The Most Talked About Scandals To Rock Hollywood the Past 30 Years

Some celebrity mishaps are so mind-blowing they become embedded into the fabric of our own stories and the past three decades have given us more than a few. Relive each satisfyingly juicy detail.

By Sarah Grossbart Jun 22, 2020 7:00 AMTags
The Most Talked About Scandals To Rock Hollywood the Past 30 YearsGetty Images; X17; Melissa Herwitt/E! Illustration

This June, E! turns 30! To celebrate we're looking back at the most monumental moments in pop culture.

Even before the events of the past few weeks and months shifted our perspective on pretty much everything, what does and doesn't constitute a scandal has always been awfully subjective. One person's OMG is another's half-hearted shrug and all. 

And to be fair, Hollywood's had more than a handful that run the gamut from garden-variety (think a solid early 2000s Hilary Duff-Aaron Carter-Lindsay Lohan love triangle or a surprising celeb split á la Blake Shelton and Miranda Lambert) to mildly shocking (Ariana Grande's #donutgate, any breakup that can be attributed, at least in part, to the nanny) to the type of wrongdoing that involves a potential jail sentence. 

Watch: 5 Biggest Scandals of 2019 - Just the Sip

And while those are the ones that garner the most attention (see: Cosby, Bill, Weinstein, Harvey), a situation doesn't have to involve a courtroom to get people talking as evidenced by how many fans weighed in on Kanye West, Kim Kardashian and Taylor Swift's salacioussssssss feud. 

Bottom line: we all love a juicy controversy—the fights, the infidelity, the inevitable missteps that happen when your life plays out on the biggest stage. It affords us a chance to dissect every detail, hash it out with friends and share our opinion with whomever on the Internet deigns to listen. 

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And the truly groundbreaking ones become embedded into the fabric of our own stories. Who among us (that was of a certain age in the 90s, that is) can't remember where they were when they heard about O.J. Simpson's slow-moving chase taking over L.A.'s freeways or waking up that morning in 2007 to discover how truly wild Britney Spears' previous evening had been? 

There are some celebrity mishaps so mind-blowing, so preposterous, so straight-up fascinating that we simply can't pass up an opportunity to talk about and obsess over each jaw-dropping detail. And the past three decades have delivered more than a few. Pour yourself a piping hot cup of tea and relive all the insanity.  

O.J. Simpson Is Acquitted

For those who had come of age by 1995, that year was all about watching the beloved NFL running back stand trial for the gruesome murder of his estranged wife Nicole Brown Simpson and her friend Ron Goldman a year earlier. Even '80s babies can recall the highlights: the slow-moving white Bronco, Marcia Clark's unnecessarily dissected hairstyles and the fact that, as defense attorney Johnnie Cochran bellowed, the crime scene glove didn't fit, leaving a jury of the athlete's peers to decide they must acquit. 

A quarter century later you'd be hard-pressed to find someone who doesn't hold a strong opinion about Simpson's guilt or innocence. One of the most talked about scandals, not just in Hollywood, where it was broken down in FX's 10-part 2016 anthology, but of all time anywhere it's a prime example of our obsession with true crime as well as a fascinating case study in race relations that remains all too relevant today.  

Michael Jackson Goes to Trial

Perhaps even more of a circus than the nine-month Simpson case, the King of Pop's 2005 trial saw him facing the equally serious charges of child molestation. Playing to the crowd, at one point even hopping atop a car to wave to fans, he was eventually found not guilty, but his reputation never fully rebounded as he fell from music superstardom to not-all-that-funny punchline. A decade after his untimely 2009 death (which, in itself, led to a court case), he was tried once again in the court of public opinion thanks to the Wade Robson and James Safechuck-led documentary Leaving Neverland, repeatedly denounced by his estate.  

Bill Clinton Has an "Improper" Relationship

Maybe if the then-president hadn't fibbed about having "sexual relations with that woman," we all could have been spared the 1998 grand jury investigation into his dalliance with White House intern Monica Lewinsky and the subsequent impeachment trial. Instead, it's all seared into our memories: Ken Starr's report, the stained blue dress and how the bulk of the ire was somehow directed toward the women involved. Having withstood the endless sexist attacks, Lewinsky is now an advocate for victims of bullying, while Hillary Clinton, maligned for choosing to remain married, came thisclose to her own stint in the Oval Office. 

The Rise and Fall of Brangelina

The beginning was shocking. Those April 2005 photos on that Kenyan beach confirming what had been gossiped about since Brad Pitt's big split from wife Jennifer Aniston three months earlier—he was, in fact, dating his Mr. and Mrs. Smith costar Angelina Jolie. For months, each new development in their romance seemed more jaw-dropping than the next: that W magazine "Domestic Bliss" shoot that left Aniston declaring her ex was missing a "sensitivity chip", Jolie's January 2006 pregnancy announcement, the Team Jen vs .Team Angelina of it all.

And just when we'd all gotten used to two of the world's sexiest movie stars being a happily peripatetic family of six, had almost forgotten their less-than-savory origins, it was suddenly all over, the once madly in love pair leaving a trail of rumors, custody battles and tales of throwdowns at 35,000 feet in their wake. Like we said, shocking.

Lance's Legacy Comes Crashing Down

At one point in the mid-2000s it was rare to spot a wrist not laden with one of those yellow rubber Livestrong bracelets. That's how much the nation was rooting for champion cyclist and cancer survivor Lance Armstrong. Then, with one 2012 report, he crashed hard, the U.S. Anti-Doping Agency declaring him the ringleader of "the most sophisticated, professionalized and successful doping program that sport has ever seen". After months of public denials, he copped to the blood-doping, was stripped of his seven Tour de France titles, banned from the sport, ordered to repay millions in prize money and endorsements and even endured a public tongue lashing from Oprah Winfrey. Now, you can relive the particulars with ESPN's new docuseries Lance. It's quite the ride. 

Hugh Grant Has a Divine Intervention

It's a testament to just how charming the forever fumbling British actor is that he escaped from this one relatively unscathed. After the Four Weddings and a Funeral star was arrested for picking up prostitute Divine Brown that summer day in 1995, his sheepish mug shot plastered across the nightly news, he reported to The Tonight Show With Jay Leno and offered a full mea culpa. Even then-girlfriend Elizabeth Hurley forgave his misdeed, the pair remaining friends to this day. "I was just an idiot," he reflected to People in 2018. "I didn't try to say, 'I've got this psychological problem.' I just said, 'I did it.'"

Winona Snags a Discount

Coming off a decade's worth of hits (Beetlejuice, Heathers, Girl, Interrupted) one wouldn't think '90s It star Winona Ryder required help obtaining designer wares. And yet there she was being busted at a Beverly Hills Saks Fifth Avenue for shoplifting some $5,500 of goods in December 2001. Entirely wild at the time, we'd have to agree with her 2016 assertion that it "wasn't like the crime of the century!" Instead, after a six-day trial and a guilty verdict for grand theft and vandalism, it provided the impetus for Ryder's temporary escape from Hollywood. "Psychologically, I must have been at a place where I just wanted to stop. I won't get into what happened, but it wasn't what people think," the actress, now scaring up accolades on Netflix's Stranger Things told Porter Magazine. "It allowed me time that I really needed."

Britney Stages a Comeback

Ever had a year so bad that it became a popular meme? That was Britney Spears' 2007. Her triumph over a particularly traumatic annus horribilus that saw the newly divorced pop star and mom of two check in and out of rehab, shave her head in full view of paparazzi cameras, wield an umbrella against a pack of photographers and end up on an involuntary psychiatric hold and under the guardianship of her father serves as inspiration for strugglers everywhere. As in, if Britney can get through 2007...

Because now, Brit is definitely back y'all. Though still under her dad's conservatorship, she's made the full transition from tragic cautionary tale to biggest pop star of our generation with multiple Vegas residencies, a thriving personal life and, against all odds, a coparenting relationship with ex Kevin Federline

Pee-Wee Goes to Jail

The term Pee-wee's Playhouse gained a new, and altogether more disturbing, meaning when actor Paul Reubens was arrested by police, who said he was spotted masturbating at a Florida porn theater in 1991. Pleading no contest to indecent exposure in a deal to get the charge dropped from his record, there was little he could do to repair the hit to his reputation as the red bowtie-wearing oddball host of Saturday morning TV. That is, until 2016 when Netflix cashed in on '80s nostalgia with Pee-wee's Big Holiday and inspired Reubens to consider other avenues for his persona. "People have argued I've done everything consciously or unconsciously to destroy [the character]," he told The Hollywood Reporter earlier this year. "But it's the brand that won't die. It's still around."

Kristen and Rob’s Fairytale Unravels

Ah, young love. Perhaps it was unfair to assume Robert Pattinson and Kristen Stewart would remain as eternally entwined as Edward Cullen and Bella Swan. But that didn't make the news of her 2012 dalliance with married Snow White and the Huntsman director Rupert Sanders any less startling, particularly when the report came with photographic evidence. (Though, as she would make clear in a 2019 interview with Howard Stern the affair didn't extend beyond kissing and some fairly PG cuddling: "I did not f--k him.") Following the then-22-year-old's apology, the Twilight couple formerly known as Robsten attempted a sequel, but it became clear their love story was best reserved for the silver screen. 

Tiger Hits the Rough

Few facades crumbled quite as fast or as spectacularly as Tiger Woods'. A child golf phenom turned beloved sports icon and entirely likable father of two, he was four victories away from besting Jack Nicklaus' record of 18 major title wins in 2009 when news emerged over Thanksgiving weekend that he'd crashed his Escalade into a tree outside the Florida mansion he shared with wife Elin Nordegren. She's dismissed the popular narration that she was in pursuit with one of his clubs, but regardless his web of deceit had caught up. Within weeks, 14 lovers had come forward with receipts (and, in one case, a saved voicemail) painting a picture of an arrogant serial philanderer. 

A public apology and 45 days in a treatment facility couldn't save his five-year marriage, but following several injury-plagued seasons, he got back in the swing of things professionally, nabbing his fifth Masters' green jacket in 2019. 

S--t Goes Down in an Elevator

Cameras are strictly forboden at Anna Wintour's annual Met Gala, but even the most star-studded snap couldn't have topped the footage that was released from Jay-Z, Beyoncé and sister Solange's post-afterparty elevator ride at NYC's Standard Hotel. Though the 2014 surveillance video was rather explicit, showing Solange more or less losing her s--t on her brother-in-law as Bey stood motionless, and rumors abound (he'd been flirtatious with designer Rachel Roy; they'd set up the whole thing to promote their forthcoming tour), for awhile it seemed we'd never truly know what went down in that elevator. 

Then Queen B dropped Lemonade and suddenly everyone was speculating about Becky with the good hair. Though that particular mystery remains, Jay directly addressed infidelity chatter with his 4:44 disc, making reference to Halle Berry's cheating ex: "You egged Solange on / Knowin' all along / All you had to say you was wrong / You almost went Eric Benét / Let the baddest girl in the world get away". In the end, though, he kept their power couple status and his relationship with Solange intact. "We had one disagreement ever," he said in a 2017 podcast interview. "Before and after, we've been cool."

Janet Jackson Gets Exposed

Before the term "wardrobe malfunction" was synonymous with nip-slip and we all agreed to start tacking "gate" onto anything remotely scurrilous, there was Nipplegate. Looking back, the five-time Grammy winner's decorated right nipple was exposed for precisely 9/16 of a second when 2004 Super Bowl Halftime Show duet partner Justin Timberlake accidentally ripped off more bodice material than originally intended. (In contrast, 15 years later, headliner Adam Levine spent entire songs flashing his plentiful chest tattoos.)

But the fallout was massive: CBS was fined $550,000 by the FCC (a decision ultimately overturned) and, in a head-scratching display of double standards, an apologetic Timberlake was still able to attend CBS' Grammys presentation days later, but Jackson's invite was promptly rescinded. The network's parent company Viacom, meanwhile, had her music scrubbed from MTV, VH1 and their radio stations. As Jackson would tell Oprah Winfrey in 2006, "I think they did put all the emphasis on me, as opposed to us."

Charlie Sheen Starts "Winning!"

For a stretch in 2011 it was pretty much impossible to go anywhere without hearing the Two and a Half Men alum's signature catchphrase. "Winning!" There was also talk of tiger blood, Adonis DNA (which he explained as his reason for not needing Alcoholics Anonymous or other treatment) , a 20-city Torpedo of Truth tour and a whole lotta confusion about what exactly was going on there. TBH, we're still not entirely sure and it's not clear if Sheen is either. "I think it's important that people see that I see and I feel that that was just one crazy chapter," he said on Today later that year, "one weird phase, and that I was this guy before it started and I can be that guy again afterwards."

Chris Brown and Rihanna Take a Bow

Massively talented, attractive, young and in love, the R&B star and the "Umbrella" chanteuse were primed for a long future as one of music's power couples. With five nominations between them, each were set to make waves at the 2009 Grammys with their separate performances. Instead, they were the talk of the night for all the wrong reasons as news spread that a fight between them had become seriously, horrifyingly physical. 

Photos, later leaked by a person Rihanna would describe to Vanity Fair as "a very nasty woman who thought a check was more important than morals," showed the extent of the damage and a police report filled in the rest. Police said Brown had punched Rihanna repeatedly in the face and arm, even biting her ear. Pulling the rented Lamborghini to a stop, he put her in a headlock causing her to slowly lose consciousness. "I went from being on top of the world, No. 1 songs, being kind of like America's sweetheart to being Public Enemy No. 1," Brown recalled years later in his 2017 documentary Chris Brown: Welcome to My Life. "I felt like a f--king monster." The pair attempted to reconnect before accepting their romance was entirely toxic. "I don't hate him," she insisted to Vanity Fair. "I will care about him until the day I die. We're not friends, but it's not like we're enemies."

Milli Vanilli End on a Sour Note

Girl, you know it's true that at one point the German R&B duo of Rob Pilatus and Fab Morvan seemed primed to rule the world of pop music until a record skip during a live performance on MTV exposed the truth: they'd been lip-synching the whole time. "I knew right then and there, it was the beginning of the end for Milli Vanilli," Pilatus told the Los Angeles Times in November 1990. Stripped of their 1990 Best New Artist Grammy, they attempted to prove their singing chops with the 1993 release Rob & Fab, but it sold just 2,000 copies. Pilatus was later found dead of a suspected overdose in a Munich hotel room in April 1998, the night before they were set to tour in support of their comeback disc, Back and In Attack.  

Brittany Murphy's Truly Bizarre Passing

In the 10-plus years since her shocking death, fascination into the why of it all hasn't waned one bit. Drugs? Toxic mold? Poison? Foul play? All were weighed as options in the months and years after the 32-year-old suddenly perished just before Christmas in 2009. The official autopsy labeled the cause as pneumonia, anemia and multiple drug intoxication, but enough truly bizarre twists and turns followed to cause all sorts of reasonable doubt. 

Her seemingly out-of-nowhere marriage to Brit Simon Monjack was considered with suspicion until the writer-director-photographer died from the exact same cause just five months later, the actress' mom Sharon Murphy claiming he'd died of a broken heart. And while the Clueless star's dad Angelo Bertolotti presented a compelling argument about the possibility of heavy metals poisoning before his 2019 death, her mom blocked any chance of exhuming her body until it was too late. Officially, the case is closed, but speculation lives on. 

Jon & Kate Divide

On the 2007 premiere of TLC's Jon & Kate Plus 8, laid-back former I.T. specialist Jon Gosselin and his no-nonsense pediatric nurse wife Kate Gosselin seemed merely unhappy. But as their ratings soared—a record 4.6 million tuned into watch the parents of twins Cady and Mara and sextuplets Collin, Hannah, Alexis, Aaden, Leah and Joel on the 2009 season four finale—their relationship plummeted.

Jon has since claimed their young love was doomed from the start, opining on The Dr. Oz Show in 2019, "I think eventually, because of personality, it would have fizzled out anyway," the end was more of a catastrophic flame out. There were cheating accusations on both sides (Kate had to deny a romance with her salt-and-pepper coiffed bodyguard while Jon entertained increasingly younger suitors), a legal attempt by Jon to block filming, vicious custody battles, unfortunate Ed Hardy apparel and so many tabloid covers that no less than Vanity Fair dubbed them the biggest celebrity story of 2009.

A Housewife Does Time

"Happy wife, happy life." So Joe Giudice declared on that opening season of The Real Housewives of New Jersey in 2009. Turns out, the inverse was true as well. Blaming ignorance about the particulars of his financial dealings, he and bride Teresa Giudice pled guilty to 41 counts of fraud and were dealt back-to-back jail sentences in 2014. With mere months together between the Standing Strong author's 11-month stint and her hubby's more than three-year stay, plus her continued admission of anger towards his massive screw-up, good money was on the parents of four breaking free from their 20-year marriage. When the native of Sala Consilina Italy was deported last year following his jail stint to the country he'd left behind as an infant, they officially said "Ciao!" to their life together.  

Two Words: Bill Cosby

His improper behavior had been discussed for years without any real repercussions save for the five-count civil lawsuit Andrea Constand brought in 2005 (naming 13 other anonymous women in the papers) after a Pennsylvania DA announced they wouldn't move forward with her claims that he'd drugged and sexually assaulted her the previous year. It took a 2014 set from Hannibal Buress, in which the New York comedian called Cosby "a rapist", for his legacy as America's favorite jolly dad to truly be supplanted.

From there any and all childhood illusions were completely shattered as scores of women came forward accusing The Cosby Show head and Jell-O purveyor of sexual assault dating back to the 60s, their stories sharing disturbingly similar details. The statute of limitations having expired on many of the 50-plus accusations it was Constand's once-dismissed claims that finally brought the octogenarian to trial. He was sentenced to three to 10 years in 2018 for sexual assault and, despite a few failed appeals, remains behind bars at a Pennsylvania maximum security prison. 

Also: Harvey Weinstein

Three years after Cosby's comeuppance, the mega-producer's carefully constructed reality unspooled. Act one saw actress Ashley Judd and several other women come forward with sexual misconduct allegations in an October 2017 New York Times article. Act two was an onslaught of names—everyone from Rose McGowan to Rosanna Arquette to Gwyneth Paltrow—sharing their tales of how the Hollywood insider used his considerable weight in the industry to force them into sexual acts, each accusation of rape, assault and indecent exposure as horrifying as the next. Though he held out hope for a redemption arc, the now-single dad of five (ex-wife Georgina Chapman announced their separation in the days after the Times piece) is currently in jail serving a 23-year sentence after a New York jury found him guilty on two counts: rape in the third degree and criminal sexual act in the first degree. 

Taylor Swift Has Bad Blood With Kanye West

Imma finish this list, but we'd be remiss if we didn't mention the ongoing saga that is the ballad of Taylor and Kanye. At odds since he crashed her VMAs party in 2009, they appeared to kiss and makeup in 2015 only for it to devolve into a mess of he said-she said accusations and snake emojis when Kim Kardashian released a clip of their phone conversation about her husband's 2016 single "Famous" and that much-disputed lyric—"I feel like me and Taylor might still have sex/ Why? I made that bitch famous." A handful of revenge songs and one 63-foot inflatable cobra named Karyn later, neither side has truly shaken the feud off. 

Jussie Smollett Gets Attacked, Then Indicted

This one is, admittedly, still a bit of a head-scratcher. In January 2019, the former Empire star claimed he was attacked by two white men in ski masks while leaving a Subway sandwich shop in Chicago. Police announced they were treating the incident as a possible hate crime, but three weeks—and scores of public statements of support—later shifted course, saying they were charging the actor with disorderly conduct for allegedly filing a false police report, a felony charge that could lead to years in prison.

A month later, prosecutors dropped all charges, with Smollett telling reporters, "I've been truthful and consistent on every single level since day one." But this past February, after back-and-forth lawsuits between the actor and the city of Chicago, he was indicted once more, a grand jury charging him with six counts of disorderly conduct for lying to police. Once again, he faces jail time, but regardless of how it all shakes out (he pled not guilty to the new charges), the damage to his reputation—and career—will likely remain. 

Aunt Becky Goes to Jail...Maybe

Okay, technically this one hasn't happened yet, but it could happen if the judge signs off. Little more than a year after Lori Loughlin was implicated in the Varsity Blues college admission scandal alongside some 40 other parents, including Felicity Huffman, she and husband Mossimo Giannulli struck a plea deal. (She pled guilty to one count of conspiracy to commit wire and mail fraud; he pled to one count of conspiracy to commit wire and mail fraud and honest services wire and mail fraud.) Under her agreement (subject to court approval), the embattled former actress, cut from the final season of Fuller House and her Hallmark Channel gigs has agreed to complete a two-month sentence. And everywhere you look someone is offering their take on the whole charade. 

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