John Mayer has been accused of sexism and racism throughout his career. Here's a timeline of the sin

• John Mayer has weathered a variety of controversies throughout his career.
• Anecdotes from ex-girlfriends paint the "New Light" singer as toxic and manipulative.
• He was also widely criticized for a 2010 interview with Playboy, in which he used the N-word.

John Mayer has made headlines recently for a seemingly tame series of events: voicing support for Britney Spears, joining TikTok, and performing at the 2021 Grammy Awards.

However, while Mayer's current persona may not seem contentious, it's marred by a series of controversies throughout his career.

The "New Light" singer, who burst onto the music scene with 2001's "Room for Squares," quickly became known for giving "raw" interviews and being "in love with the sound of his own voice." His rap sheet includes troubling anecdotes from ex-girlfriends, which suggest a pattern of toxic behavior, several racist remarks, and accusations of cultural appropriation.

Insider compiled a timeline of Mayer's offensive comments and backlash he's received over the years.

2006: Mayer made lewd comments about Jennifer Love Hewitt during a live-comedy routine

Mayer's first brush with notoriety came during a surprise appearance at The Laugh Factory in Los Angeles.

His stand-up set included a pointed jab at his ex-girlfriend, Jennifer Love Hewitt, whom he dated in 2002. It was widely assumed that Mayer's hit song "Your Body Is a Wonderland" was inspired by the "Ghost Whisperer" actor. 

However, Mayer claimed onstage that he never got to have sex with Hewitt, due to a bout of food poisoning.

The monologue raised eyebrows, as some critics accused Mayer of objectifying Hewitt. He later issued a public apology to his ex, telling Us Weekly, "It really was me making fun of myself," adding, "I'm a wimp."

2008: He made sure everyone knew that he dumped Jennifer Aniston, saying he 'burned the American flag'

Mayer and Jennifer Aniston reportedly met at an Oscar party in 2008 and dated for about a year.

The couple also split briefly in the summer of 2008, when Mayer held an impromptu press conference outside his New York gym. The 30-year-old musician told reporters that he broke up with Aniston "because I don't want to waste somebody's time if something's not right."

"I'm the asshole. I burned the American flag. I basically murdered an ideal," he said.

As Rolling Stone noted, Mayer's mea culpa was not well-received: "He came off like a jerk only interested in taking credit for the breakup."

Mayer later said his comments "really, really upset" Aniston.

"I wanted to take responsibility for having ended it because I saw it as such an offense," he told Playboy. "But a lot of people felt I was saving face. "

2009: Mayer threatened to 'forcefully sodomize' an interviewer's editor 

Mayer was interviewed by Vulture's Christianna Ablahad during a party for Giorgio Armani's home label, where the "Daughters" singer was "playing host."

While asking Mayer about his take on current events, Ablahad opined that President Barack Obama's Nobel Peace Prize was premature. Mayer replied, "I love you, you're beautiful, but shut your fucking mouth."

"You're not building a journalistic career. You're making yourself look like a moron and you're not a moron," he said.

He concluded the interview by declaring, "I'm going to forcefully sodomize your editor."

2010: Mayer made numerous misogynistic comments in an interview with Rolling Stone

Mayer starred on the cover of Rolling Stone's February 2010 issue. He discussed a variety of topics with the magazine, including self-pleasure ("I am the new generation of masturbator") and fame ("I love being the center of attention").

The musician, then 32, said he was looking to date a woman with "a beautiful vagina."

"Aren't we talking about a matrix of a couple of different things here? Like, you need to have them be able to go toe-to-toe with you intellectually," he said. "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?"

Mayer also name-dropped Aniston, calling their breakup "one of the worst times of my life" and using her to explain how he decides if a woman is acceptable to sleep with.

"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 fucked 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 continued: "What would I be saying to Jen, who I think is fucking 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 fucking Dimples? What does that say for my case?"

2010: He called Jessica Simpson 'sexual napalm' and used the N-word in an interview with Playboy

Shortly after the Rolling Stone interview was published, Mayer made more offensive remarks in the March 2010 issue of Playboy.

A notable chunk of the interview was dedicated to Jessica Simpson. The couple was first linked in 2006 and dated on and off for years, but split for good when he referred to her as "sexual napalm."

"That girl, for me, is a drug. And drugs aren't good for you if you do lots of them. Yeah, that girl is like crack cocaine to me," Mayer told Playboy. "Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm."

He added: "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 fucking snort you? If you charged me $10,000 to fuck you, I would start selling all my shit just to keep fucking you.'"

Simpson later said she was "floored and embarrassed" after the interview was published.

"He talked about me by name in the most degrading terms," she wrote in her memoir. "I scanned it more than I read it, horrified at whatever paragraph my eyes landed on."

Mayer also implied that Aniston, who is eight years his senior, was an out-of-touch technophobe during their relationship.

"If Jennifer Aniston knows how to use BitTorrent, I'll eat my fucking shoe," he said. "One of the most significant differences between us was that I was tweeting. There was a rumour that I had been dumped because I was tweeting too much. That wasn't it, but that was a big difference."

"The brunt of her success came before TMZ and Twitter," he added. "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.'"

Mayer also shared some deeply problematic thoughts on "being Black" and casually used the N-word.

"Someone asked me the other day, 'What does it feel like now to have a hood pass?" Mayer said. "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 n----- pass. Why are you pulling a punch and calling it a hood pass if you really have a hood pass? But I said, 'I can't have a hood pass. I've never walked into a restaurant, asked for a table and been told, 'We're full.'"

Although Mayer later apologized on Twitter for using the "emotionally charged" slur, he never addressed his other racist remarks — like comparing his penis to David Duke, a former grand wizard of the Ku Klux Klan.

When asked whether Black women "throw themselves" at him, Mayer replied, "I don't think I open myself to it. My dick is sort of like a white supremacist."

Additionally, when asked whether he'd ever kissed a man, Mayer used a slur for gay people.

"I remember seeing Perez Hilton flitting about this club and acting as though he had just invented homosexuality. All of a sudden I thought, I can out-gay this guy right now," Mayer told Playboy. "I grabbed him and gave him the dirtiest, tongue-iest kiss I have ever put on anybody — almost as if I hated f--s."

2012: He slammed Taylor Swift for 'Dear John,' calling it 'cheap songwriting'

Mayer and Taylor Swift dated briefly in 2009. He was 32 years old, while she was 19.

She released the searing breakup ballad "Dear John" in 2010, which is widely assumed to describe the pair's toxic power dynamic, although Swift has never confirmed the song's inspiration.

"Dear John, I see it all now, it was wrong / Don't you think 19's too young / To be played by your dark, twisted games / When I loved you so?" she sings in the chorus.

Two years later, Mayer complained to Rolling Stone that Swift "humiliated" him.

"It made me feel terrible," he told the magazine in 2012. "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."

"I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?" he said. "I will say as a songwriter that I think it's kind of cheap songwriting."

When asked about Swift's lyric, "Don't you think I was too young to be messed with?" Mayer said, "I don't want to go into that."

2013: After slamming Swift's songwriting, he released his own song referencing the relationship

One year after dismissing his ex's songwriting as "cheap," Mayer released "Paper Doll," a song largely believed to be a response to Swift's "Dear John." 

In "Dear John," Swift sings, "You paint me a blue sky / And go back and turn it to rain." Mayer retorted on his track with, "If those angel wings don't fly / Someone's gonna paint you another sky."

He also appeared to reference her 2012 hit song "22" with "You're like 22 girls in one." The following line, "And none of them know what they're running from," calls back to Swift's "Dear John" lyric: "I'll look back and regret / How I ignored when they said / Run as fast as you can."

Donna Kaufman dissected the song for "Today" at the time, writing, "Is 'Paper Doll' supposed to Mayer's revenge? Seems kind of petty, honestly — especially coming from a 35-year-old man to a 23-year-old girl." 

2017: Mayer was accused of cultural appropriation after releasing the music video for 'Still Feel Like Your Man'

After years of modest album sales and living under the radar in Montana, Mayer reemerged in 2017 with a new album, "The Search for Everything," and a comeback narrative.

The album's second single, "Still Feel Like Your Man," was released in February of that year. He told the New York Times that its guitar riff reminded him of "ancient Japanese R&B," so he visualized the music video as a "disco dojo."

Indeed, the clip features Mayer in a makeshift bamboo forest, dancing with two people in panda suits.

"I think we were as sensitive as we could possibly be," he told the Times. "It was discussed at every juncture."

"Part of cultural appropriation is blindness," he added. "I'm on the right side of the line because it's an idea for the video that has a very multiethnic casting, and nobody who is white or non-Asian is playing an Asian person."

All the same, Mayer was swiftly accused of perpetuating Asian stereotypes.

The video was met with headlines like "Here's What John Mayer Thinks a 'Disco Dojo' Looks Like" and "On a Scale of Problematic to Racist, How Bad Is John Mayer's New Music Video?"

"Mayer manages to hit every obvious Asian cliche over the course of the four-minute video. There's geishas, a martial arts scene, and sumo wrestlers, too," Nylon wrote.

Mayer offered a half-hearted explanation to USA Today, claiming he didn't expect "any backlash."

"We anticipate that somebody's going to have something to say about it, but that does not preclude you from creating something," he said. "You should not be an artist if your fear is that somebody, somewhere, if you Twitter-search it, is going to use the phrase [cultural appropriation]."

2018: Mayer implied he's unwilling to call himself a feminist

In an Instagram Q&A session with fans, Mayer answered a fan who asked, "What's your take on feminism?"

"My take is less about feminism and more about the issue of nomenclature, specifically how reductiveness of language can turn people off from noble and vital causes," he wrote.

"If you asked people if they support ensuring equal rights for women in all aspects of their lives, they would very likely answer yes. Change that question to 'are you a feminist' and the answers instantly become more complicated," he continued. "That's because a single phrase is being co-opted than the actual ideal it attempts to present."

Mayer concluded that he supports "equal rights for women in all areas," but is hesitant to use the actual label "feminist."

2018: He said he 'abused' his ability to seduce women in his 20s

Mayer, then 41, discussed his sex life on his Instagram Live show, "Current Mood."

He joked that he gets "rejected a lot" these days because he's seen as "PR poison," according to People.

"Yes, I could have sex with somebody at any moment. But being a famous man is somewhat similar to being a beautiful woman: there is access, there's very seldom any desire," Mayer said. "The older I get the less desirous I am of unsheathing new body parts."

"I actually find that people not being into me brings a real level of reality into my life," he continued. "Whereas when I was in my early 20s, where I couldn't really miss, I really kind of abused that. That's now out of the question."

He added: "I won't name names but not so long ago I gave a girl my number and she said, 'I probably won't use it.' I actually think it's awesome too because I would have ruined her."

2020: Simpson described Mayer's behavior as toxic and manipulative

Simpson addressed her relationship with Mayer for the first time in her memoir, "Open Book."

The "Irresistible" singer wrote that Mayer broke up with her no fewer than nine times, always via email. She also said he would try to control or "win" conversations, and that he regularly made her feel inadequate.

"He would tell me that my true self is so much greater than the person I was settling on being," Simpson wrote. "Like there was some great woman inside me waiting to come out, and I had to hurry up and find her because he wanted to love that woman, not me."

"I constantly worried that I wasn't smart enough for him," she continued. "I was so afraid of disappointing him that I couldn't even text him without having someone check my grammar and spelling."

"My anxiety would spike and I would pour another drink," she added, according to People. "It was the start of me relying on alcohol to mask my nerves."

Simpson told Tamron Hall that she doesn't expect a public apology from Mayer because he "can't take it back."

"I'm a very forgiving person, but I'm also honest," she said. "So, in the memoir, if I'm gonna talk about stuff that caused me pain, I'm going to be honest about it. And that was a time in my life that I was very manipulated and also in love, or seemingly."

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