The 15 biggest celebrity scandals of the ’90s

Prince Charles and Princess Diana had a tumultuous relationship.

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Prince Charles and Princess Diana had a tumultuous relationship.
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Bob Thomas/Popperfoto/Getty Images

The ’90s were a different time – the fashion was iconic, people weren’t glued to their phones, and progress toward peace in places like Israel and Northern Ireland seemed to finally be getting made.

The decade, of course, was not without its celebrity scandals, ranging from the relationship between Princess Diana and Prince Charles to LGBTQ+ icon Ellen DeGeneres‘ coming out.

Keep scrolling to see 15 celebrity scandals of the ’90s we’ll never forget.


The trial of OJ Simpson was the most talked about event of 1995, lasting from January to October.

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Defendant OJ Simpson wearing the blood-stained gloves found by Los Angeles Police and entered into evidence in Simpson’s murder trial.
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Reuters

Almost 25 years later, the 1994 murders of Nicole Brown Simpson and her friend Ron Goldman are still hotly debated. At the center of the controversy was Brown Simpson’s then-husband, pro-football player and generally beloved star OJ Simpson.

Between the car chase in the white Bronco, the media scrutiny on everyone involved, and the tense situation simmering in Los Angeles after the Rodney King riots (riots that broke out after four police officers were acquitted on charges of using excessive force against King, a black man), it was the perfect storm for a scandal.

Simpson was acquitted of the murders after a 10-month trial, though he was found financially liable in civil court. He maintains his innocence, though he did write a much-maligned book, “If I Did It,” detailing how he would have done it.


Everyone had their own opinions on the Bill Clinton and Monica Lewinsky scandal, which culminated in an impeachment in 1999.

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A photograph showing former White House intern Monica Lewinsky meeting President Bill Clinton at a White House function.
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Getty Images / Handout

The 1999 impeachment made Clinton the second president ever to be impeached, after Andrew Johnson in 1868 (Nixon resigned before he could get impeached). While he was acquitted of all charges, it remains a stain on his presidency, and until recently, was one of the biggest political scandals of all time.

The conflict revolved around a sexual relationship Clinton had with former White House intern Monica Lewinsky in 1995, and whether or not he lied under oath about it.

Some of the key moments and phrases from the ensuing scandal are still part of our cultural lexicon today, like the president’s iconic declaration, “I did not have sexual relations with that woman,” the infamous dress that Lewinsky wore, and Lewinsky’s name in general. She’s been mentioned in over 100 rap songs, according to The Cut.


The relationship between Princess Diana, Prince Charles, Camilla Parker-Bowles, and James Gilbey fascinated the world in the ’90s.

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Princess Diana.
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Bettmann/Getty Images

Not in a few decades had we seen this amount of royal drama. The fact that Prince Charles had an affair while married to Diana, one of the most beloved royals of all time, did not bode well in the world’s eyes.

It seemed like every day there was a new salacious piece of gossip, from Princess Diana confronting Camilla at a birthday party to Prince Charles getting caught on tape wishing he could be Camilla’s tampon to “Squidgygate.”

The pair eventually divorced. Diana was tragically killed in a car crash in 1997, leaving behind her two sons Prince William and Prince Harry. Prince Charles and Camilla are now married.


Woody Allen admitted he was dating his unofficial former stepdaughter in 1992, amid accusations of sexual assault. The two were married in 1997.

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Woody Allen with Soon-Yi Previn at a New York Knicks game.
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John Roca, John/NY Daily News via Getty Images

The dissolution of the relationship between Allen and longtime partner Mia Farrow was spurred by Farrow discovering nude photos of her adopted daughter Previn among Allen’s possessions in 1992.

While Previn wasn’t legally or biologically connected to Allen, the optics are still not the greatest. As Ronan Farrow puts it, “He’s my father married to my sister. That makes me his son and his brother-in-law.”

Allen’s daughter Dylan Farrow has also accused her father of sexually abusing her when she was seven years old. He was never formally charged and Allen maintains his innocence, but his daughter stands by her story.


The first Michael Jackson investigation began in 1993, after the pop star was accused of molesting 13-year-old Jordan Chandler.

Jordan Chandler was the first young boy to accuse Jackson of inappropriate behavior in 1993.

Chandler told a psychiatrist about “incidents of kissing, masturbation, and oral sex,” according to Rolling Stone. His father, Evan, was in the middle of a custody dispute with Jordan’s mother and his ex-wife.

After an investigation, a strip-search of Jackson, interviews, and the testimony of Brett Barnes and Wade Robson (who would later recant this story in 2019’s “Leaving Neverland“), the singer wasn’t charged with any crimes, and he settled out of court with the Chandlers.

Accusations about Jackson’s behavior with young boys would continue for many decades.


Robert Downey Jr. was on a downward spiral, including getting arrested while driving naked.

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Robert Downey Jr. is taken into custody after a judge orders him to be taken to jail.
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John T. Barr/Getty Images

In 1996, Downey was arrested after wandering into a neighbor’s home, most likely thinking it was his own, and climbing into bed and falling asleep. That year he had also been arrested for driving naked and under the influence with a gun in the car, and for possession of drugs like heroin and cocaine.

At a 1999 trial, he heartbreakingly explained his addiction by telling the judge, “It’s like I’ve got a shotgun in my mouth, my finger on the trigger and I like the taste of gun metal.” He had attempted six different drug treatment programs before he was sentenced to three years in prison.

His addiction continued until 2003 when he met his future wife, Susan. Downey credits her with turning his life around. He’s now the linchpin of a multi-billion-dollar movie franchise.


Hugh Grant was caught soliciting a sex worker while dating Elizabeth Hurley in 1995.

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Grant and Hurley.
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Albert Ortega/Getty Images

Grant was picked up by the Los Angeles Police Department after paying a sex worker, Divine Brown, $60 to perform oral sex on him.

Hurley has a sense of humor about the whole thing. On her show “The Royals,” her character even hires an escort who goes by the name of “Huge Grant.”

Read more: 21 celebrities who have been caught in cheating scandals


Julia Roberts became a runaway bride in real life after ditching her planned wedding to Kiefer Sutherland in order to run away to Ireland with the groom’s friend, Jason Patric.

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Sutherland and Roberts in 1990, and Patric and Roberts just two years later.
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Ron Galella, Ltd./Ron Galella Collection via Getty Images and Steve Granitz Archive/WireImage via Getty Images

It’s hard to recall now, but Roberts was something of a wild child in her youth, with a penchant for dating co-stars. She was engaged to “Steel Magnolias” co-star Dylan McDermott when she starred in “Flatliners,” where she met Sutherland. The two quickly began dating and got engaged.

The wedding was set for June 1991 but was abruptly called off by Roberts. The venue was prepared and Sutherland’s Montana home was set for the honeymoon, but Roberts ultimately chose not to go through with it.

A last-minute cancellation and break-up on its own is scandalous, but in the coming days, the story got even wilder. Roberts was soon spotted on a flight to Ireland with none other than Jason Patric, Sutherland’s “Lost Boys” co-star. The two dated for a few months but were over by 1992.


Ellen DeGeneres’ show was canceled after her character (and she in real life) came out as gay.

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“The Puppy Episode” with DeGeneres and Laura Dern aired in 1997.
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ABC Photo Archives/ABC via Getty Images

DeGeneres was the star of her own sitcom, aptly titled “Ellen,” for five seasons. The sitcom might have become another forgotten show of the ’90s if not for one episode called “The Puppy Episode,” which aired in 1997. In it, DeGeneres’ character came out as gay. It was the first time someone on a major sitcom had done so.

Only two weeks prior, DeGeneres came out in real life on the cover of TIME, with the now-famous headline, “Yep, I’m Gay.”

Both revelations caused her show to lose sponsorships, the network chose to air episodes with a parental advisory notice at the top, and eventually, viewers didn’t like the new serious tone of the show. Just one season after she and her character came out, “Ellen” was canceled.

DeGeneres has, of course, bounced back. Today, DeGeneres just extended her popular talk show “The Ellen DeGeneres Show” to continue for another three years.


Coming in right under the wire is the December 1999 club shooting involving Diddy and then-girlfriend Jennifer Lopez, who fled the scene of the crime.

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Lopez and Diddy.
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Kevin Mazur Archive 1/WireImage via Getty Images

In December 1999, Lopez and Diddy were at a New York City club celebrating the release of Diddy’s protégé Shyne’s album when some jostling took place between Diddy and a club patron named Matthew Allen. A fight broke out, and shots were fired at the ceiling. Three people were injured, according to New York Magazine.

The two were pulled over after they fled the scene and found with a stolen gun in their car. While the two were eventually cleared of any wrongdoing, the New York Daily News put it best calling Lopez’s 14 hours in jail, “Her Night in Hell.” The situation was so traumatic that it caused Diddy, then called Puff Daddy, to change his name to P Diddy.


Mike Tyson bit off a piece of Evander Holyfield’s ear during a boxing match.

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Mike Tyson stands in the ring during the fight with Evander Holyfield.
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Sport/Getty Images

Holyfield and Tyson were two of the biggest names in heavyweight boxing in the ’90s. Everyone knew that their fight was sure to be brutal, but no one could have anticipated Tyson getting so riled up that he would literally bite off a piece of Holyfield’s ear.

People forget that Tyson actually bit both of Holyfield’s ears. During the 1997 match, Holyfield unintentionally, according to the referee, headbutted Tyson, and Tyson responded by biting Holyfield’s ear. The match continued, and when Tyson was headbutted again, he bit Holyfield’s other ear.

The fight ended right there, Holyfield was rushed to the hospital and underwent surgery, and Tyson was fined $3 million.


Sinead O’Connor angered millions during her performance on “Saturday Night Live” in which she tore up a photo of the Pope on live TV.

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Singer Sinead O’Connor rips up a picture of Pope John Paul II on October 3, 1992, on “Saturday Night Live.”
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Yvonne Hemsey/Getty Images

During O’Connor’s 1992 performance on “Saturday Night Live,” the “Nothing Compares 2 U” singer chose to take the Catholic church head-on. Years before many in the church acknowledged the rampant sexual abuse problems within the institution, O’Connor sang a cover of Bob Marley’s “War,” held up a photo of Pope John Paul II, ripped it up, and proclaimed, “fight the real enemy.”

The move almost ended her career and earned her a lot of negative press, but she’s said that she has no regrets about the stunt.


Lisa “Left Eye” Lopes of TLC burned down her boyfriend’s house in 1994.

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Lisa “Left Eye” Lopes at the 1999 Source Hip Hop Awards at the Pantages Theater on August 18, 1999.
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SGranitz/WireImage via Getty Images

Lopes burned down her NFL-player boyfriend Andre Rison’s house after she was upset he neglected to buy her a pair of sneakers, according to Paper Magazine. She proceeded to light a piece of cardboard (or sneakers, depending on the source) on fire in the bathtub, and let the house burn down. She also smashed some of his cars.

Lopes turned herself into the authorities and was fined $10,000 and sentenced to five years probation. The two got back together and were planning on getting married until her untimely death in 2002.


Pamela Anderson and Tommy Lee’s sex tape was stolen and leaked in 1995.

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Anderson and Lee.
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Ted Soqui/Sygma via Getty Images

You may remember the iCloud hacks of 2014 in which hundreds of private celebrities’ photos were exposed to the world. That wasn’t the first time something like this happened to a celebrity – one of the very first instances of private footage getting leaked was back in 1995.

Pamela Anderson and Tommy Lee, who famously got married after knowing each other for 96 hours, were the victims of a break-in by a disgruntled worker named Rand Gauthier.

The couple didn’t even realize they were victims of a burglary until months later, when the tape had already been making the rounds on the early days of the internet.


Pee-wee Herman, aka Paul Reubens, plead no contest after he was arrested on charges of exposing himself in a movie theater in 1991.

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Reubens.
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The LIFE Picture Collection/Getty Images

At the time, Pee-wee was an iconic character for kids with his CBS show “Pee-wee’s Playhouse” and his two movies, “Pee-wee’s Big Adventure” and “Big Top Pee-wee.”

But he got himself into a bit of trouble when he was arrested on charges of “exposure of a sexual organ” after reportedly exposing himself at a Florida adult movie theater. The arrest was detrimental to his career and his status as a role model for kids.

Reubens eventually pled no contest to the charges and was required to film two public service announcements.