Singer-songwriter and guitar virtuoso John Mayer had a song on his major label debut record, Room For Squares, that foreshadowed a trend in his personal life. The blunt tune, “My Stupid Mouth,” recounts a very awkward date. “My stupid mouth / Has got me in trouble / I said too much again / To a date over dinner yesterday,” Mayer croons. “And I could see / She was offended / She said, ‘Well, anyway…’ / Just dying for a subject change.” The song continues to explain his penchant for putting his foot in his mouth, leading to the concluding promise, “I’m never speaking up again starting now.”
The multi-Grammy winner’s ex-girlfriends, including but not limited to the likes of Jessica Simpson, Katy Perry, Taylor Swift, and Jennifer Aniston, probably wish he’d kept the promise he made to the world in 2001 — but a quick Google search reveals that he definitely didn’t. However, Mayer also happens to be one of the best guitarists of his generation, who can also write a pop ballad on demand whenever he feels like it, so it’s no surprise that he’s continued to have professional success, even as he’s spewed TMI about his personal life all over the press.
But even Mayer’s most loyal fans — and Hollywood, for that matter — have their limits. It’s probably partially why 2017’s The Search for Everything is his most forgettable album to date, no matter its quality. Let’s consider some of the real reasons fans turned on John Mayer.
John Mayer publicly compared Jessica Simpson to drugs
Yup, you’ve read the heading correctly. John Mayer and pop singer-turned-fashion mogul Jessica Simpson dated for about two years in the mid-2000s, but in 2010, Mayer revealed intimate details about their sex life in a scandalous Playboy interview. He infamously called Simpson “sexual napalm,” but unfortunately didn’t stop there. Comparing her to a drug, he said, “Yeah, that girl is like crack cocaine to me. Sexually it was crazy.” Yikes.
For her part, Simpson was understandably hurt and “felt betrayed” by her ex’s very public comments. Admitting to Oprah Winfrey that she couldn’t bring herself to read the article, she said, “I was so disappointed in him … It made me so sad, and it was really discouraging, because that’s not the John that I knew.” While Mayer apologized (presumably via email), Simpson added, “I don’t accept it … I’m just gonna let that go. That part of my life is over.”
It wasn’t until her 2020 memoir, Open Book, that Simpson actually revealed how unhealthy her relationship with Mayer was. Per The New York Times, she wrote that she began to rely on alcohol to calm her insecurities surrounding Mayer, for whom she never felt smart enough, but noted that the Playboy interview “made it easy for [her] to walk away.” When asked about how Mayer might respond to the book, Simpson told The New York Times, “I don’t care.” We don’t blame you, Jessica.
John Mayer made inappropriate comments about race
Unfortunately, John Mayer’s extreme public comments don’t stop with past loves. The “Gravity” artist faced swift backlash for making racist comments in that same infamous Playboy interview.
In addition to comparing his genitals to a “white supremacist” while discussing his dating history, he claimed, “[Being Black is] making the most of your life, not taking a single moment for granted. Taking something that’s seen as a struggle and making it work for you, or you’ll die inside. Not to say that my struggle is like the collective struggle of Black America. But maybe my struggle is similar to one Black dude’s.” Um, okay. Mayer also used the N-word when talking about being accepted among the Black community. In response, rapper-actor Ice-T tweeted (via The Guardian), “Wow! That’s sad because I liked that dude … Well there go all his black fans and his hood pass … Damn John!!”
Mayer quickly apologized to fans on Twitter (via ABC News). “I am sorry that I used the word,” he wrote. “And it’s such a shame that I did because the point I was trying to make was in the exact opposite spirit of the word itself. It was arrogant of me to think I could intellectualize using it because I realize that there’s no intellectualizing a word that is so emotionally charged.” We certainly hope he learned something about white privilege from this experience.
John Mayer also used a homophobic slur
Unfortunately, John Mayer never stopped putting his foot in his mouth during that fateful 2010 Playboy interview. It was largely overlooked at the time, but he also used a homophobic slur when describing an encounter with Perez Hilton, during which the guitarist kissed the gossip blogger as a “joke” on New Year’s Eve. “I remember seeing Perez Hilton flitting about this club and acting as though he had just invented homosexuality,” Mayer told the outlet of why he pulled the stunt. “All of a sudden I thought, I can outgay this guy right now. I grabbed him and gave him the dirtiest, tongue-iest kiss I have ever put on anybody — almost as if I hated f**s.”
Of course, nothing about that is funny, and GLAAD quickly called for an apology from the Grammy Award winner. “Just as Mayer indicated in his [Twitter] apology, that he meant no offense in his use of the racist slur, we hope the intent behind his use of the F-word was not malicious,” the organization stated in part in a blog post. “As a public figure with millions of fans, Mayer should be more cognizant of the impact his casual use of both slurs can have.”
We unfortunately couldn’t find any evidence of Mayer apologizing for using the F-word.
Did John Mayer dare to break Taylor Swift's heart?
It’s hard to pin down the exact timeline of John Mayer and Taylor Swift’s short-lived relationship, but it happened somewhere between late 2009 and early 2010. But Swift doesn’t speak much about her romantic relationships to the press — she saves the kissing and telling for her songs, yet never explicitly confirms who they are about. In fact, the closest she’s come to naming names is the 2010 Speak Now track, “Dear John.”
The world has assumed that lyrics like, “Dear John, I see it all now that you’re gone / Don’t you think I was too young to be messed with? / The girl in the dress cried the whole way home / I shoulda known,” are about Mayer. … And so did he. “I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down,” Mayer told Rolling Stone in 2012. “I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”
While Swift has since refused to confirm the song’s subject, she did tell Glamour that Mayer was “presumptuous” for thinking he’d inspired it. Meanwhile, Mayer took it upon himself to write an assumed response in the form of his song, “Paper Doll,” which references “Dear John” and the dresses Swift has worn. It’s sad that the “Half of My Heart” collaborators were both left hurting over this breakup, but we do love the songs that came from that heartbreak.
John Mayer bragged about breaking up with everyone's best friend
John Mayer and Friends star Jennifer Aniston dated on and off between 2008 and 2009. And, true to form, he’s made some very public comments about their breakup. The first was outside of a gym, as E! News reported, when the musician said, “I’m the a**hole. I burned the American flag. I basically murdered an ideal.”
We have questions about why he’d brag about that, but Aniston went on to defend Mayer during an interview with Vogue in 2008. “He had to put that out there that he broke up with me. And especially because it’s me. It’s not just some girl he’s dating. I get it. We’re human,” she said. “But I feel seriously protective of him and us. Trust me, you’ll never see that happen again from that man.”
Mayer definitely proved Aniston’s prediction wrong in his 2010 Playboy interview. While he at least cleared the (low) bar of not talking about their sex life, he did basically diss her for aging: “I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction. And I always said, ‘These are the new rules.'” He admitted that he’d “always” love Aniston. How sweet … until it’s not: “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32.” Ouch!
John Mayer once appeared to be very full of himself
John Mayer is obviously an extremely talented musician, and you’d be hard-pressed to find a fellow guitarist or singer-songwriter who would deny that fact. Even Eric Clapton once called Mayer a “master” guitarist, saying, “He’s extremely gifted. His facility is phenomenal.” But did the constant praise go to the “Waiting on the World to change” hitmaker’s head? It certainly seemed that way during his notorious 2010 interviews with Rolling Stone and Playboy.
Mayer has often said he wants to settle down with someone, but has also made some mind-boggling comments about his criteria for planting real roots with a significant other. “Do you think it’s going to take meeting someone who I admire more than I admire myself?” he mused to Rolling Stone. We won’t deny that Mayer’s honest, but he has also had a hard time admitting that he needs to dial it all back sometimes. “I come on very strong. I am a very … I’m just very. V-E-R-Y. And if you can’t handle very, then I’m a d**che bag,” Mayer told Playboy. “But I think the world needs a little very.”
Judging from the swift backlash reaction to both of these interviews, the world essentially said, “Thanks, but no thanks, John.” Even Mayer would later admit that he was a “recovered ego addict” to MSNBC in 2015. Perhaps that’s why Forbes once attempted to answer the question: “Why John Mayer Is Music’s Forgotten Superstar.”
John Mayer: the king of TMI
Amid John Mayer’s disastrous interviews in 2010, there were also some pulled quotes that were just, well, gross. No one really needed to know about his bathroom habits, for example, but the “Who Says” singer shared his preferences with Rolling Stone. “I’ve got to go to the stall,” he said. “I can’t get a good flow going when I’m out in the world. But then, of course, you run the risk of people thinking you s**t all the time.”
Unfortunately, that was just the beginning of the things we all wished we didn’t know about Mayer … because he also spoke at length about self-pleasure at the time. “I am the new generation of masturbator… I’ve seen it all,” he told Rolling Stone. “Before I make coffee, I’ve seen more butt holes than a proctologist does in a week.” Apologies, readers — we wish we could unsee that quote, too. Mayer also admitted to Playboy that he, um, fantasizes about his exes: “Rather than meet somebody new, I would rather go home and replay the amazing experiences I’ve already had.”
It should go without saying that sex and sexuality are nothing to be ashamed of, but some details should probably be kept private — especially when most of your exes are famous, too.
John Mayer has objectified women
John Mayer has made millions of dollars off of love songs like “Your Body is a Wonderland” and “Daughters.” We’d hope that deep down, he’s a guy that cares about women as much as those songs portray. Unfortunately, on top of the cringe-worthy, TMI comments he’s made about his famous exes and private bedroom habits, some of the more general remarks he made about women during his 2010 Rolling Stone interview were equally head-scratch-worthy, making it seem as though he was more interested in objectifying women than connecting with the opposite sex on an emotional level.
“But isn’t it also about a beautiful vagina?” Mayer said, about his criteria for a life partner. “Like, you need to have them be able to go toe-to-toe with you intellectually. But don’t they also have to have a vagina you could pitch a tent on and just camp out on for, like, a weekend? Doesn’t that have to be there, too? The Joshua Tree of vaginas?” So much yikes.
John Mayer rehabbed his image and shared his ultimate dream
2010 was a rough year for John Mayer where media coverage is concerned, and he knows it. The backlash from the press and public led him to retreat to Montana, away from the bright lights of Hollywood, and write two albums — 2012’s Born and Raised and 2013’s Paradise Valley. “It’s rivers and cows,” he later told The New York Times. “There’s no sexuality there.” By 2017’s The Search for Everything, Mayer was ready to sing about romance again, saying, “I want to make music and be thought of as attractive. I was finally ready to re-enter that world and grow back into it.”
In his quieter years, Mayer famously dated pop star Katy Perry — the two ended things after a couple years in 2014 — and also did a lot of self-reflection. “I was just a jerk,” he previously admitted to CBS News of his 2010 word vomit in the press. “And it’s hard for people to process that.” Mayer added to The New York Times, “What has to happen for a guy to believe that he’s totally well-adjusted and be that far out of touch? My GPS was shattered, just shattered.”
So, if fans turned their back on Mayer, he seems to get it. But these days, he’s less about the notoriety and all about the music and settling down, hoping to one day have “the baby with the protective earphones” watching from the side of the stage during shows. We want that for you, too, John.
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