The Biggest Scandals of Our Time: A Definitive Guide, From O.J., Monica and Michael Jackson to Brangelina and Britney Spears

We polled our own staff as to what has stayed with them over the years and why, and the wide-ranging results—as well as what we have in common—provided a lot of food for thought

By Natalie Finn Aug 29, 2016 1:00 PMTags
Celebrity ScandalsBauer-Griffin; Getty Images; AP

The Internet being what it now is, society births at least a scandal a day.

The feuds, the rants, the catchy hashtags, all the hacking... Not to mention a social media landscape that has given everyone a voice, some louder than others, and made it possible to unearth past foibles at an alarming clip, so much so that every prominent person's present and past almost seem to be unfolding simultaneously.

But in reality, it's not every day that something occurs that reaches landscape-altering, world-rocking, stay-with-us-forever status—or at least resonates in such a way that, 26 years later, you're psyched to watch it unfold for 10 weeks on FX.

Maybe that's why so many of us relish a juicy scandal—to be scandalized together is to reel together, to agree on something, to be a unified force in the wake of madness, to be brought closer by someone else's screw-up. Which is so much better than being divided by our own screw-ups, right?

And yet, while some scandals are now just built into the fabric of our society, not everyone is affected by the same things in the same way. What caused one person to shrug may have been a rude awakening for another. One's vague memory be another's crystal-clear remembrance of the day the music died. One person's LOL is always another's ghostly-scream emoji.

But there was only one way to find out what has meant what to whom and why, so I asked my co-workers: What do you feel has been the defining celebrity scandal of your lifetime? And on a different note, or the same note, what scandal has resonated the most with you

Here's what they—women and men, in their 20s, 30s and 40s, hailing from all over the United States but now working side by side in the entertainment epicenters of the universe—had to say about the biggest scandals of our time:

Political Scandals


What we think about when we hear the word scandal.

AP Photo/Myung Chun

O.J. Simpson Murder Case

"I remember my 4th grade teacher stopped class to watch the verdict. I didn't really understand what was happening other than that it was huge." —Jean Bentley, Editor, TV

That about sums it up right there. What could have been dismissed as the defining scandal of our parents' time remains, 26 years later, the defining scandal of all of our times, the most-cited occurrence by my colleagues, some of whom weren't even teenagers yet when Simpson was tried and found not guilty of murdering his ex-wife Nicole Brown Simpson and her friend Ron Goldman.

If you were already a grown-up, then you were watching one of the most popular football players of all time crash and burn. If you were 14, you at least remember where you were when the Bronco chase happened and when the verdict was announced. And even if you were only 9, you knew something was amiss in the force. 

In fact, maybe a quarter of a century needed to go by before anyone, kid or adult, could truly process the enormity of Simpson's downfall and the societal context in which it occurred.

Buoyed in some age groups, of course, by the FX anthology The People v. O.J. Simpson: American Crime Story, which is nominated for 22 Emmys, and the positively gripping five-part, 7 1/2-hour documentary O.J: Made in America, the case remains a source of endless fascination. Variably considered one of the greatest-ever miscarriages of justice, a resounding verdict on race relations in Los Angeles and beyond, a victory for a historically oppressed segment of the population and a haunting reminder of how easily a seemingly airtight ship can spring a leak and sink like a stone, the O.J. Simpson case is still the case study of celebrity-crime hysteria.

The Downfall of O.J. Simpson: Why We'll Never Stop Talking About the Murder Trial That Changed Media Culture Forever
Justin Sullivan/Pool/Wireimage

Michael Jackson Brought to Trial on Molestation Charges

"I remember the clothes he wore. The waving on the car. Everything!" —Lily Harrison, Senior Editor 

Memo to Hollywood: When the 25th anniversary of this "not guilty" verdict rolls around, please don't make a limited series out of it. While every bit as surreal as the O.J. trial, if not more so, the disturbing allegations against Jackson (Thriller on vinyl was the go-to gift among my preschool set in 1984, every pile of presents at a birthday party boasting at least one large, flat wrapped square) forever made him a punchline even if there was really nothing funny about any of it. 

The trial, at the end of which Jackson was acquitted on all charges yet branded for the short rest of his life a weirdo, was a true circus. Jackson even attempted to be the ringmaster, dutifully greeting the curious hordes that gathered outside the Santa Barbara courthouse daily. Inarguably a musical genius but still a tragic figure, his musical legacy wasn't restored until after his untimely death at 50 in 2009. And even then, a trial ensued.

CNN screen grab

President Bill Clinton Has an "Improper Physical Relationship" With Monica Lewinsky

So the commander in chief finally admitted to a grand jury in 1998, leading to his impeachment for lying during a previous deposition (and, unofficially, for lying to the world about not having "sexual relations with that woman").

The stained blue dress, the Starr report, cigars...Never before or since have politics been so ripe for DNA testing.

For those of us in college at the time, there was no better crash course in political science, diplomacy, partisan animosity and prurient dorm humor. And still, nothing says more about the multi-headed monster of sexism than the horrible things said about Lewinsky, who today is an advocate for victims of bullying, and the judgment passed on Hillary Clinton for remaining married and supposedly blaming the other woman. (You know, because everyone else in Hillary's position would have gotten divorced and stuck up for the other woman.)

Postscript: Ken Starr, who investigated the Clintons, resigned as chancellor of Baylor University in June in the wake of a controversy regarding the handling of sexual assault allegations on campus.

20th Century Fox

Brad Pitt and Angelina Jolie Become a Couple

"Brad Pitt-Angelina Jolie-Jennifer Aniston—in terms of A-list sensationalism at its best—takes the cake for all-time greatest love triangle." —Alli Rosenbloom, Senior Reporter

"I'll never forget those photos of Jen and Brad on the beach together, only to be followed by a divorce announcement a few days later. 2005 was a bad year, and honestly, I'm not sure anyone my age is over it. #TeamJenForever." —Francesca Bacardi, News Writer-Editor

And this is why you poll the crowd. While it's on the opposite end of the spectrum of the other defining scandals, the rise of Brangelina—aka Brad's split from Jennifer Aniston after he and Angelina met and fell in love on the set of Mr. and Mrs. Smith—remains a touchstone for almost as many people as said the same about O.J.

It didn't initially occur to me because, at this point, we're just so used to Brad and Angelina being together. But in retrospect... that was huge. Not only did one of the most famous couples in the world have to break up for it to happen, but it was almost too much to see the reigning sexiest movie stars on the planet as a real-life couple. And then those movie stars started living happily ever after together, like, immediately and the two actresses in the equation were pitted against each other for years.

What a time to be alive.

Tim Graham/Getty Images

More of the Most Shocking Scandals

• The death of Princess Diana: The "People's Princess," by then divorced from Prince Charles, was killed along with boyfriend Dodi Fayed in a high-speed car crash in Paris in 1997. Their driver, later determined to have been under the influence, was widely reported to have been fleeing paparazzi—an ugly mark on the profession even though the driver was ultimately found to be at fault. But the crash was probed like the Kennedy assassination, with an inquest taking place in 2004 and continuing in 2007, while the 2006 film The Queen dramatized the royal family's handling of Diana's death.

• Champion cyclist, cancer survivor and wristbands-for-a-cause unleasher Lance Armstrong turning out to be a blood-doping liar: The Livestrong Foundation founder was ultimately stripped of his seven Tour de France titles and ordered to pay back millions of dollars in prize money and endorsements. Not to mention there was Oprah Winfrey's wrath to face.

Woody Allen leaving longtime partner Mia Farrow for her adopted daughter, Soon-Yi Previn in 1992: Putting out at least one movie a year, some of them really good, has proved an excellent distraction from this stomach-churning bullet point in Hollywood relationship history. Now married for 19 years, however, Woody and Soon-Yi have two adopted children and at least she's in her 40s now. But the renewed accusation from biological daughter Dylan Farrow that Allen sexually abused her when she was little (he has expressly denied it) is ensuring that the now 80-year-old filmmaker's legacy will not be left unscathed.

Celebrity Sex Addicts

• Hugh Grant is arrested with prostitute Divine Brown: "I was really young then so I'm pretty sure that was the first time I ever heard the word 'prostitute.' I'm not even sure I knew what it all meant except that his girlfriend in the safety pin dress was not going to be happy." —Holly Passalaqua, Senior Associate, News Operations

Grant mused on The Howard Stern Show recently that it wouldn't be much of one, but as a 14-year-old I was so bummed when the next I saw of the charming star of Four Weddings and a Funeral was his mug shot on the 10 o'clock news. And Grant apologizing on The Tonight Show With Jay Lenoand turning Leno into the late-night ratings leader for pretty much the rest of his entire run—remains one of the most memorable (and successful) mea culpas ever.

I'm also willing to bet Grant's misstep was the first dance with celebrity forgiveness for a lot of us, whether we realized it at the time or not...


The one that answered both questions for so many.

The Fall and Rise of Britney Spears

"The paparazzi just wouldn't leave her alone and I remember thinking, 'What they're doing to her is absolutely horrible. Just let her live.'" —Francesca Bacardi

"I couldn't believe we were watching the biggest pop star of our generation crumbling." —Diana Marti, Senior Writer-Producer, TLMD Digital

It's so much better to be able to talk about Britney and how her life started unraveling in 2007 now, just hours removed from her triumphant return to the MTV Video Music Awards as a performer. Because otherwise it would have been too sad to think about how the mother of two started behaving erratically, shaving her head in full view of the paparazzi on one memorable night, and ended up on a psychiatric hold and then under the guardianship of her father.

She does remain in a conservatorship (how many of us learned that word for the first time thanks to Britney?)—we like to think that Dad managing her business affairs all these years has worked in her favor—but the extent of her comeback from the brink of becoming just another cautionary tale of celebrity gone wrong is remarkable.

But since it's been a good 11 years now since Britney and Kevin: Chaotic and people still feel the need to root for Spears, as though she still needs the support of each and every one of us to stay afloat, that must be the reason why Britney Spears' rocky road is often both the first thing to pop into people's heads when they hear the word "scandal" and the story that we're all still following as if it were yesterday.

Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images
Britney Spears' Carpool Karaoke With James Corden Is Filled With Dick Jokes, High Notes & Schoolgirl Uniforms


This is where the answers started to run the gamut.

Pee-wee Herman Gets Busted in a Movie Theater

Even though Paul Reubens hadn't made a new Pee-wee's Playhouse in over a year, his arrest in 1991 after, according to police, he was spotted masturbating at a Florida porn theater (controversy also ensued when it appeared that Sarasota police were targeting adult theaters), instantly made him persona non grata on morning TV. He pleaded no contest to indecent exposure in a deal to get the charge dropped from his record, but it took almost 15 years for nostalgic love of Pee-wee to get the character another starring role on screen (via Netflix earlier this year in Pee-wee's Big Holiday). 

For those of us who spent so much of our childhood watching Pee-wee on Saturday mornings...luckily we may have been still too young at the time to truly, er, grasp what had happened.

Biggest Sports Scandals
Harry How/Getty Images

When Celebrities Cheat

We've seen more than a few cheating scandals in our time, and whether they involve many partners, one partner, other actors, directors or nannies, they tend to leave a mark.

Thinking about the ones our staff mentioned, Tiger Woods alone remains truly shocking to me. He was one of the most famous athletes in the world, a childhood phenom who had lived up to his potential, an international sports icon, a man of mixed race on top of a historically white man's game. He seemed destined to break Jack Nicklaus' record of 18 major title wins, no problem, and was only four away in 2009 when...

Let's just say, is there a sports psychologist in the world who thinks that Tiger's major drought of now eight years is only related to injuries, and has nothing to do with him being unmasked as a serial cheater on now ex-wife Elin Nordegren, the mother of his two kids?

Other eye-openers among our set: 

Famous Athletes Caught Cheating

Gwen Stefani divorcing Gavin Rossdale amid rumors he had a years-long affair with their nanny—even Gwen has said that whatever happened is "a really good, juicy story" that's not to be believed.

• Rumors that Ben Affleck and Jennifer Garner's split was hastened by his alleged relationship with their nanny, who was a paparazzi darling for a few weeks last year before squirreling herself away for the winter.

Deana Newcomb/Imprint Entertainment/Entertainment Pictures via ZUMA Press

Kristen Stewart caught stepping out on real and Twilight love Robert Pattinson with her Snow White and the Huntsman director Rupert Sanders. Robsten actually managed to reconcile for a bit (both are in much happier and realer-seeming relationships now) but Sanders' wife, Liberty Ross, dumped his ass. She's now remarried to record mogul Jimmy Iovine.

Beyonce + Solange + Jay Z + Elevator = Lemonade?

"That's when I realized no one's life is perfect, even Queen B's, and it always makes me wonder what else is hiding behind her picture-perfect life and beyond Lemonade." —Diana Marti

When Solange unleashed her fists of fury on her brother-in-law in a hotel elevator while—as the story has historically been told—sticking up for her sister after the 2014 Met Gala, the shock to the system of those who took Bey and Jay's union as gospel was real. To this day, the common dream among humans is to have been a fly on the wall of that elevator. But Beyoncé's tactically brilliant 2016 album-short film extravaganza known as Lemonade managed to make us all feel closer to her than ever and also very far away, as the realization dawned that this is their narrative and we're just drinking it in. 

Wild Reality TV Scandals
Kevin Mazur/

Nipple-Gate 2004

"The thought of 'wardrobe malfunction' not being a part of our vocabulary until this moment is unbelievable. Whether we want to admit it or not, there may never be a Super Bowl Halftime Show as buzz-worthy as this.'s safe to say anything can happen on live TV." —Mike Vulpo, Writer

Justin Timberlake ripping Janet Jackson's bodice and exposing her decorated right nipple for barely a second during the 2004 Super Bowl Halftime Show resulted in thousands of dollars in fines for CBS (overturned on appeal), a ridiculous double standard in which Jackson's invite to the Grammys was rescinded by the network and Timberlake's wasn't, and the awful trend of tacking -gate onto a word to signify anything remotely scandalous.

Watergate was the name of a hotel, dammit!

Art Reflects Life

Remember that time when future Runaway Bride star Julia Roberts just about left Kiefer Sutherland at the altar, calling the whole thing off three days before their wedding? Well, trust us, it was on the cover of every magazine in 1991.

Beauty Pageant Scandals

Feuds, Wonderful Feuds

• The butting of heads on The View is forever, but the gold standard remains Rosie O'Donnell vs. Elisabeth Hasselbeck.

"The anger, hostility and awkwardness between these two co-hosts still gives me anxiety." —Mike Vulpo

• Oh, fickle young love. Lindsay Lohan feuding with Hilary Duff after Aaron Carter dated them both at the same time, then getting back with Hilary and totally giving her the run-around? Forget about it...never! 

"That was just my childhood. The fact that Hilary released 'Haters' was just the pristine cherry on top. It was peak, petty celebrity drama in good fun. Well, it probably was only fun for Aaron Carter." —Bobby Caruso, Weekend Social Media Editor

• Taylor Swift's ongoing war of words with Kanye West and, now, Kim Kardashian: Taylor had been on a one-way high road since 2009 but now, thanks to Kim, she's just playing on the same treacherous as everybody else.

The 17 Best (or Worst) Celebrity Apologies: Where Does Jonah Hill Rank?


The omissions are also notable: No mentions of Paris Hilton going to jail, Chris Brown and Rihanna, Charlie SheenBill Cosby, Arnold Schwarzenegger's love child, Tom Cruise diminishing postpartum depression, Lindsay Lohan's revolving door of court and rehab, Robert Downey Jr. falling asleep in someone else's house, Isaiah Washington's firing from Grey's Anatomy, no Deflategate or Doughnut-Gate or Egg-Gate...or anything having to do with Justin Bieber for that matter!

The list goes on. And for whatever reason, these certainly memorable instances didn't rank when it came time to pick the scandals that most popped—in the world and in our own heads. But we could play the "oh yeah, that!" game forever.

Overall the variety of responses—as well as the places where people's memories aligned, with no knowledge of each other's answers—were an intriguing multi-generational mix of blasts from the past and more recent headlines, royalty and athletes, politicians and A-list actors, triumph and tragedy, love gone wrong and, interestingly, love gone right.

Looming over everything, for many, was the "Trial of the Century." The People vs. Michael Jackson took the definitive-scandal cake for others. And then Brangelina came along and stole all the thunder... again.

Celebrity Scandals