How John Mayer became so hated in Hollywood

When John Mayer burst onto the music scene with Room For Squares in 2001, he was almost universally adored: Affable, handsome, hilarious, talented, and romantic. Unfortunately for the "No Such Thing" singer, the public admiration didn't last very long. What happened? It turns out, there were a lot of things at play, but thankfully, he may be able to make a serious comeback if he plays his cards right.

He disrespected Jessica Simpson...

After he and Jessica Simpson, who he dated from 2006 to 2007, broke up, he dissed her, hard. He told Playboy in February 2010 (via E! Online), "Yeah, that girl is like crack cocaine to me. Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm." That's not all he said, though—even though it was bad enough. He added, "There are people in the world who have the power to change our values. Have you ever been with a girl who made you want to quit the rest of your life? Did you ever say, 'I want to quit my life and just f**kin' snort you? If you charged me $10,000 to f**k you, I would start selling all my s**t just to keep f**king you.'"

Uh, yikes.

...and she hasn't forgiven him for it

Simpson didn't take the interview lightly. She told The View in March 2010, "I'll walk in to a restaurant or something, and I notice that more men are looking at me, and I feel like they're undressing me, and that's embarrassing." When asked if she'd spoken with Mayer since the story hit, she scoffed, "Oh no, he'll never have this napalm again!" She added, "He did apologize, but at this point, it doesn't really matter."

She also told Oprah Winfrey, "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…absolutely, I felt betrayed. I hope he gets his life together. I'll be praying…He apologized, [but] I haven't written back. I don't accept it. I don't resent him, but that part of my life — I'm letting it go." She added (via People), "There's nothing worse than being disappointed in somebody…I'm a little bit angry. I don't want people to know how I am in bed."

He publicly spoke about his split with Jennifer Aniston

During a "break" in Mayer's relationship with Jennifer Aniston, who he dated from 2008 to 2009, he blabbed to press about what ended up being a temporary split.

"It's the most normal thing in the world, there's no lying, there's no cheating, there's no nothing. If you guys are going to run stuff and run every lie under the sun…Have somebody stand up for somebody. Have me as a man who ended a relationship," he ranted (via the Telegraph). "Write that Jennifer Aniston is the smartest most sophisticated woman I've ever met. People are different, people have different chemistry, they have different lives. It's not about years, it's about going out with somebody, being truthful on the way in, being truthful in the middle and being truthful on the way out. You're either a cheater, or you break up, and I'm not the first, I'm the second one. And that's it, there's no lying, there's no bulls**t."

...and later dissed her about their age difference

Mayer also dished to Playboy in 2010 about his relationship with Jennifer Aniston, who he dated in 2008 and 2009, basically saying their age was a problem — he wanted to be young, wild, and free, and Aniston wanted to be serene, domestic, and private. "That woman was the most communicative, sweetest, kindest person. I'll always be sorry that it didn't last. In some ways I wish I could be with her," he said (via E! Online). "But I can't change the fact that I need to be 32…I don't want to pet dogs in the kitchen." (Aniston was 39 at the time.)

He continued, "One of the most significant differences between us was that I was tweeting. There was a rumor that I had been dumped because I was tweeting too much. That wasn't it, but that was a big difference," he admitted. "The brunt of her success came before TMZ and Twitter. 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.' You have to show that you don't take yourself seriously." Doesn't that sound a little ageist to you? It should — and if Andy Cohen is to be believed, Aniston still doesn't quite forgive Mayer for running his mouth so much.

Taylor Swift's 'Dear John' hurt him

After splitting from Aniston for good in 2009, he had a brief but intense relationship with Taylor Swift from late 2009 to very early 2010 after collaborating on his song "Half Of My Heart," and there's still, er, bad blood between them to this day. After Mayer allegedly broke her heart, Swift lashed out in her not-so-subtle song "Dear John" off of Speak Now in 2010, including lyrics like, "Don't you think I was too young to be messed with / The girl in the dress cried the whole way home" and "You'll add my name to your long list of traitors who don't understand / And I'll look back in regret I ignored what they said / 'Run as fast as you can.'"

The song became one of the most popular ever among Swift's country-pop fanbase, much to Mayer's chagrin — because at the time, Swift was America's untouchable sweetheart. He told Rolling Stone in summer 2012, "It made me feel terrible, because I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do." He added, "I never got an e-mail. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I'd already been dressed down. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?"

His ire didn't end there, and he attacked her artistically, too. "As a songwriter I think it's kind of cheap songwriting. I know she's the biggest thing in the world, and I'm not trying to sink anybody's ship, but I think it's abusing your talent to rub your hands together and go, 'Wait till he gets a load of this!' That's bulls**t." C'mon, man — don't give her the satisfaction of acknowledgment! He could have easily denied being the subject of the track if he didn't get defensive.

He has weird attitudes about women in general

Notorious playboy Mayer told Playboy (via Us Weekly), "I hate being the heartbreaker. Hate it. If I date somebody and it doesn't work out, it's another nightmare for me." Doesn't it seem more like a nightmare for them?

It doesn't end there. When Playboy asked Mayer how many women he'd bedded since splitting with Aniston, he replied, "I'm going to say four or five. No more. But even if I said 12, that's a reasonable number. So is 15. Here's the thing: I get less a** now than I did when I was in a local band. Because now I don't like jumping through hoops."

He also told Rolling Stone in 2010 that because of the women he'd dated in the past, meeting anyone new who wasn't a celeb was hard. "All I want to do now is f**k the girls I've already f**ked, because I can't fathom explaining myself to somebody who can't believe I'd be interested in them," he said. "I'm too freaked out to meet anybody else."

Fair enough, but then it gets crass. "I met a girl one time in Vegas. Her name was Dimples, and the 's' in Dimples was a dollar sign," he said. "I have this weird feeling, a pride thing, for the people I've had relationships with. I still feel like I'm with them, in the sense that if I f**ked Dimples, what does that say about someone like Jen? I feel like it's all connected. How could I ever cosmically relate these two people?"

He added, "What would I be saying to Jen, who I think is f**king fantastic, if I said to her, 'I don't dislike you. In fact, I like you extremely well. But I have to back out of this because it doesn't arc over the horizon. This is not where I see myself for the rest of my life, this is not my ideal destiny,' and then I see myself f**king Dimples? What does that say for my case?"

He may have used his girlfriends for press

Publicity legend Rob Shuter, who previously worked with Jessica Simpson, revealed that he thinks Mayer loved the publicity he got from his high-profile lady loves.

Shuter told New York Magazine, "John at times claimed that he disliked the press, so when [he and Simpson] broke up, I think she felt that the press broke them up. But I think we've learned now that nobody likes the press as much as John Mayer does," he said. "The only time we ever got to see Jennifer Aniston out was when she was dating him, and he used to march her from La Esquina to his apartment, and that was for blocks. That girl never, ever gave photographs, and suddenly there's literally a marching press corps that's following her down the street," he continued. "Jennifer Aniston. She's like a stealth bomber. As long as I've been doing this, you never get pictures of Jen unless she wants you to."

Shuter added, "I remember when I was working with Alicia Keys, and John was working with her…At the time, his publicist was very aggressive about making sure that John wanted more attention: 'John likes press, he likes to do interviews, he likes being on magazine covers.' Which he wasn't until he started dating Jessica," Shuter pointed out. "After that, my goodness, he just dated celebrities constantly."

He may have used Katy Perry for PR, too

Mayer may have used his relationship with Katy Perry to publicize his album, Paradise Valley. The couple collaborated on his track "Who You Love," and even though he'd said he and the "Roar" songstress had a "private relationship," he had no problem toting her along on talk show appearances to promote their duet. Their appearance on Good Morning America was pretty awkward (that body language!), but the pair fared slightly better on Ellen, where he hijacked a big portion of what was supposed to be an interview with Perry.

His racially-charged comments

Another shortsighted bit from Mayer's Playboy interview? When he dropped the N-bomb. When asked if rappers like Kanye West, with whom he collaborated on "Bittersweet," accept him, he replied (via People), "Someone asked me the other day, 'What does it feel like now to have a hood pass?' If you really had a hood pass, you could call it a n****r pass. But I said, 'I can't really have a hood pass. I've never walked into a restaurant, asked for a table and been told, 'We're full.'" When called out, he almost immediately apologized on Twitter for using the slur, but the damage was done.

However, it wasn't his only racially insensitive remark in the interview. At one point, when asked if black women "throw themselves" at him, he replied (via Vulture), "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**kin' David Duke c**k. I'm going to start dating separately from my d**k."

His apology tour may have backfired

After the Playboy interview made headlines, Mayer lied low. When he finally came out to promote his next album, he acted contrite for his actions…but never actually came out and said he was sorry to the people he hurt.

He told Ellen DeGeneres in spring 2012, "It was a very strange time and it sort of rocketed me into adulthood. It was a violent crash into being an adult. So for a couple of years it was just figuring it all out, and I'm glad I actually stayed out of the spotlight. Because I think back then I would've said, 'Give me two weeks or let me get out and do Ellen and let me explain myself.' It was like, 'No, idiot. Go away and be 33 and 34 instead of 28 for the fourth year.'" He added, "I just sort of lost my head for a little while."

Days later, he told NPR's All Things Considered (via People), "I had nothing to say — I was going through a time in my life where I didn't really want to share what was going on, but I didn't want to be boring. I remember thinking to myself, 'We gotta give a Rolling Stone interview; I don't want anybody at Playboy to think this is a boring interview.' I got those lines so crossed, that what you read—among other things, obviously—is this complete miscalculation in why I was asked to do the interview." He added, "I wasn't prepared to be honest, but I knew that I had to be open. When you're just open but not honest, then you start free-associating garbage. It doesn't mean I can go back and scrub it out, but I understand it [now]."

He was too desperate for approval

In February 2013, Mayer admitted to CBS Sunday Morning, "I was just a jerk. It's very liberating when you finally realize it's impossible to make everyone like you. I wanted everybody to like me. I thought I was one shuck and jive away in every direction."

Mayer had previously told All Things Considered (via People) that he was obsessed with the public perception of him. "[My thought process at the time was] 'I've got to change their minds.' I'd read comments [that said], 'He's a d-bag.' And then you go, 'No, I'm not!' If you're a control freak you [think], I'm going to figure out a way to make that one guy say, 'He's not all that bad.'"

In March 2015, Mayer explained on the Today show, "I'm a recovered ego addict. The only way that I can be sure that I don't relapse is to admit that I constantly have this ego addiction — every day…The greatest moment for me was giving up the big fight, the big fight to be this thing that gets off the airplane at LAX and floats through."

As recently as November 2016, Mayer admitted in a Facebook Live video, "I get the most flattered and moved when I look at Instagram hashtags. I feel like that's a kinder, gentler Internet."

His sense of humor didn't translate well

Mayer dabbles in standup comedy, but it hasn't made him a ton of friends. In 2009, comedian Kumail Nanjiani, who's gone on to star on Silicon Valley, told a story of Mayer bumping him off of a comedy show to do five minutes onstage — and that five minutes turned into 20 minutes. When Nanjiani finally got to go onstage, Mayer reportedly heckled him and called him "Kabul" and said that "he looked like a brown guy but sounded like a white guy."

Mayer then offered up a half-hearted apology for the incident, telling The Comic's Comic, "I felt really bad. I felt like I ruined his set [The situation was] combative in the sense that the crowd didn't really accept the fact that the jock, the guy who gets the girls, was at a place where the guys go who talk about how they don't get the girls." For someone who sings a song called "My Stupid Mouth," you'd think he'd know when to shut it.

His general TMI habit

Within one 2010 Rolling Stone interview, readers learned about Mayer's fascination with "poop Twitters" (don't Google them), his porn habits (hint: he looks at a lot of it), obsessive masturbation, and his sex dreams (in which paparazzi make him unable to perform). He admitted at the time, "I don't know how much further I can do this before I'm a dead body on the side of the road. I mean, either I'm a total f**king nut case who can explain himself, or I'm really not crazy and I can explain myself. I don't know yet."

How he can turn it around

Every so often, Mayer will make headlines for doing something awesome, like in April 2013 when he helped build homes for veterans, or in July 2013 when he gifted a fan with a guitar, or in October 2015 when he gave away 10,000 tickets to see him perform with Dead & Company. Even as far back as 2010 when he was most reviled, the Isaac Foundation, with whom Mayer worked previously, defended the Grammy winner as a "kind, caring, and compassionate person." He even collaborated on a laundry line for charity in 2016.

Above all things, Mayer is an incredibly talented musician. Continuum is a masterpiece, and his other works are well worth repeat listens as well. If he can keep his nose to the grindstone and his mug out of gossip headlines (unless it's for something deliberately silly, like his hilarious skincare video, or for his impromptu jam sessions with willing comedians), his music will ultimately be his legacy instead his lack of media training.