The Shady Side Of Chappell Roan

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After years of hard graft on the music circuit, Chappell Roan finally broke through to the mainstream with her 2023 debut album, "The Rise and Fall of a Midwest Princess." She reached the US Top 10 with singles "Good Luck, Babe," "The Giver," and "The Subway," launched a hugely successful nationwide tour, and picked up best new artist at both the MTV Video Music Awards and the Grammys.

But the artist born Kayleigh Rose Amstutz has become just as renowned for her outspoken behavior as her musical talents. You can barely pick up a tabloid these days without seeing the Missouri native's oft-heavily painted face staring back at you, with a certain soap opera sparked by a Brazilian hotel breakfast fast becoming a major talking point this year. From calling out her fellow big pop stars and unwittingly celebrating high-profile bigots to rivaling J.Lo for backstage diva demands and potentially telling fibs about her rags-to-riches journey, here's a look at 11 times Roan got super shady.

An international soccer player, an Oscar-nominated Hollywood favorite, and a reportedly overzealous security guard. These are just a few of the ingredients that, in March 2026, landed Chappell Roan on the front pages for all the wrong reasons.

The drama began while Roan was enjoying a hotel breakfast ahead of performing at Lollapalooza Brazil. According to Italian midfielder Jorginho, who was also staying at the same São Paulo establishment, the singer took umbrage with his 11-year-old stepdaughter — also the daughter of Jude Law — having the sheer audacity to smile in her direction as they passed her table and sent over security to have a word. To make the situation worse, these words were apparently delivered so aggressively they made the young girl cry.

Following a significant backlash in the press, Roan felt compelled to put her side of the story across in an Instagram post. The "Hot To Go!" hitmaker claimed that she had no part in the security's conduct and that he wasn't part of her official team. "I'm sorry to the mother and child that someone was assuming something that you would do something, and that if he felt uncomfortable, it makes me really sad," she added (via The Guardian). "You did not deserve that." This apology was also backed up by the guard in question, Pascal Duvier, who admitted that he'd taken it upon himself to confront the youngster.

Ahead of the 2024 presidential election, Democratic nominee Kamala Harris tried to jump aboard the Chappell Roan bandwagon by referencing her track "Femininomenon" for a campaign promo and even replicating her baseball cap design for some official merch. It doesn't appear as though the chart-topper, however, was particularly taken with this tie-in.

Indeed, Roan turned down an invite to perform at a Pride event staged at the White House. And then she refused to endorse Harris while speaking about politics in an interview with The Guardian. "I have so many issues with our government in every way," she said. "There are so many things that I would want to change."

But it was Roan's assertion that "there's problems on both sides" that received the most attention. The singer was accused of betraying the LGBTQ community, in particular, a large section of her fan base, by appearing to equate the Democrats with a Republican party that's generally perceived to be opposed to marginalized groups. She later argued on TikTok that some of her comments had been taken out of context, but she still refused to publicly back Harris, adding, "I don't agree with a lot of what is going on with policies — obviously, f*** the policies of the right, but also f*** some of the policies on the left. That's why I can't endorse. That's why I can't put my entire name in my entire project behind one."

In 2024, Chappell Roan took to Instagram in an attempt to put clear boundaries between her professional and personal life. And while the majority of readers agreed with what she had to say about fans who overstep boundaries, some believed she was tarring all of her supporters with the same brush.

"When I'm on stage, when I'm performing, when I'm in drag, when I'm at a work event, when I'm doing press ... I am at work," Roan declared (via Vogue) about the time she's more amenable to interactions. "Any other circumstance, I am not in work mode. I am clocked out. I don't agree with the notion that I owe a mutual exchange of energy, time, or attention to people I do not know, do not trust, or who creep me out — just because they're expressing admiration."

This wasn't the first time that Roan had addressed the subject on social media. Just a few days earlier, she hit TikTok to call out those who'd fostered parasocial relationships with her. "It's weird how people think that you know a person just because you see them online and you listen to the art they make," said the singer (via BBC News), who insisted she wasn't referring to a particular encounter at the time. "I don't [care] if you think it's selfish of me to say no for a photo or for your time or for a hug. That's not normal, that's weird."

Chappell Roan didn't exactly endear herself to her European fans in 2024 when she postponed a show in Berlin and outright canceled gigs in Amsterdam and Paris at the last minute. And "The Subway" singer made things even worse when news emerged of exactly why.

Roan had acknowledged on X that scheduling conflicts had been to blame for the sudden changes to her tour itinerary, adding, "I am so sorry and very disappointed I promise I will be back. I'm heartbroken. Thank you for understanding." But few were in an understanding mood when, on the day she should have been performing in the French capital, she posted an Instagram photo taken during rehearsals for the MTV Video Music Awards, where she'd received four nominations.

"I just find it so cringe that you think you're just allowed to disrespect your fans who spent money on housing and transportation to go see your show just because little miss ma'am preferred to go sing at the VMAs?" came one disgruntled response (via The Independent). "She had to make sure European fans who bought tickets to her tour before she even became famous knew she ditched them for an award performance she wouldn't have had the occasion to do if it wasn't for them," came another. Roan may well have believed the fallout was worth it, however, when she was crowned best new artist.

While Brigitte Bardot achieved iconic status thanks to her sense of glamor, beauty, and expression of sexuality, the French model, actor, and animal rights activist later became more renowned for her right-wing remarks, with everyone from the Muslim community to the #MeToo movement incurring the wrath of the increasingly problematic star. Unfortunately for Chappell Roan, this development seemingly passed her by.

Following the Parisian's death at the age of 91 in 2025, Roan decided to pay what she no doubt believed was an innocuous tribute on Instagram. "Rest in peace Ms. Bardot," she wrote (via Newsweek) before acknowledging how the '60s sex symbol had inspired and been explicitly referenced in the early song "Red White Supernova" ("She was a playboy, Brigitte Bardot / She showed me things I didn't know").

Of course, Roan was soon called out for celebrating such a controversial figure, causing the singer to remove the offending post and issue an explanation. "Holy s*** I did not know all that insane s*** Ms. Bardot stood for," she wrote in an Instagram Story (via Variety). "I do not condone this. Very disappointing to learn." However, even then, some fans weren't happy, with one remarking on Threads, "Instead of applauding that Chappell Roan is regretting writing a song about Bardot, maybe applaud the smart, hard work that a LOT of talented artists do to research before they use someone potentially controversial in their art."

Hell hath no fury like the online mom community scorned. And the oft-tragic Chappell Roan found that out to her cost in 2026, when during a guest appearance on Alex Cooper's phenomenally successful podcast "Call Her Daddy," she essentially claimed that contentment and parenthood were mutually exclusive terms.

"All of my friends who have kids are in hell," Roan told the host (via NME) when asked about the possibility of starting a family. "I actually don't know anyone who's happy and has children at this age. I literally have not met anyone who has light in their eyes, anyone who has slept." Of course, in the nuance-free social media age, many mothers took this as a personal slight, with one Instagram commenter posting, "As women we should not be picking each other apart, but raising each other up. Disappointed."

While Roan didn't respond to this particular furor, she did feel compelled to explicitly confirm, "I do not hate children," in an Instagram Story (via Pitchfork) following the São Paulo debacle in which she was accused — wrongly, as it seems — of sending her security guard to yell at an 11-year-old fan.

Chappell Roan made a dramatic appearance at the 2025 Fashion Los Angeles Awards, rocking up to the ceremony in a striking outfit from Alexander McQueen's Fall collection, which looked like she'd just stepped off the set of a Victorian horror film. However, it was her behavior, rather than her unique sense of style, on the red carpet that ended up grabbing all of the headlines.

The press had a field day thanks to an incriminating clip that appeared to show Roan, who looks totally unrecognizable without makeup, physically pushing her assistant away. The incident happened when the pair accidentally collided while the singer was waving at the crowd. And while the assistant tried to awkwardly laugh it off, Roan seemingly decided to use her hands to put further distance between them.

"It was an emotional and psychological push, with her hand there to infer of a push ... truly sinister," one social media user commented (via the Daily Mail). "Even if she didn't push her it was still rude, remarked another. "It's clear the woman was trying to go one way and didn't see Chappell, moving her out the way like that was unnecessary."

Move over, Jennifer "entirely white dressing room" Lopez. Step aside Mariah, "I don't do stairs" Carey. There's a new backstage diva in town. According to various sources, despite only recently graduating to pop's big league, Chappell Roan is already quite the prima donna when it comes to her rider requests.

"These weren't just basic rooms with a couch," an anonymous source told the Daily Mail about the "Pink Pony Club" singer's requirements ahead of a performance at Australia's Laneway Festival. "They were roped off, styled, and fully stocked: food, alcohol, everything you could think of." In fact, Roan was apparently so high-maintenance that an entire team of runners was tasked with making sure each of her needs was fulfilled.

And it's not just behind the scenes where Roan apparently likes to lay down the law. Following a verbal altercation with a photographer on the red carpet of the Rock and Roll Hall of Fame in 2024, the singer reportedly insisted that anyone with a camera at the 2025 ceremony behave themselves, otherwise she'd make a swift exit. Although this stipulation was greeted with laughter, it was still adhered to, and Roan's entrance came and went without a hitch.

Charli XCX (who's written more famous songs than you thought) and Chappell Roan now appear to be the best of friends. The latter even showed up to do the famous "Apple dance" duties during the former's performance at Barcelona's Primavera Sound festival in 2025. And the Brit, whose profile skyrocketed after engineering a Brat summer, also reached out to the American to offer her some sisterly advice once she, too, was propelled onto pop's A-list. But their relationship came under scrutiny in 2024 thanks to a piece in Rolling Stone.

While talking to the publication, Roan recalled being guided by Sir Elton John on how to stay true to yourself. "That's why I am saying no to every f***ing brand deal right now," she explained. "Because I'm like 'Does it fit in this world?' No, H&M does not fit in this world. Also, f*** H&M. No amount of money is going to [make me] consider working with [anyone]. It has to be a hundred percent right."

As well as offending the aforementioned clothing retailer — even though she was ironically cited as one of the worst-dressed celebs at the 2026 Grammys — Roan may well have offended Charli XCX. For the "Boom Clap" singer had only recently agreed to perform a show for and promote the company. "Those clothes gave me an ownership of who I was and what I wanted to project outwardly," she told British Vogue about her long-standing affinity. "In some cases, those clothes gave me confidence. That time was really formative for me."

Perhaps in a bid to boost her relatability, Chappell Roan has often claimed to have struggled financially before making it big. She's discussed living in a trailer park, for example, and while accepting the best new artist Grammy in 2025, she recalled (via Vogue) the hardships she faced during lockdown: "I was signed as a minor, [and] when I got dropped I had zero job experience under my belt. And like most people I had a difficult time finding a job during the pandemic and could not afford health insurance."

However, it turns out that Roan may have been laying it on a bit thick. Yes, she and her family did spend some time in a trailer park, but only on a temporary basis, and her parents went on to run a hugely successful veterinary firm. Meanwhile, her grandfather Dennis Chappell co-founded an insurance agency which now boasts revenues of up to $10 million.

"Chappell Roan's family is worth hundreds of millions of dollars but she couldn't afford health insurance after getting dropped by her label when she was like 22 (and young enough to still be on her parent's health insurance)," tweeted one social media skeptic (via the Daily Mail) as question marks about her upbringing started to surface. "Oh wow, Chappell might come from more money than any other pop girl," commented another.

Chappell Roan may now be a loud and proud member of the LGBTQ community. But as she admitted to Rolling Stone in a candid 2024 interview, this wasn't always the case. Despite identifying as queer herself, the self-proclaimed Midwest Princess once had a fear of a specific group within the community.

"I was scared of flamboyantly gay people because I was taught that," revealed Roan, after noting how she'd grown up in a staunch Republican household. Luckily, the star was soon able to shake off such prejudices. "[I realized] people hate flamboyantly gay people because it just exudes femininity, and people hate women. Just little things like that, you're like, 'Oh my God, this is just so f***ed.'"

Roan, who's invited drag queens to support her on tour and pretty much described herself as one, too, also acknowledged that she's still trying to come to terms with her own sense of self. "It took a lot of unlearning, and there's still things I'm still confused about, and [it's] why I feel so uncomfortable being gay sometimes. I don't get why this is such an issue for me. It shouldn't be, but something's just going on and I need to just accept that." Here's a look at everything Roan had said about her own sexuality.