Issue 20: John Mayer Couldn’t Shut Up

Too many yikes to contain in the interview that almost killed this chump's career

(Content warning: This article discusses topics of racism, sexism, and homophobia. Seriously, this dude sucks.)

When the infamous Playboy interview with John Mayer went viral, I had never heard any of his music. He was largely famous in America and his brand of blues-inspired acoustic rock hadn't broken through into the British music mainstream. So, I knew him exclusively as a guy with a guitar who dated famous women. He was one of Jessica Simpson's first major boyfriends after her split from Nick Lachey. He had romanced Jennifer Aniston and Katy Perry and Taylor Swift. Before Pete Davidson, it felt like every female celebrity was obliged to date John Mayer for a few months, the celebrity equivalent of jury duty.

Being known as a womanizer is usually a good thing for famous dudes, or at least it was long viewed as a net-positive for their brand. In 2010, it was certainly seen as aspirational. Leonardo DiCaprio’s steady string of young hot models wasn’t viewed as creepy, mostly because he wasn’t pushing 50 and his pattern of only dating women under 25 wasn’t a sharable graph of provable data. George Clooney was still a dapper playboy who had yet to meet Amal. It made sense for Mayer, a sensitive curly-haired man who wrote songs like “Your Body is a Wonderland” to have this image as a pleaser of women. That went out the window the moment his most notorious interview went live. I remember the fallout far more vividly than any of his songs.

Playboy. "The Playboy Interview With John Mayer." March 2010. Rob Tannenbaum.

Image via Playboy.com.

(Read the profile here.)

By 2010, Mayer had released four albums, won seven Grammy Awards, and had a number-one hit atop the Billboard 200. He was both a critics’ darling and a commercial safe bet. But there were some bumps on the road. His 2009 album Battle Studies had received middling reviews and critics had started to find his lyricism more smarmy than charming. The New York Times said that the album highlights the extremely blatant chasm between John Mayer the musician and John Mayer the public character, a divide Mr. Mayer said he was eager to maintain." There was an unavoidable gap between the man who wrote sweet love songs and the perennial horndog with a string of famous women on his arm. Mayer would later admit that Battle Studies was not his best album and that he was playing it safe, a far cry from the days when Eric Clapton was heralding him as a bright new voice in the genre. It seemed as though he was becoming more known as a celebrity than a musician.

The infamous Playboy profile even opens with that acknowledgement: "Given the type of news coverage he gets, it may surprise you to learn that John Mayer is also a musician." Well, actually, it opens with an editor's note letting the reader know that the interview "contains language that may be offensive to some readers." Strap in, folks. Alongside his bona fide music creds, his romances are mentioned, because of course Playboy would be interested in that. In fairness, everyone was. It's a far cry from his youth when "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."

Mayer talks about his career in this piece but that’s not what we remember. That’s not what caused all the controversy. If Mayer had just been an arrogant jerk with a guitar, he would have been dragged on Twitter (where he was one of the site’s earliest examples of a perennially online celebrity whose quirky quips shtick grew thin really quickly.) But he wouldn’t have been seen as anything special. Oh, a musician’s an arsehole? Is water also wet? I’m not sure he even would have become notorious if he’d talked about his exes in a reasonably normal or charming way. But most of the truly notable playboys of our time – Jack Nicholson, Warren Beatty, Leonardo DiCaprio – don’t kiss and tell and it’s not hard to understand why.

As the writer of this piece notes, "he always brought up touchy subjects [...] 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." Well, "mischievous" is one word for it...

(Image via YouTube // Jimmy Kimmel Live!)

When asked why he's so anxious about never getting married, Mayer said, "What if I meet a woman and it’s love at first sight, and this woman has the greatest night of her life by telling me to fuck off because she knows my reputation?" This leads into him discussing a conversation about fame he had with Jennifer Aniston when they dated but before they'd gone public. She had warned him that press interest in him would drastically increase once his status as her boyfriend became known. And it did. Post-Pitt, Aniston's love life and status as the sad dumped wife was front page news for over a decade (and she had to call it out multiple times as creepy and sexist.)

Aniston is the ex that Mayer seems the most gentlemanly about, but that’s a very low bar and it still comes after his infamous public statement on their split which made him seem like a real piece of work. He mentioned the "regard for each other’s feelings that is pretty intense" between them and didn't reveal anything more revealing than that she's not one for modern technology ("If Jennifer Aniston knows how to use BitTorrent I’ll eat my f*cking shoe. One of the most significant differences between us was that I was tweeting.")

The interviewer asks Mayer, "If you didn’t know you, would you think you’re a douche bag?" He responds by noting that he's "very I’m just very. V-E-R-Y", which is why "black people love me." THEN he says, "Someone asked me the other day, “What does it feel like now to have a hood pass?” And by the way, it’s sort of a contradiction in terms, because if you really had a hood pass, you could call it a..." Do you need me to type here what he said next? Yup, the N-word. He says the N-word. Like, hard-N N-word. The journalist doesn't push back, or at least he doesn't on the page as it was presented to audiences. I imagine he knew that it would make for one hell of a headline so he just moved on. Hmm...

Oh, and don't worry, it does get worse, somehow.

When asked by the white interviewer if “black women throw themselves” at him, Mayer says that his penis is "white supremacist. I’ve got a Benetton heart and a f*ckin’ David Duke c*ck." But don't worry, he still thinks Holly Robinson Peete is pretty and that "Kerry Washington would break your heart like a white girl."

I’m not even sure how to talk about this. What is there to say? John Mayer was super sexist and racist, and he said it all so casually while the journalist coaxed him to go further? In response to hearing the N-word, Rob Tannenbaum decided, “Should I ask him about having sex with Black women?” THEN when he compared his penis to a KKK leader, he thought, “Now’s the time to ask him which Black women he would date.” What did Peete and Washington have to do with any of this? Why drag them into it?

Reading this piece made me feel a lot of animosity towards both Mayer and Tannenbaum. Yeah, the latter is there to get a good article and I bet Playboy sold more than a few issues based on this nightmare interview, but surely he could have gotten the juicy quotes and maybe a few more by calling out Mayer’s bigotry. Usually with celebrity profiles like this, you know you’re dealing with a limited time frame, a pushy publicist, and an agreement that some topics are no-gos. When you’re there to write a puff piece, you don’t expect to embody your best Edward Murrow.

But here? The rules were clearly different, right? That this got to publication with the N-word stuff intact suggests there was no publicist doing clean-up and Mayer didn’t try to stop it getting to shelves. I wonder if, with this being Playboy, it was just assumed that being “no filter” and candid would be seen as positive or kind of cool. Mayer’s verbal vomit on Twitter had gone down well with audiences, and everyone already thought he was a douchebag, so how could he make it any worse? Spoiler: he made it worse.

He takes umbrage with being called a womanizer and man-whore, lamenting, "When women are whorish, they’re owning their sexuality. When men are whorish, they’re disgusting beasts. I think they’re paying us back for a double standard that’s lasted for a hundred years." A lot of his quotes do sound like those "progressive" dudes who think they're being allies by spouting regressive self-deprecation.

I think Mayer's trying to be self-deprecating a lot in this piece, actually, but hoo boy he can't pull it off. You can't sell yourself as in on your own joke when you refer to your ex Jessica Simpson as being "like crack cocaine to me [...] Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm." It doesn't work when you refer to gay men as "f*gs" and say that you tried to "outgay" Perez Hilton by kissing him on New Year's Eve (PLAYBOY: Would you kiss Harvey Levin? MAYER: I would rim him, probably. I can’t just repeat the kissing trick.)

The final line of the piece is Mayer saying, "In 2010 my goal is to get more mentions in Us Weekly than ever." And lo and behold, the finger on the cursed monkey's paw curled down. The fallout was swift and furious. How could it not be? Even if he hadn’t been so openly homophobic and used the N-word, just talking about women like that would have been enough to ensure his image would be forever dented. “Sexual napalm” entered the pop culture lexicon, even if nobody entirely knew what it meant. Does he think that napalm is a drug or something you can be addicted to? Was he trying to say that sex with Jessica Simpson was so fiery that it was like an incendiary weapon used by American troops in Vietnam? It’s just what every woman wants to hear, right?! And it wasn’t taken as a compliment for Simpson by the media, who wanted yet another narrative to shame her with after the mom jeans fiasco.

To make matters worse (somehow), another interview with Mayer dropped at around the same time, this one with Rolling Stone. While he didn’t claim to have white supremacist genitalia in that piece, he does talk about wanting to find "the Joshua Tree of vaginas." For a songwriter, his way with words is not great. Then again, I always found “Your Body is a Wonderland” to be extremely creepy.

(Just pure sexual kryptonite. Ick. Image via Rolling Stone.)

Shortly after these interviews, Mayer offered a long and awkward apology on stage at a concert in Nashville, which was caught on camera by a fan and put on YouTube. It’s both self-congratulatory and self-flagellating, a very Mayer-esque combination. Entertainment Weekly was mixed on whether or not it was earnest, writing, “he appears to be genuinely contrite, unless he has recently developed SAG-worthy acting skills that we are unaware of. Though fulfilling his final pledge—"I quit the media game. I'm out. I'm done. I just want to play my guitar"—seems as though it may require a complete personality transplant, rather than a short-term spasm of regret, no matter how heartfelt.”

This was also the same year that Mayer’s ex-girlfriend Taylor Swift released the song “Dear John”, so this was not a good time for this dude.

Mayer took an extended break from the spotlight following this, which coincided with a period of major throat and voice problems that required surgery and extensive vocal rest. He returned in 2012 with a new album and further contrition over his acute case of assholeism (but he also thought it was unfair how Swift had thrown him under the bus with that song.) Nowadays, Mayer is still releasing music and touring. He is also a regular member of Dead & Company, one of the groups made up of former Grateful Dead members who still attract loyal devotion from Deadheads. He collects watches, hosts a show on Sirius XM, and does some good charity work. He recently gained some real credit among nerds when he bought the Henson Studios lot, saving it from potentially being taken over and knocked down by Scientologists. I wish more rich people did stuff like that instead of collaborating with fascists.

Jessica Simpson opened up about her romance with Mayer in her memoir, Open Book. It doesn’t paint a positive picture of him, not that he needed any help on that front. Mayer allegedly broke up with Simpson nine times, and each time it was over email. Simpson claims that Mayer lambasted her drinking but rather than get her help for it, which she would in later years, he got her some Xanax. He seemed to believe he was so much smarter and more interesting than her, and treated her accordingly. Throw him into the sea, Jessica. Mayer has since apologized for his behaviour, but Simpson didn't want to accept it. Can you blame her?

Aside from being just the absolute worst, this profile really cemented for me how little patience we have for this strain of male celebrity in 2025. Tortured genius types are forever divisive and so are hound dogs but blending that together makes for an insufferable mix that not even the most charming and talented people can pull off. Trying to intellectualize your endless woman-chasing, or turning it into quips you think are witty but are just creepy and racist, is deeply ill-advised. Nobody likes a blabbermouth who loves the sound of his own voice. If you’re going to be a playboy, you have to also be a “gentleman”, at least publicly, and you have to make sure none of your exes talk about you to the press. There’s a reason that Leo is rumoured to make all of his girlfriends sign NDAs, and he’s savvy enough to keep his part of the bargain intact by not talking about his personal life in interviews.

It might also be because this sort of behaviour is now seen as actively predatory and/or part of a hard-right misogynistic agenda in the vein of Andrew Tate. It’s seen as desirable largely within a political context that’s intended to uphold toxic masculinity and the idea of women being chattel.

I wouldn’t say that John Mayer has redeemed himself, per se. He’s still a douche. He’s just a quieter one now, which is a smart move. To be more specific, I would say he’s a f*ckboi, which is the more petulant version of a dirtbag and with none of the pleasures a good self-respecting dirtbag can provide. Not being an endless tabloid staple does make it easier to be a manchild without stirring up any internet backlash. He’s still apparently a playboy. Last year, it was rumoured that he was dating Kiernan Shipka. Girl, run.

Thanks for reading. You can check out my work scattered across the internet. Over on Pajiba.com, I wrote about Diane Warren’s relentless domination of the Best Original Song Oscar and why she’s never won the main award. I also wrote about Amanda Palmer, and I think I cracked the code on why Americans have never embraced Robbie Williams. For Paste Books, I delved into the current reigning series of Booktok, the Empyrean saga.