Katy Perry and all the poor, unfortunate people who have fought legal battles against her.

There are a few things guaranteed to keep the celebrity news cycle ticking.

Examples include men (allegedly) doing bad things, messy divorces and Taylor Swift, just... broadly. Another MVP of the celebrity gossip world is Katy Perry — specifically, her penchant for rather absurd, unrelatable legal battles.

Katy Perry vs. a bedridden businessman.

In the latest legal drama, Katy Perry and Orlando Bloom have won a years-long legal battle against the bedridden businessman, Carl Westcott, over an AU$22 million, eight-bedroom, 11-bathroom mansion.

The dispute began in 2020 when Perry and Bloom purchased a home during the pandemic from Westcott — an 85-year-old businessman and army veteran who owned a phone-order flower company called 1-800-Flowers.

Westcott sued the couple's business manager, Bernie Gudvi, who acted on their behalf in the sale. He claimed he was heavily medicated and not of sound mind when he signed a contract to sell them the home for US$15m (AU$22m).

Katy Perry and Orlando Bloom bought the mansion during the pandemic. Image: Getty.

In court documents obtained by the Los Angeles Times, Westcott said he had a six-hour back surgery days before being presented with the proposed real estate contract and his strong medications made him "intoxicated" at the time of signing.

He had only been living in the home for two months at the time, and was seeking cancellation of the sale, as well as compensation for legal fees.

The case was heard in court, but Westcott wasn't there because he was reportedly bedridden with Huntington's disease.

Instead, his son, Court, and daughter-in-law, former Real Housewives of Dallas star Kameron Westcott, were present.

"We want justice for his dad and to defend his honour the best we can," Kameron told Radar Online. "He's such an honourable man. He's worked his entire life and deserves to stay in his home. It's sad Katy is trying to take that from him."

She said the family was concerned that Westcott would die before seeing a resolution.

Meanwhile, Perry and Bloom's team claimed Westcott was of sound mind during the sale and requested not only the home, but also millions of dollars in compensation for rent they could have charged on the property, and money they had to spend to maintain a different home while waiting to move in.

In May 2024, Perry won the case. However, the legal battle continues.

Watch Katy Perry perform with Tina Arena at the AFL grand final. Post continues after video.

Perry is suing Westcott for damages, claiming she lost $US2.7 million ($AU4.08 million) in potential rent because she could not lease out the mansion during the multi-year trial.

That amount has since been increased to $US5.5 million ($AU8.3 million), the New York Post reports, who said that Bloom was subpoenaed to give evidence.

Their court date is set for August and both Perry and Bloom are expected to testify.

Westcott's son, Chart, had some choice words for the singer ahead of the day.

"Katy Perry says she felt 'super connected to love' after her trip to space. I can't help but wonder if her experience will make her more compassionate to elderly disabled veterans like my father," Chart told the New York Post after Perry blasted into space for 11 minutes on board Blue Origin's NS-31 mission.

"I am glad she made it back safe and look forward to having her testify in August and be held accountable for her actions against my family."

This is a weird enough story on its own, but the thing is, if we had a dollar for each time Perry was involved in a contentious real estate issue with the elderly, we'd have two dollars.

That's not a lot of money, but it is weird that something so incredibly niche has happened twice.

Katy Perry vs. 2 Los Angeles nuns.

Sister Catherine Rose Holzman and Sister Rita Callanan in 2015. Image: Getty.

Before there was Westcott, a bedridden veteran, there were the nuns.

In 2015, Perry purchased a 32,000-square-metre convent in the LA neighbourhood of Los Feliz from the Archdiocese of Los Angeles, for about AU$22m.

But nuns who once lived on the property opposed the transaction, claiming they owned it and had struck a separate deal with restaurateur Dana Hollister.

In an attempt to make good, Perry met with them, but it didn't go well. One of them, Sister Rita Callinan, even shaded her in interviews, with zingers like, "I found Katy Perry and I found her videos and... if it's all right to say, I wasn't happy with any of it."

A judge ruled against the nuns the following year, declaring the sale to Hollister invalid — but the nuns did not back down quietly.

In 2018, amidst a heap of legal challenges, Sister Catherine Rose Holzman collapsed and died in court.

Sister Callanan told the New York Post that Sister Holzman's last words were: "Katy Perry. Please stop."

The following year, Sister Callinan declared Perry had "blood on her hands".

The sale to Perry was never completed.

Katy Perry vs. Katie Perry.

Now, thankfully, this battle doesn't involve a house.

But it does involve clothes, her namesake, and a judge who makes pretty good puns.

In 2009, Aussie fashion designer Katie Taylor (nee Perry) applied for the trademark of 'Katie Perry', a name she had been selling clothing under since 2007.

Katy Perry's lawyers initially challenged the claim, prompting Taylor to share a YouTube video asking Perry to allow them both to 'live their dreams'. Perry's team withdrew their opposition and Taylor's trademark was granted.

But years later, Perry used her name to sell merch while on tours to Australia in 2014 and 2018.

In 2019, Taylor initiated legal proceedings against Perry for trademark infringement, claiming 'Katy Perry' is 'substantially identical or deceptively similar' to 'Katie Perry'.

Katie Perry and Katy Perry's legal war has come to an end. Image: Instagram/@katieperry.clothing/Getty.

The case went to court, where emails between Perry and her manager Steven Jensen in which Perry disparaged Taylor were shown.

In the 2009 emails, Perry wrote "dumb b**ch" and "this b**ch won't stop", referring to Taylor's trademark application.

Jensen said it was an emotional response, not directed at Taylor personally.

"Katy Perry is an artist. Artists are emotional people. Emotions are what drive their talent," he said.

In 2019, Justice Brigette Markovic ruled mostly in Taylor's favour and described the case as a "tale of two women, two teenage dreams and one name" in her ruling.

Bet she was proud of that one.

Perry has since appealed the decision and she won. Taylor was ordered for her trademark to be deregistered.

But because it's the gift that just keeps on giving, the case is back. Now, in 2025, Taylor has been thrown a lifeline.

I guess Perry's lyrics, "Just because it's over doesn't mean it's really over" ring true.

Last week, Taylor scored a legal win when the High Court agreed to hear the case in a special leave application hearing in Sydney. This will allow her to try to overturn the Full Federal Court judgment made in November.

Taylor's barrister Christian Dimitriadis SC said the appeal judges had erred in their interpretation of Australian trademark law.

Just because Perry had a reputation as a pop star at the time the Katie Perry trademark was registered did not mean she also had a reputation for selling clothing at the time, he argued.

Taylor's barrister said she had been misfortunate to choose a trademark similar to someone who became famous, and someone who would later sell clothing in Australia knowing she was infringing on the mark.

He said it was incorrect of the Full Court to deregister the Katie Perry brand because it found the designer applied for the trademark knowing of the US singer's reputation.

Perry's barrister Matthew Darke SC argued that the High Court should not hear the case as it did not involve an important question of law.

However, the judge ultimately decided to hear Taylor out. So back to court they go.

The matter will be heard in the High Court later this year.

Read all about the news here and Australia's Katie Perry's side of the story here.

This article was originally published on September 28, 2023 and has since been updated with new information.

Feature image: Getty.