Mayer: I hate being the heartbreaker. Hate it. If I date somebody and it doesn’t work out, it’s another nightmare for me. I don’t like the way the odds are stacked. If I date nine more girls before I get married—which I think would be completely appropriate—that would be nine more spats of character assassination. I don’t equate sex with release, I equate it with tension. It’s given me a lot of pause. Somewhere in my brain it has probably really f**ked me up.

Playboy: But who cares if people assassinate your character?

Mayer: I do. I just do. I consider myself a good guy, with the best of intentions. Anybody who has been in a relationship with me would stand by the fact that I’ve never been callous. I’ve never been a bad boy. I may have taken someone through the wringer psychologically, but I’ve never been sinister.

Playboy: So you’ve lost the motivation of playing music to meet girls.

Mayer: If I was playing it so I could meet hot chicks, I’ve met hot chicks, quote unquote. If I was playing it to make a ton of money, I’ve made a ton of money. If I was playing it to be well-known, I am well-known. Once you put aside girls and money, it forces you to realign your motivation for being a musician. Now I’m not a have-not but a have. Which is interesting, because music has to come from a have-not sort of place. And there are many places where I have-not.

Playboy: What motivates you now?

Mayer: My motivation is to prove people wrong, to confuse them. I enjoy the challenge—I must be addicted to the challenge. I’ve gone from being a musician to being a celebrity. And when people do that, their work usually suffers. There are tunes on Battle Studies that are more applicable to other people’s lives than anything I’ve ever written before. This whole time I’ve stayed vulnerable, stayed frustrated, stayed confused. This record is the trade-off to having sort of brutalized myself for a few years. So if people see that over the past couple of years I actually got a firmer grip on writing songs about the ups and downs of life, they might go, “How did he have the time to make a record? Was he writing ‘War of My Life’ in the middle of me thinking he was a douche bag? Did I ever actually know him? Maybe he’s a pretty solid guy.”

Playboy: What if you were to google the phrase John Mayer is a douche bag?

Mayer: You’d get a lot of hits. It’s this whole perception thing about tabloids, where 85 percent of the stories are not true. If you align yourself to be exactly who you know you are and to have dignity, maybe through that distorted lens you look askew to everyone else. I’ve done away with feeling aloof and trying to seem suave and bulletproof. I’ve resigned myself to being slightly awkward and goofballish.

Playboy: It seems as though you realize that celebrities who complain don’t generate much sympathy.

Mayer: I have never once said “I wish the press would leave me alone.” With Twitter, I can show my real voice. Here’s me thinking about stuff: “Wouldn’t it be cool if you could download food?” It has been important for me to keep communicating, even when magazines were calling me a rat and saying I was writing a book.

Playboy: Who did that?

Mayer:Star magazine at one point said I was writing a tell-all book for $10 million. On Star’s cover it said “What A Rat!” My entire life I’ve tried to be a nice guy. The best I ever felt was when friends’ parents would say, “John can come over any time. We love that kid.” When I date a girl and find out her friends approve of me, I love it. I love being liked! I’ve given microscopic dedication to doing the right thing, taking the high road, and all of a sudden Star magazine says, “He’s a rat.” I can’t tell you it didn’t give me that much more bloodlust to do what people thought I couldn’t do.