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More than two decades since scoring his big break, John Mayer is no stranger to making a public apology.

Mayer became a household name in the early 2000s after releasing hit albums Room for Squares and Heavier Things. He’s earned critical acclaim — and won seven Grammy Awards — throughout his career, but he’s also sparked his fair share of controversies over the years.

From his eyebrow-raising relationships with Jennifer Aniston and Taylor Swift to his past use of racist language, Mayer’s reputation is tinged with scandal. Following a brief hiatus from the spotlight, Mayer addressed his public “downfall” in a candid interview with The New York Times.

“I started to invent my own grenade,” he mused in 2017, reflecting on the reverse effect of wanting to avoid the “clichéd rock star” image earlier in his career. “What I did was probably semiconsciously just reboot it — control, alt, delete. … It was cat and mouse. And the mouse lost.”

Scroll down for a recap of Mayer’s biggest scandals and controversies through the years:

Jennifer Love Hewitt Stand-up

Mayer made a surprise appearance at The Laugh Factory in Los Angeles in 2006 — and took a swipe at his ex, whom he dated in 2002. He quipped that the pair never had sex due to a bad bout of food poisoning, but the joke didn’t land. “It really was me making fun of myself,” Mayer later told Us Weekly, calling himself “a wimp.”

It was long rumored that Hewitt was the inspiration for Mayer’s hit “Your Body Is a Wonderland,” but both parties have dispelled the speculation. “I had never met a celebrity when I wrote that song,” Mayer claimed in a 2022 “Call Her Daddy” interview.

Using the N-Word on the Record

Mayer gave two highly criticized interviews in 2010, one of which was featured in an issue of Playboy. “Someone asked me the other day, ‘What does it feel like now to have a hood pass?'” he told the outlet. “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-word] pass. Why are you pulling a punch and calling it a hood pass if you really have a hood pass?”

He added: “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.'”

Amid backlash, Mayer took to Twitter to apologize for using the “emotionally charged” slur. He also committed to being less “raw” in his interviews, saying, “It started as an attempt to not let the waves of criticism get to me, but it’s gotten out of hand and I’ve created somewhat of a monster.”

Calling Jessica Simpson ‘Sexual Napalm’

In the same Playboy interview, Mayer shared his unfiltered thoughts about his romance with Simpson. The pair dated from 2006 to 2007.

“That girl is like crack cocaine to me. Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm,” he said. “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.'”

Simpson addressed the jaw-dropping interview in her 2020 memoir, Open Book, confessing that she was “floored and embarrassed” by Mayer’s words. “He talked about me by name in the most degrading terms,” she wrote.

Following the tell-all’s release, Simpson exclusively told Us that she “didn’t expect” to hear from Mayer (or any other famous exes) about what got published. “They all know these stories, so I don’t think any of this came as a surprise to any of them,” she explained in February 2020.

Jennifer Aniston Breakup Comments

Mayer spoke to Rolling Stone for his second now-infamous 2010 interview, name-dropping Aniston and calling their breakup “one of the worst times of my life.” (The former couple dated on and off from 2008 to 2009.)

“How could I ever cosmically relate these two people?” Mayer said, comparing Aniston to a woman he’d met in Las Vegas. “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?”

Mayer once again referred to Aniston in his 2010 Playboy interview, implying that she couldn’t keep up with technology. “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. … I think she’s still hoping it goes back to 1998,” he said.

Taylor Swift Relationship Fallout

Perhaps one of Mayer’s most-talked-about relationships is his fling with Swift, whom he collaborated with on his song “Half of My Heart.” She was 19 when they briefly dated in 2009, and Mayer was then 32.

Swift went on to write a seething breakup song titled “Dear John,” which appeared on her 2010 record, Speak Now. “Don’t you think I was too young to be messed with?” she asks in the tune. (Speak Now was rereleased in July 2023 amid Swift’s quest to obtain ownership of her masters.)

Mayer dropped his own song seemingly inspired by Swift, “Paper Doll,” but not before calling out her songwriting. “It made me feel terrible,” he told Rolling Stone 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 will say as a songwriter that I think it’s kind of cheap songwriting.”

Fans of Swift have long held a grudge against Mayer, but she has rarely spoken about the relationship. During one of her June 2023 Eras Tour stops, Swift reminded her fans to be kind to the subjects of her songs.

“I’m 33 years old. I don’t care about anything that happened to me when I was 19, except the songs I wrote. … So, what I’m trying to tell you is that I’m not putting this album out so that you should go and feel the need to defend me on the internet against someone you think I might have written the song about 14 million years ago,” she said on stage.

Cultural Appropriation Accusations

Mayer attempted to transform his image with his 2017 comeback record, The Search for Everything. However, the music video for “Still Feel Like Your Man” was released to mixed reviews — and claims of cultural appropriation.

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When speaking about the song, Mayer told The New York Times that he felt an “ancient Japanese R&B” vibe from the guitar sound, which inspired him to create a “disco dojo” for the video. He danced with panda mascots and mimicked martial arts moves.

“Part of cultural appropriation is blindness,” he told the newspaper, claiming the production of the video was as “sensitive” as possible. “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.”

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