There are guys, there are guy's guys, and there are girl's guys. There are guys you like because they remind you of someone you know and there are guys that you hate because they remind you of someone you know. There are guys that you don't like but would love if they were your friends. And there are guys that you think are pretty cool but realize you'd totally get sick of if they were your friends. Somehow, John Mayer fits in all of these categories.
He's been called a douchebag, a gold digger, a lothario, and a charlatan*. But isn't John Mayer just kind of a regular dude? I had the (what's the opposite of) pleasure of attending a Mayer concert a few years back and all I can say was that it is not my kind of music. I did, though, laugh at one of the jokes he made between songs (he used the word "boner," 'nuff said), but the ladies were totally enthralled by him. Sure, most of the women were south of 23 and totally in the sweet spot for sensitive singer-songwriters. Many would likely have been equally rapt had they been sitting on the floor of a dorm room, listening to a shirtless trustafarian try to literally charm their pants off with a 2-chord song into which he incorporated their name.
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Somehow, John Mayer was able to make songs about being nice to girls (seriously, why the hell else can a track like "Daughters" possibly exist?) into a full-time job with a cult-ish following. But even that racket started growing stale. Sure he could sleep with college students and bachelorette parties who didn't care that his music sounded like a Dave Matthews Band rip-off. But where was the challenge? He needed an Everest (or to catch a marlin, whichever cliche you prefer), as any guy would.
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So, he started hunting bigger game: starlets. Word on the street has it that he got with Jennifer Love Hewitt back in the day but really hit the big time with Jessica Simpson. Suddenly, he wasn't just a guy that you could easily confuse with Jack Johnson any more. You really had to work at it to confuse him with Jack Johnson now. One day John Mayer is making a living by doing fun love songs and then, blau!, he's dating Jessica Simpson (that's 2/3 of the way to Britney Spears). He's talking to paparazzi, dropping cute phrases in Japanese (evidently he learned it in high school) about Jessica to interviewers, and generally loving life.
Of course, it didn't last (though word on the street is that Papa Joe liked normal guy Mayer more than pretty boy Nick Lachey). But it was a gateway to bigger things—he was on the list now. Along the way he picked up a bunch of extra tattoos because he would never need a regular job again (a dream of mine).