As John Mayer ambles over to his marijuana vaporizer – a small wooden device that emits a UFO-like blue glow in his darkened Pittsburgh hotel room – he shares a passing thought. "I bought myself a Playgirl once," he says, taking a robust, smokeless hit of weed from a plastic tube.
"I just loved the feeling that there was a porno you really, really weren't supposed to have," Mayer adds. He laughs as he sprawls his six-foot-three body onto a couch, his brown eyes unfocused. It's around midnight, less than twenty-four hours before the first show of his co-headlining tour with Sheryl Crow, and he's dressed like an NBA player on a day off, in a hoodie and long shorts that precisely match his limited-edition Nikes. "If there's some shit I'm not supposed to have that's on the top rack, with the black bar over the bag, I want to know what's in there. I don't care what it is – furniture, spider monkeys." He adds that thanks to his one-time perusal of nude-dude centerfolds, he's sure that he's not gay. "Which is different than might not be gay," he says. "Not to say I wouldn't enjoy the energy of watching a guy and a girl have sex. I think I'd vomit out of pure arousal. Have you ever seen a guy and girl have sex in person?"
John Mayer can't stop talking. He knows it, too – he even wrote a song about the problem, "My Stupid Mouth," from his first album. "I'm a liability to my art," Mayer says Big Mouth strikes again over brunch in New York at a Mexican restaurant, four days before that night in Pittsburgh. "I'm at a point right now where the more I talk, the more I'm going to say something in the next twelve months that's going to damage my career." (It turns out he does keep quiet about one thing: A week after our last conversation, Us Weekly reports that Mayer has just begun dating Jessica Simpson, whom he met at Clive Davis' Grammy party last year. "John is an incredibly talented artist," Simpson told the magazine, in a non-denial.) Though his baby face is as unlined as his shiny-new white Stussy T-shirt, Mayer, 28, is groggy after a night of barhopping – during which he jumped onstage and indulged in his new hobby of stand-up comedy.
Here is one of John Mayer's jokes: "Everyone thinks Brad Pitt has it great because he married Angelina Jolie. I think he has it terrible, because when Angelina Jolie is giving you a blow job, what do you tip your head back and think of to help you finish? You have nothing left – just Jesus on a polar bear in the middle of the snow, saying, 'You greedy motherfucker, I've got nothing for you.' "
And another: "I'm not worried about how small my penis is – I'm worried about how dark it is. I have a Dominican penis. My penis hit six home runs last year; my penis wears shoes without socks." Performing in June at the Comedy Cellar in New York, Mayer did a David Chappelle-esque routine that imagined white people being allowed to use the n word – a blogger reported, out of context, that Mayer had used the offending word, and a brief media furor ensued. So it's not surprising when Mayer says, "Everyone begs me not to do stand-up. Everyone connected to my well-being and on my payroll says stand-up is terrible. When I say, 'I'm doing stand-up tonight,' they hear, 'I'm going to start heroin.'" On some level, Mayer agrees – but he's also sick of being forced to apologize for his unguarded comments. He leans close to my digital recorder and says, "Everybody right now in the world of entertainment is a pussy. A pussy," he says, drawing out the last word. "They're all so sensitive. What the fuck happened?"
Some of Mayer's fans may be asking the same question about their favorite sleepy-eyed balladeer. In 2004 he won two Grammys with the sentimental acoustic tune "Daughters" – his biggest hit since 2001's "Your Body Is a Wonderland." He had begged his label and management not to release "Daughters" – the only acoustic tune on his second album, Heavier Things – as a single, fearing that it would cement his image as a teeny-bopper-pleasing softy. "I saw that as career death," he says. His manager, Michael McDonald (no, not the Doobie Brother), remembers a "battle" over the song. Mayer lost.
Since then, he has spent just about all of his time trying to move away from sensitive. "It was, 'let me take a year and get myself on track,'" he says. "I've met people who didn't realize they were off target, and they looked up and they were forty – they had six failed records, but everyone told them they were great. And they're fucking miserable." To avoid that fate, Mayer unleashed his formidable Stevie Ray Vaughn-inspired electric-guitar chops in jams with Buddy Guy, Herbie Hancock, B.B. King, Eric Clapton and Vaughn's old backing band, Double Trouble. He mocked his fans and himself in the unexpectedly hilarious VH1 comedy special John Mayer Has a TV Show – in which he informed a credulous group of teenage fans that all of his hits were ghostwritten by Richard Marx. And last year, he recorded a fiery blues-rock live album, Try!, with the John Mayer Trio, a group he formed with two of the industry's most elite session musicians, drummer Steve Jordan (who has played with Keith Richards and Bruce Springsteen) and bassist Pino Palladino (who was the Who's choice to replace John Entwistle). "John Mayer Trio is the anti-'Daughters,' the anti-'Wonderland,'" Mayer says. Along the way, Mayer – who had been until age twenty-six the least punk-rock straight-edge dude on Earth – also started drinking scotch and smoking (or rather, vaporizing) pot.
The result of all this change is Mayer's third studio album, Continuum – which has a funky, slow-grooving, soul-man feel, polished to a Steely Dan-worthy sheen. For all of its falsetto-laden soulfulness, there's no obvious follow-up to Mayer's twin smashes on Continuum, and the disc was enough of a departure to prompt Don lenner – the since-ousted head of Mayer's label, Columbia Records – to tell Mayer that he didn't hear a single. Mayer didn't take the news well. "I cried all day," he says in the Pittsburgh hotel room. "My chest was burning because it's like sending letters every day to someone you love, and you find out they threw 'em all out."
He contemplated quitting the music business. "I started looking up design schools online, because I was ready to go to design school," says Mayer, who attended Berklee College of Music for two semesters before dropping out in 1998. But that same day, Mayer was finishing a Curtis Mayfield-inspired tune called "Waiting on the World to Change," which ended up as the album's first single. "I knew it was a hit," he says. "And by the end of the day, I'd gone back to 'Nah, fuck that, this is a great record.' "
Still, Mayer's reaction to Ienner's snub was telling. His mother and father – a former teacher and a principal, respectively – were painfully unsupportive of his musical ambitions when he was a teenager. "Here's some psychobabble," Mayer says, sighing. "I'm out to impress the mom and dad, all the time." When he was young, Mayer loved being singled out as the only good kid in a group of malefactors: "Like, 'Everybody sucks! But not you, John' or 'Everybody sucks – why can't you be like John?' I'd like to be the 'Why can't you be like John?' of the music industry."
On a sunny Wednesday afternoon in an amphitheater in Burgettstown, Pennsylvania, Mayer stands alone onstage, looking out at 23,000 empty seats. Strapping on a Fender Strat, one of more than 200 guitars he owns, he begins his sound check by picking out an uncharacteristically sloppy version of the opening riff from Eric Clapton's "Layla." Discussing his role models at the New York brunch, Mayer says, "It's 'What would Springsteen do?' calculated to my age. And 'What would Clapton do?' Although the answer to that question is 'drugs' at my age. So maybe it's 'What would Clapton do at age sixty-one?' "
Mayer spent a week with Clapton at his estate in the English countryside, where the two wrote a bunch of songs together – which they have no plans yet to release. (Mayer has had similar songwriting sessions with his pal Alicia Keys.) After seeing the kind of cash Clapton throws at cars and vintage watches, Mayer raised the stakes on his own spending – even buying a $134,000 Porsche Turbo S sight unseen, after his mentor told him it was a mandatory rock-star move. "I literally called the Porsche dealer in New York City from Clapton's living room," he recalls. "This thing goes so fast, the front almost comes off the ground." Mayer ended up selling the car, though, after seeing the paraplegics in the documentary Murderball. "I went, 'You know what? I don't need another thing in my life that's gonna possibly take me out.'" Needless to say, Clapton's influence also extends to Mayer's music – the groovy Continuum track "I Don't Trust Myself With Loving You" sounds like the greatest Eighties-era E.C. tune never recorded, complete with an "It's in the Way That You Use It"-style intro. And the rest of Continuum is packed with slow-hand, virtuoso-at-rest guitar leads.
Onstage in Burgettstown, Mayer churns out funky blues riffs on guitar after guitar, all of them Strats – a white one, a black one and his weathered old SRV signature model, bought with money he earned working at a gas station as a teenager. At first it seems like he's just noodling, as if the amphitheater is a giant Guitar Center. But then he calls for his techs to switch out one particular amplifier in his rig, and it becomes clear that he's laboriously working out tones for his set list. "Does this sound spiky to you?" he asks his sound engineer, Chad Franscoviak, of one Strat – which to the uninitiated ear sounds about as good as the other eight guitars he's been playing.
The process takes hours. The sardonic, bespectacled Franscoviak – who is also Mayer's roommate at his house in Los Angeles, where the pair live a scaled-down version of the Entourage lifestyle – says that the scene is a typical example of Mayer's perfectionism. "I think having seen that provides you with a lot of insight into the process of making the [new] record," says Franscoviak. "John hears something in his head, and he won't rest until he achieves it." Mayer's drive extends even to his gaming: Franscoviak doesn't remember ever beating his roomie at their current fave, Rockstar Games' ultrarealistic Table Tennis. "Before that it was Halo, and no one could beat him," Franscoviak says. "That's pretty much his MO if he finds an interest in something – it doesn't matter how incidental it is." Mayer wants to be the best at everything, to have the best of everything – whether it's guitar tones, sneakers, cars, watches, twenty-five-year-old scotch or even sidemen.
Back in the hotel room – after some Glenfiddich, Caesar salad and vaporizing – Mayer and I are laughing about B.B. King's sex life. Mayer is serious enough about his blues scholarship to have read King's 1996 autobiography – though not serious enough to actually have finished it. "I got to, like, chapter three, and he'd bedded, like, 600 girls," he says, shaking his head. "It's like an erotic novel written from the point of view of an eighty-year-old: 'She was sweeter than molasses. I sampled her sweet molasses in January. We would go on up to the top of that maple tree....'"
Mayer's own sexual adventures are less exotic. Six years ago, on one of his first tours, he decided it would be "fun" to sleep with some fans. "I slept with, like, three girls in a week," he remembers. "I thought that's what you did, but there was one girl, I don't remember anything about her, but I left my own body and looked down at myself and said, 'Nuh-uh. Not you.' I stayed up all night and didn't sleep." He never had sex with a fan again – though that doesn't rule out voyeurism. "Totally different. There's ways to have fun with people without ever worrying about violating somebody."
Mayer has plenty of platonic female friends, but he finds himself seeing a lot less of them when they find boyfriends. "If your girlfriend knows me, she's really not allowed to see me," he says. "Guys assume that 'Wonderland' guy wants to take their girl." (Later that night, Mayer shares a list of rules on "How to be John Mayer's girlfriend." Jessica, you can clip this out: "One: You've got to be really careful with me on the phone. Distance makes the brain grow more maniacal. Two: Twenty-four-hour phone-sex assistance. If there's a cute girl in the front row, I'm gonna run offstage and call you. Three: You have to run every single fantasy you've ever had through me. You'll never cheat. You see a cute guy at the gym, I'll be him. Or we'll get him. I don't care.")
Mayer knows that he doesn't have the blues birthright of B.B. King or Buddy Guy. But he's had his version of hard times. When Mayer was seventeen years old, his heart started beating irregularly – an episode of arrhythmia that sent him to the hospital for a weekend. Until they found the right combination of medicines to fix the problem, his doctors were ready to stop his heart and restart it.
"It was so frightening at the time to be seventeen and have heart monitors hooked up to you," says Mayer. "That was the moment the songwriter in me was born. I discovered a whole other side of me. I came home that night and started writing lyrics. I discovered it all at once: It was like opening up a lockbox, and inside was a depth that I didn't even know I had as a person, or a writer – incredible creativity and vision and neurosis, complete neurosis. They all go together in a package." Afterward, Mayer started having crippling anxiety attacks, which he's only conquered in the past two years – to this day, he keeps a Xanax in the small pocket of his jeans at all times as an insurance measure.
Very little of this turmoil is evident in Mayer's music, which shuns noise and aggression. "It's not a part of my personality," he says. "I was a mild kid, man. I don't yell. There's some people who don't like me, just because I represent a certain kind of normalcy that people see as a waste of a music gig." He laughs, gets up to pour more water for his scotch and keeps talking. "I roll with the same truth as to who I am as the hardest-core punk rocker or the worthiest rapper," he says. "I am as John Mayer as 50 Cent is 50 Cent or Eminem is Eminem. And I think that's why I am where I am: Know who you are and be who you are. All the way. All the way to the hilt."