The Top 5 Douchiest John Mayer Moments

There may be no greater pantomime villain in pop music than John Mayer. Nobody is doused with more haterade than this guy. And with good reason! Not content with being a undoubtedly gifted songwriter, singer and guitar player, Mayer has felt compelled to make himself into a bona fide public persona; a commentator on society and the human heart. How’s that working out for him? Well, lately… NOT SO WELL!

So, in honor of Mayer’s lengthy and instantly legendary Playboy interview (a piece, if I may steal someone’s tweet from yesterday, which marked possibly the first time people really did read Playboy just for the articles), we thought we’d assemble the five biggest faux pas in Mayer’s outspoken history. On whether it’s in interviews, on Twitter or on TMZ, John Mayer just can’t stop saying stupid s++t.

1. BAD OPENER: It’s one thing to be Trashy McTrashmouth when you talk to the tabloids or TMZ, but if you’ve got the opportunity to talk to the Grey Lady (or, formally, The New York Times), shouldn’t you open with a stronger opening salvo than, “I should be having sex with more girls“? In the words of MTV icon Ed Lover, “C’mon son.”

2. COUGAR PATROL: The whole, “this is not my mother, this is my date,” episode. A prank (hopefully) pulled off by the dinner-jacket-rocking duo of Mayer and Rob Dyrdek, involving being seen by TMZ cameras coming out of an L.A nightclub with two rather older women. You can’t really complain about all the attention when you so willingly engage in the game.

3.) DAS RACIST? Of the many, many, many not-so-bon-mots delivered in the Playboy piece, perhaps the most controversial were his musings on race. It perfectly illustrated how there’s no such thing as racism Lite. It was probably also the most epic example of a public figure wishing they had a rewind button. On the possibility of dating an African-American woman, Mayer had this to say: “I don’t think I open myself to it. My d**k is sort of like a white supremacist. I’ve got a Benetton heart and a f***in’ David Duke c**k. I’m going to start dating separately from my d**k.” And that, my friends, is how you become a trending topic.

4.) WAH! MY LOVE IS HEAVY AND IT HURTS RIGHT HERE: “This heart didn’t come with instructions.” Yeah, that’s some real poetry (albeit the kind that gets scribbled on the margins by disillusioned high school girls… the high school girls reading Buzzworthy excepted, of course). But in this case, context is king, and the context was Mayer publicly Tweeting about one of his multiple breakups with Jennifer Aniston. Grow some, dude! If I may paraphrase thewords of Will Ferrell as Ricky Bobby in Taladega Nights, you gotta “PUSH IT DOWN.”

5.) SEXUAL RECYCLING: From a Rolling Stone interview, earlier this year, Mayer on love, actually: “All I want to do is f**k girls I’ve already f**cked because I can’t fathom explaining myself to somebody who can’t believe I’d be interested in them.” Happy Valentine’s Day, lovers. Now let’s watch the “Daughters” video.