John Mayer’s soulful vocals and his salacious dating life have become the two biggest things about the singer-songwriter. Sometimes, his explosive bedroom life has even overshadowed his massive career, which is saying something. But then again, with infamous flings and at least one Taylor Swift revenge song, who can blame us? Here are facts about John Mayer, pop music’s bad boy.
1. That Guy Is Poison
At one point, John Mayer's reputation for being a serial stud was so bad, he had to deal with a brutal rejection. According to the pop star himself, he went up to a woman and gave her his number. Her response was soul-crushing. She apparently looked at it, looked at him, and told him: "I probably won’t use it". Ouch.
2. His Dear John Letter
For a guy with so many famous exes, it seems that Mayer would prefer to dump a famous song the most: his hit ditty "Your Body is a Wonderland". Mayer hates the song's legacy—especially since he gets constant ridicule about it. Apparently, inebriated men love to jeer the lyrics at him while he's walking down the street.
3. The Scent of a Woman
Mayer has one very strange and pretty disturbing talent: He can guess the perfume a woman is wearing. In a 2012 Rolling Stone interview, a group of girls passed him by, and Mayer bragged to the journalist that he was good with scents. He then turned to the women and asked if one of them was wearing a perfume called "Child". A blonde replied, "I am. Well done".
4. Performance Issues
The line, "She’ll fight for you like [heck]/ Then force herself to like some other man" is from Mayer’s song "Never on the Day You Leave". It has an absolutely heartbreaking history. Mayer wrote the song after a breakup with an unidentified ex, and he says that this line in particular is so painful, he couldn’t even perform the song live and cried multiple times while recording it.
5. The Aphrodisia of Syntax
Mayer admits that he has a thing for good grammar. As he said, the truest way to his heart is "good spelling and good grammar, good punctuation, capitalize only where you are supposed to capitalize, it's done". But as we'll see when it came to his infamous relationship with Jessica Simpson, this attraction took on a bizarre but major dark side.
6. Mars Attacks
Starting from when he was a boy, Mayer suffered from crippling panic attacks. When he got famous, they only got worse. He was overly anxious to get praise for his musicianship and songwriting abilities, and he feared that his fame would flame out. Any comments about his performances or his so-called womanizing intensified his anxiety.
7. Pump the Brakes
Mayer admitted in a 2012 Rolling Stone interview that his panic breakdowns got so severe, he feared having to check himself into a mental institution. Mayer’s friend Joe Beleznay confirmed the extent of Mayer’s panic, and Beleznay says Mayer’s mind "works at such speed" that he would "second-guess his sanity at times".
8. Meet the Parents
John Clayton Mayer was born in Bridgeport, Connecticut in 1977 to Margaret and Richard Mayer, a middle school teacher and a high school principal, respectively. His parents are 19 years apart in age, and Mayer has revealed that they fought a lot at home, forcing him to "disappear and create my own world I could believe in".
9. Babymaking Music
Mayer has confessed that in the early days of his fame, he used his music to get women into bed with him—but it gets even creepier. Though he says he doesn't play his music while he's doing the deed, he has admitted that some girls have "asked me to sing…in the run-up to it". Now that's an image I want to get out of my head.
10. Don't Take It to Bed
Mayer apparently suffers from horrible nightmares—with a bizarre twist. In them, Mayer dreams he's about to get it on with someone, only to have the paparazzi burst in and make him unable to perform.
11. Battle of the Balladeers
When Mayer dated reigning pop princess Taylor Swift, he finally met his match. Although Swift never confirms who her songs are about, it's pretty easy to see that her scathing number "Dear John" is about Mayer. Mayer's response to the song was incredibly bitter. He said it "humiliated" him and chided that it was "a really lousy thing for her to do".
12. The One Who Got Away
Mayer felt lambasted by Taylor Swift, but it didn’t stop him from getting seriously involved with pop songstress Katy Perry. The two dated on and off between 2012 and 2014. They never confirmed an engagement between them, but Perry did sport three different diamond bands on her ring finger when they were "on," so make of that what you will.
13. Mayer Admiration Society
Perry was apparently a huge Mayer fan before they got together. She called him incredibly talented, gifted, and a "genius songwriter". She also said it was "natural" that they’d end up working together. The duo released a ballad in August 2013 called "Who You Love," and they sure made a beautiful couple in the video.
14. Ex Marks the Spot
Mayer’s 2017 song "Still Feel Like Your Man" is about Perry. Apparently, by 2018 he hadn't dated anyone since they were together; as he said, "Who else would I be thinking about?" His lyrics prove he loved her. As he wrote, "I still keep your shampoo in my shower, in case you wanna wash your hair / You probably found yourself someone / I do not really care".
15. A Blue Ribbon in Bed
Katy Perry appeared on James Corden’s The Late Late Show in June 2017. While there, she made a scandalous revelation. On one of Corden's games, the host asked her to rank three of her celebrity ex's: Diplo, Orlando Bloom, and John Mayer. Perry dished out loud that Mayer was the best in bed. To make it extra awkward, Bloom and Perry have since gotten back together.
16. The Name Game
Perry also gave Mayer a tribute in one of her album titles. Apparently, Mayer used to call her "Prism," which is the same name as her 2013 album.
17. Wonder Woman’s Identity
Mayer's song "Your Body is a Wonderland" was an absolute smash hit, and people have theorized for years about who Mayer wrote it about. Sleuthing fans believe they have an answer. Around the time he wrote it, Mayer was dating Jennifer Love Hewitt. Many still believe the song is about her, but Love Hewitt denied it in 2018...and Mayer has revealed the real inspiration.
18. Mystery Solved
In a 2012 interview, Mayer admitted that "Your Body is a Wonderland" is actually about a girl he fell in love with when he was only 14 years old. He still hasn't revealed her identity, but he said of her, "This woman is precious. She can vouch for me not as a celebrity. She carries with her information of this 14-year-old boy she knew".
19. Little Bird Should Stop Chirping
Another one of Mayer's most famous exes was sitcom darling Jennifer Aniston, whom he dated from 2008 to 2009. Although their breakup seemed amicable at the time, Mayer kissed and told in the worst way possible. The couple had a big age gap, and according to Mayer, the older Aniston thought that he spent too much time on the internet.
As Mayer rather unkindly said, "The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998".
20. Why Me?
Mayer was also infamously loud and proud about the fact that he was the one who dumped Aniston. As Aniston later put it, "He had to put that out there that he broke up with me," she said regretfully, "And especially because it’s me. It’s not just some girl he’s dating". Aniston's friend Andy Cohen once said she still hasn't forgiven him.
21. Finding Tune in Trauma
At the age of 17, Mayer got a terrifying diagnosis that led to his musical awakening. The doctors told him he had a sudden and acute onset of cardiac arrhythmia. He had to spend the weekend in the hospital, and the trauma of the incident was his creative impetus to write his first song lyrics after he got home.
22. Hit Them With a Hospital Selfie
In December 2017, Mayer got into medical trouble again and rushed to the hospital for an emergency appendectomy. A newly self-deprecating Mayer then posted a selfie online for his legions of fans wishing him a speedy recovery. In it, a scruffy-looking Mayer appears in a hospital gown with a joking caption, "Still got it".
23. Tough Crowd
Trending comedian Kumail Nanjiani has a pretty incriminating story about Mayer. The singer apparently fancies himself as a standup comedian, and he once prevented Nanijani from going onstage just so he could do a quick 5-minute stint for the audience. Well, 5 minutes turned to 20 minutes, and Mayer simply refused to leave. And then it got even worse.
24. He's Got the Jokes
When Nanjiani finally got on stage to perform his set like he was supposed to, Mayer returned the favor by heckling him. He reportedly called Nanjiana "Kabul" and said that "he looked like a brown guy but sounded like a white guy". Oh, John.
25. Meet Your Heroes
Growing up, Mayer idolized rock and roll greats like Eric Clapton and Stevie Ray Vaughan.
26. Control Yourself
Mayer has been honest about his struggles with booze and finding emotional stability. Though he never had a serious problem, he does say that he never felt like he could drink the right amount, and never believed he was "succeeding at life" when he drank. These days, he's stopped drinking almost entirely, and calls it a "con".
27. An Old Lover
In a recent interview, Mayer admitted that he really likes his ex Taylor Swift's song "Lover," but he does have one problem with it. His beef has to do with the lyric about keeping "the Christmas lights up ‘til January". As Mayer says, that's "insane" because "Everyone keeps their Christmas lights up until January". Look, people, he's right.
28. Mega Mentor
Not everyone can say they have a bona fide rock god as a mentor, but in John Mayer's case, it's true. Music icon Eric Clapton took an interest in Mayer's talent, and even invited him to a 10-day writing workshop in 2006 at the beginning of his career. According to Clapton himself, he spent most of his time trying to get Mayer out of the habit of being a "bedroom guitar player".
Despite being Mayer's mentor, Clapton isn't afraid to give his pupil some tough love. Although the seasoned guitarist admits Mayer's immense talent, he also publicly called Mayer out in an interview for being "a prime saboteur" of himself. Yep, that sounds about right to me.
30. His Own Worst Enemy
It's not like Mayer doesn't have a sense of humor about his bad boy reputation. Once, a fan commented on one of his Instagram posts, "You're so beautiful! How are you still single?" Mayer had the perfect response. His reply? "Google me".
31. Diss and Tell
Mayer credits one Hollywood party and one mega star with the realization that he should probably cool it on the dating front. Apparently in 2016, Mayer attended an Oscar party with the hopes of getting lucky. But when he looked over and saw Scarlett Johansson, all he could think was "She wants nothing to do with you". After that, Mayer left her alone.
32. Batting 500
In one recent interview, Mayer finally revealed his "number"—that is, how many women he's slept with. While his interviewer guessed that the number had to be over 800 women, Mayer finally admitted it was a "soft 500". He griped at them, "Are you guys surprised that I have slept with less than 800 people?!" Um, is 500 much better?
33. Six Is the New Soft 500
In typical Mayer fashion, he later back-tracked big time on his claim that he'd bedded 500 women. After word got out about his astronomical number, Mayer released a statement saying he'd revisited his dating history, and the true number was actually: six. Wow, I'm bad at counting too, but I think John needs to get a doctor to check him out.
34. Grab Your Calculators
If Mayer counts six ex-lovers, that’s new math and we’re not getting it. Besides songstresses Taylor Swift, Katy Perry, and Jessica Simpson, Mayer’s other reported exes include Renee Zellweger, Kim Kardashian, Minka Kelly, Mandy Moore, Cameron Diaz, and Rashida Jones. It's like a little black book all in itself.
35. My Best Work
Mayer's third album Continuum, which he released in 2006, is widely considered his best work. In fact, even Mayer admits this. When someone asked him what his best album was, Mayer replied with stereotypical honesty: "I know that I’m supposed to say that my newest is the best one. [But] Continuum is my best one".
36. Good Company
In 2015, Mayer's career took a turn no one could have predicted. He started touring with members of the iconic jam band the Grateful Dead. Together, Mayer and the legends formed Dead & Company, and Mayer is apparently egoless about sharing the stage.
37. In Poop We Trust
The crooner is infamous on Twitter for his twisted sense of humor, particularly his commitment to making poop jokes. Believe it or not, his salt-of-the-Earth musings have earned him a massive online following. One example? He once tweeted, "I thought I had to [toot] but it turned out it was just a poop". Now, that is kind of funny.
38. Playing Dress-up
Surprisingly to some, Mayer is a bit of a fashionista. In 2012, he admitted that he spent over $200,000 on clothes in the last year alone.
39. John of All Trades
Mayer can be downright obsessive about the hobbies he gets into. For example, he once tracked down a rare Rolex watch face, which people actually now officially call the "Mayer dial". Even weirder, he enlisted magician David Blaine to teach him how to hold his breath for a prolonged period of time; Mayer made it to an impressive four minutes, 17 seconds.
40. Working With Clay
When he was young, Mayer got into the prestigious Berklee College of Music. While there, he quickly hooked up another young musician, Clay Cook, and the duo started jamming together. Mayer was so impressed, he ditched Berklee and took off to Atlanta to perform alongside Cook in a band. But trouble was on the horizon.
41. Too Many Cooks in the Kitchen
Mayer and Cook soon clashed with each other over musical styles and creative directions, and they eventually had a falling out that was so bitter, they stopped working together entirely. Cook didn’t fall by the wayside, though—he’s now a member of the hugely successful country music group the Zac Brown Band, and he and Mayer have since patched things up.
42. Mirror, Mirror on the Musical Wall
Something special happened in Toronto in April 2017. Current pop sensation Shawn Mendes was in his hometown, attending a Mayer concert, and the two ended up performing a mash-up of their hits onstage. Photos of them that night are striking. They look related, wearing nearly identical outfits and playing similar acoustic guitars.
43. Make Like a Tree and Get out of Here
Mayer got musical inspiration as a child from a very unlikely source: the 1980s film classic Back to the Future. He was so enthralled by the film's guitar-playing scene in the high school gym that he decided he wanted to be just like Michael J. Fox's Marty McFly and shred it on guitar too. Looks like that worked out for him.
44. Don't Mess With Jess
Of all his ill-fated romances, John Mayer's relationship with pop star Jessica Simpson has gone down in infamy. For seemingly ages, the pair were on- and off-again, and Simpson’s memoir Open Book reveals the absolutely heartbreaking ordeals Mayer forced her through. According to her, it was always Mayer breaking up with her and then taking her back, and they broke up something like nine times throughout their steamy relationship.
As she wrote, "I always saw it as him mercilessly taking me in from the cold". Sadly, that was just the beginning of the nightmare.
45. The Right Words
Simpson confessed that while she was dating Mayer, she was so insecure about herself that she would spend hours upon hours agonizing over the texts she’d send him, making sure every word was perfect and all the grammar in place. After all, he liked a girl who could write properly. In the end, it was never enough.
46. Portrait of a Lady
According to Simpson, Mayer was "obsessed" with her, but this obsession had a chilling dark side. Mayer would apparently study her entire body and take photos of her constantly, so much so that Simpson confessed she "worried he was keeping souvenirs before dumping me again". All I can say is…run away, Jess.
47. The Romo Rebound
During one of her more prolonged off periods with Mayer, Simpson started dating Dallas Cowboys quarterback Tony Romo, and it seemed like she had finally shaken Mayer off for good. The stable, healthy relationship lasted a whole two years—right up until Mayer busted back into her life and royally messed it up all over again.
48. Big Mistake, Huge
Simpson swore she would tell Romo about every bit of contact she had with Mayer, but one day the singer came to a family event, declared his love for her in front of everyone, and begged her to take him back. But wait, there’s more. Though Simpson managed to say "no thanks," she also didn’t tell Tony about it. This was a bad move.
When Romo found out, he dumped her…and she went right back to Mayer. This was never going to end well—but their final breakup took "notorious" to the next level.
49. The Words Heard Round the World
In 2010, Mayer gave a now-infamous interview with Playboy where he kissed and told. Uh, big time. In the article, he claimed he was addicted to Simpson and waxed poetic about their private bedroom life, calling her "[sensual] napalm" for the entire world to hear (and remember forever). Simpson’s response was swift and brutal.
After the interview, Simpson cut off all contact. "When he reached out to me, I changed my number and changed my email," she wrote in her memoir. "Delete".
50. Somebody Shut His Front Door
Mayer's "napalm" comment from the notorious Playboy article wasn't even the most offensive thing he said in the interview. He also made disturbing comments about interracial dating, referring to his privates as "David Duke" and joking that he was going to "start dating separately" from his member. How gallant of you, John.