Top 10 Craziest Celebrity Court Cases



Top 10 Craziest Celebrity Court Cases

VOICE OVER: Phoebe de Jeu WRITTEN BY: Nathan Sharp
These are the craziest celebrity court cases of all time! For this list, we'll be looking at court cases involving famous people that were quite out there either by the nature of the case or the shocking details they revealed. Our countdown includes Oprah Goes to Court Over a Burger, Johnny Depp & Amber Heard, Bill Cosby Ruins a Stellar Reputation, and more!

Top 10 craziest celebrity court cases

Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 craziest celebrity court cases.

For this list, we’ll be looking at court cases involving famous people that were quite out there either by the nature of the case or the shocking details they revealed.

Which of these do you find the most memorable? Let us know in the comments below!

#10: Oprah Goes to Court Over a Burger


Did you know that you could get sued for making libelous claims against food? “How Oprah Got Sued for Dissing a Burger” may sound like an Onion article, but it was hilariously real. During one episode of her popular talk show, Oprah was speaking with a guest who was linking the consumption of beef to various neurodegenerative diseases. Cattle industry executives then sued Winfrey and her guest for falsely disparaging beef, claiming that their comments had cost them millions in lost revenue. It supposedly fell under Texas’s “food disparagement” law, so the case actually went to court. However, it was found that that particular law did not rightly apply to Oprah’s case, and she was acquitted by the jury.

#9: Katy Perry vs. Nuns


Turn this story into a miniseries, right now: Katy Perry tried purchasing an ex-convent in Los Angeles for nearly $15 million, but the sale got caught up in legal real estate complexities. In the late 2010s, a hearing was held to help clear up the convent’s disputed ownership. Unfortunately, one of the nuns, a Sister named Catherine Rose Holzman, reportedly collapsed and died in the court. Her last words were supposedly, “Katy Perry. Please stop.” The other nun, Sister Rita Callanan, then told Perry that she had “blood on her hands” owing to the sudden death of Holzman. Regardless, Perry ended up winning the battle and was awarded millions in legal fees.

#8: Anna Nicole Smith Fights for Her Husband’s Estate


Anna Nicole Smith was a very famous Playboy model who married an oil tycoon named J. Howard Marshall. They were married when Smith was 26 and Marshall was 89. Smith was viciously lambasted in the media and widely called a gold digger. The marriage lasted just thirteen months, as Marshall soon passed. Smith was left out of his will, but she claimed that Marshall had told her he would leave her his hefty stake in Koch Industries. The subsequent court case over Smith’s potential inheritance got very messy - with bankruptcy court attempting to become involved due to Smith’s filing. It was also very lengthy and eventually made its way to the Supreme Court. Unfortunately, Smith died of a prescription overdose before the case could be settled.

#7: Gwyneth Paltrow Falsely Advertises


She may be a good actress, but Gwyneth Paltrow’s reputation has largely been ruined by Goop. Her infamous lifestyle company sold various items like “quartz vaginal eggs” that supposedly helped with women’s sexual and mental health. Many people weren’t having it, claiming that the items were nothing but snake oil. In fact, the criticisms got so bad that Paltrow and her company were taken to court. The lawsuit argued that Goop’s medical claims were “unfounded” and scientifically inaccurate. Furthermore, touting the product’s so-called medical benefits supposedly fell under false advertisement. The prosecutors won the case, and Goop was ordered to pay nearly $150,000 in damages.

#6: Jussie Smollett Fakes a Hate Crime


“Empire” star Jussie Smollett shocked the world in January of 2019. Smollett claimed that he was the victim of a hate crime by two masked supporters of Donald Trump. However, holes were quickly poked in his story and the truth was revealed. Smollett had faked the attack and had paid two people to help him stage it. He was fiercely criticized and sued by the city of Chicago in April of the same year. They wanted the $130,000 they had spent investigating his fake crime back. After initial charges were dropped, a second trial began in November of 2021 and didn’t last long, with Smollett being found guilty of disorderly conduct through his false police reports. He was sentenced to 150 days in jail and over two years’ probation.

#5: Harvey Weinstein Sparks #MeToo


One of the major players in the Hollywood machine was taken down in October of 2017. Throughout that month, over eighty women accused producer Harvey Weinstein of inappropriate conduct - allegations that sparked both the #MeToo movement and the overall Weinstein effect. The resulting 2020 trial was bizarre. Weinstein showed up to court wielding a walker and complaining about severe back pain, while others claimed that he was trying to generate sympathy by appearing old and frail. The jury also deliberated for five whole days, which generated a lot of tension within the general public. They came back with two guilty charges, and Weinstein was sentenced to 23 years in prison.

#4: Johnny Depp & Amber Heard


You couldn’t go anywhere in the spring of 2022 without hearing about Johnny Depp and Amber Heard. Heard has accused Depp of mistreating her during their years-long relationship. Depp defended his reputation and sued Heard after she wrote a defamatory op-ed in The Washington Post. He also claimed that it was Heard who was violent towards him, not the other way around. The resulting trial became a national sensation, with many clips from the livestream going viral on social media. These clips saw millions of views and generated countless memes. It’s been more of a circus than a legal trial, demonstrating how social media has become part of news and information dissemination in this day and age.

#3: The Michael Jackson “Media Circus”


After years of rumors, Michael Jackson was finally taken to court. 2005 saw The People of the State of California v. Michael Joe Jackson, where Jackson faces several charges involving a minor. The trial spanned four months and spawned a media circus that saw countless news outlets depicting Jackson in a negative manner. In fact, journalists criticized the media’s reaction to the trial, calling their coverage “shameful” and inaccurate. The trial also saw the appearance of many notable celebrities, including Chris Tucker, Jay Leno, and Macaulay Culkin - all of whom defended Jackson. In the end, Jackson was found innocent and acquitted of all charges.

#2: Bill Cosby Ruins a Stellar Reputation

2017 & 2018

For decades, Bill Cosby was regarded as a national icon. That all changed around 2014, when comedian Hannibal Buress alluded to how harmful and dangerous he was while on stage. Dozens of women came forward claiming that Cosby had attacked them in some way, and it all led to a legal battle with Andrea Constand. A majority of the cases - other than Constand’s - fell outside the statute of limitations, protecting Cosby from legal repercussions. The trial that resulted following the unsealing of the 2005 deposition in Andrea Constand v. William H. Cosby, Jr. was extensively covered in the media. Following a 2017 mistrial and a 2018 second trial, Cosby’s reputation was permanently tarnished. He was found guilty on three counts and given a three to ten year prison sentence. However, this was overturned in June 2021, as Cosby’s amendment rights had reportedly been violated. He was freed after less than three years behind bars.

#1: O. J. Simpson Generates the Trial of the Century


There’s simply no arguing it - the most sensational celebrity trial of all time belongs to O.J. Simpson. Before the trial, Simpson was regarded as a stellar football player who had long played for the Buffalo Bills. After, he was known solely for the trial, so monumental was its importance to pop culture. This trial was everywhere at the time and was extensively covered in the media. The nation tuned in to watch like it was an episode of “Game of Thrones.” It was filled with iconic twists and turns, memorable moments that live in infamy, and perhaps the most controversial outcome in recent court history. There has never been a public trial quite like it.