Craziest Celebrity Scandal The Year You Were Born

By: Kish
July 22, 2019

So far, the biggest celebrity scandal in 2019 has to be when Jordyn Woods hooked up with Khloe Kardashian’s cheating boyfriend and baby daddy Tristan Thompson. The Kardashians took it in their stride (sort of) and everyone picked their sides, held their own theories on what happened, and hoped for the best. It shook everyone to the core, but before long, another scandal had come along and distracted everyone from the travesty.

That’s because celebrity scandals are a dime a dozen. Stretching all the way back to the ’80s, even before old tweets and Instagram comments were getting people in trouble, stars have had public meltdowns, bitter divorces, jilted one another at the aisle, and assaulted paparazzi. Some have even while wound up dead in the most mysterious circumstances. These moments inspire the weirdest conspiracy theories that end up tangled with the truth. It’s almost hard to keep up.

We’ve seen the mug shots, gossiped about the rumors, and wondered ‘is it really true’ about the wildest scandals, but have you ever considered what was going on the year you were born?

We compiled a timeline of the craziest celebrity scandals the year you were born.


One breakup left us aghast.

It was wild when Kate Moss was caught snorting illicit drugs and the photos were splashed across the front page of London’s Daily Mirror. It was devilishly scandalous when Tom Cruise took to Oprah’s couch only to jump up and down about how much he was in love with Katie Holmes. But Brad Pitt leaving Jennifer Aniston for his on-screen romance from Mr. and Mrs. Smith, Angelina Jolie, takes the cake for 2005 celebrity scandals. When Hollywood’d golden couple split after seven years, everyone’s hearts were broken for them— especially Jennifer.


A very awkward Superbowl performance shocked the world.

Celebrity breakups always define a year, and Ben Affleck’s split from Jennifer Lopez was a big deal. And power couple Victoria and David Beckham held it together despite Rebecca Loos coming out and claiming she was the footballer’s mistress. But the scandal that rocked the world was Janet Jackson and Justin Timberlake’s performance at the Superbowl, where a wardrobe malfunction caused chaos. It’s known today as ‘Nipplegate.’


This was the hottest kiss of the year.

In 2003, the MTV VMAs was home to all the drama. Britney Spears was the princess of pop and was newly single (goodby,e Justin Timberlake!) All this culminated into one of the biggest moments in pop culture history. Following the release of “Toxic”, Britney took to the MTV stage to perform the song alongside Madonna and former foe, Christina Aguilera. Everything was normal until she stopped to make out with Madonna— and everyone lost it!


There were some major breakups this year.

Drew Barrymore divorced Tom Green after being married for less than a year, Nicole Cage and Lis Marie Presley called it quits after 3 months and Justin and Britney ended their iconic relationship. This left hopeless romantic’s head spinning. But the craziest celebrity scandal wasn’t a breakup. Instead, Michael Jackson stole the spotlight after he dangled his baby Prince Michael II over his balcony in Berlin to fans. He later admitted he regretted the wild move. “I got caught up in the excitement of the moment. I would never intentionally endanger the lives of my children,” Jackson said.


Lots of celebrities were dealing with a side of the law they hoped they never would.

R Kelly was tried for child pornography after the alleged infamous tapes of him assaulting an underage girl surfaced — and he was acquitted. But you know what made the most headlines? When Winona Ryder was caught shoplifting from Saks Fifth Avenue. She was caught on camera stealing thousands of dollars of items, which she could afford to buy. Ryder later admitted in an interview that “‘In a weird way, it was almost like the best thing that could have happened.” Guess some celebrity scandals are a blessing in disguise.


This was weird.

Before Angelina Jolie became Brangelina in 2005, she was making headlines for different reasons in 2000. The star, who had publicly had issues with her father and had gained a bit of a reputation for being a wild child, left everyone confused when she made out with her brother at the Oscars. We’d rather forget about this very weird moment.


One of the worst school shootings led to a strange blame game.

Following the tragic Columbine shooting, which was, at the time, the worst high school shooting in U.S. history, one musician caught a bit of heat for his unintentional influence. Many outlets reported that the shooters had been inspired to commit the crime after listening to Marilyn Manson’s music. It was revealed they were never actually fans of his.

“When it comes to things like Columbine, it would have been different if they [Harris and Klebold] had actually liked my music, but I think that I have had more blame accredited to me then any person in the history of music,” said Manson. “There should be some sort of Grammy for that.”


Politicians have had their messy moments.

The Bill Clinton and Monica Lewinsky saga turned the White House upside down. While they both initially denied the allegations, eventually the truth came out. The then-49-year-old President and then-22-year-old White House intern caused global headlines. Clinton was impeached and became only the second president in U.S. history to be impeached after President Andrew Johnson in 1868.


It was a sad year filled with untimely deaths.

Princess Diana, who was dubbed the People’s Princess, was loved across the world for breaking barriers, her charity work, and even for her fashion sense. But after her shocking split from Prince Charles, everything went downhill. Traveling in a car with her rumored lover, Dodi Al Fayed, Diana was involved in a fatal car crash that broke hearts around the world. The same year, New York hip-hop legend and progenitor Notorious B.I.G. was shot and killed in a drive-by shooting. His murderer was never found, and his death remains a complete mystery.


The dramatic moments continued.

In September 1996, Tupac Shakur was killed in his BMW during a drive-by shooting in Las Vegas. The 25-year-old “California Love” star was a hip-hop legend in the making, and his life and career were cut tragically short. This year was also life-changing for Robert Downey Jr.; before he was Iron Man, he was in a tailspin and charged for drug possession.


This was a case that divided the country.

In 1994, Nicole Brown Simpson and her new partner Ron Goldman were stabbed to death in her home, and just days later that they charged someone with the crime— Simpson’s ex-husband and former NFL star O.J. Simpson. The trial took place in 1995, and Simpson was defended by the late Robert Kardashian. One of Simpson’s other lawyers, Johnnie Cochran, coined the famous catchphrase, “if it doesn’t fit, you must acquit,” referring to a glove found at the scene of the crime. Simpson was ultimately acquitted.


One of the fieriest celebrity scandals in pop culture history!

In 1993, the late Lisa ‘Left Eye’ Lopes from R&B group TLC began dating Atlanta Falcons football star Andre Rison. They quickly moved in together and after some alleged abusive behavior, Left Eye was done. On June 8, 1994, Rison came home with a pair of new sneakers without a pair for Left Eye. After a late evening/early morning fight that went into the next day, she burned down their Atlanta mansion. She fled before later turning herself in to police.


Michael Jackson made headlines for his off-stage behavior.

In 1993, the King of Pop was accused of assaulting a 13-year-old boy. The scandal rocked the world and opened up years of investigation into Jackson’s relationship with young boys. Not only did it force Jackson to cancel his tour, but it caused heated debates among fans, journalist, and critics. Jackson ended up settling the case outside of court for $23,000.


A controversial family affair erupted.

Woody Allen and Mia Farrow split up after 12 years of marriage. Prior to their relationship, Farrow had adopted a daughter, Soon-Yi Previn. But following Allen’s divorce from Farrow, a strange thing happened. Allen began dating Soon-Yi (who is 40 years younger than him). The couple made their relationship public in 1992. This is one of those celebrity scandals that feels eerily relevant, given the #MeToo movement.


This was a rom-com gone wrong.

In 1991, Hollywood sweetheart Julia Roberts and bad boy Keifer Sutherland were quite the It Couple. Roberts, who was known for her slew of rom-com roles, ended up bringing a movie-inspired storyline into real life. After the two were set to get married, Roberts ditched Sutherland just three days before their tremendous wedding. The best part? She left Sutherland for his friend Jason Patric.


We’ve seen our fair share of lip-syncing fails and celebrity scandals over the years, but nothing tops this.

During the ’80s, Milli Vanilli had it all, including a bunch of number one hits and a Grammy Award for Best New Artist. They were lauded for their stylish looks, dance moves, and seriously sharp shoulder pads. But everything fell apart during a performance for MTV. As they were performing their hit, “Girl You Know It’s True,” their live backing track began to skip, exposing that they had been lip-syncing all along. Eventually, it came out that the duo didn’t even know how to sing and were just a creation of a very cunning producer.


Madonna became the queen of controversy.

In 1989, Madonna went number 1 with her controversial hit, “Like A Prayer.” The video, which saw Madonna rush to a church for solace, meet a wax saint in a cage, and fall in love with the now-alive statue made a lot of people angry. At the time, the pop star had a deal with Pepsi and after outrage from right-wing Christian groups, Pepsi canceled their deal with Madonna.



Strangely, this is one of those celebrity scandals has been long-forgotten.

Before Rob Lowe became a television favorite on Parks and Rec, he was a child star. But somewhere between being a young actor and a millennial fave, Lowe had his own sex scandal. In 1988, Lowe videotaped himself having sex with a 16-year-old girl (the age of consent at the time was 14) he met in a nightclub. The tape later leaked. Lowe ended up slammed with a huge civil suit from the girl’s mother.


Matthew Broderick was involved in a fatal crash.

The Ferris Bueller’s Day Off star was just 25 years old when he was driving on a stormy night and lost control of his car, crashing into another vehicle. While Broderick had some minor injuries, he was fine and so was his passenger, his then-girlfriend actress Jennifer Grey. But the passengers in the other vehicle were both killed. Broderick was charged and convicted of careless driving.


Jack Nicholson was Hollywood’s bad boy, but in 1986, some of his past mistakes came back to haunt him.

Jack Nicholson and Anjelica Huston dated on-and-off from 1973 to 1989. Huston later revealed that not only did he laugh off the idea of marrying her, but she also had to put up with his womanizing ways. One woman in particular, Susan Anspach, claimed to have given birth to one of Nicholson’s children just a few years later. Nicholson’s kids started adding up, and he has had a total of five children with four women.


This paparazzi assault involved Madonna.

Sean Penn was another actor in Hollywood who had a reputation for his bad-boy attitude. While he was married to Madonna, Penn got in an altercation with a paparazzo for trying to take a photo of the pair. His assault almost landed him in jail, but he ended up only suffering a $100 fine. His 90-day jail sentence was suspended, and after paying his fine, he was one his way — isn’t that how most celebrity scandals go?


The world mourned the tragic loss of Marvin Gaye.

Better known to some as the Prince of Motown, Marvin Gaye was and still remains one of the most legendary soul singers of all time. On April 1, 1984, the singer got into an argument with his father, Rev. Marvin Gaye Sr. The two had always reportedly had a tense relationship, and this fight was their last; Gaye Sr. shot and killed the 44-year-old crooner.


The Miss America pageant crowned their first Black queen.

And that queen was Vanessa Williams. But Williams’s reign ended abruptly after Penthouse published nude photos she had posed for years before. While she consented to her photos being taken before she was crowned, she did not give the magazine permission to publish the photos after the fact. That didn’t matter to the Miss America committee, though. She was stripped from her title, and only in 2017 did she receive an apology from the pageant.


Some legends — and celebrity scandals — never die.

Before his stint on reality TV, Ozzy Osbourne was one of the hardest rock and roll stars in the world. Known for his onstage antics, Osbourne took things one step too far when he bit the head off a bat during a show in 1982. He was in the middle of a performance when the bat landed on stage— but he maintains he didn’t know the bat was real.


The death of Natalie Wood remains one of Hollywood’s biggest celebrity scandals.

Wood, known for her roles in West Side Story and Miracle on 34th Street, was just 43 years old when she died. Apparently, the star went sailing on her family yacht with her then-husband, Robert Wagner and friend Christopher Walken. But the following morning, Wood was discovered dead, floating in the water. While at first it seemed like an unfortunate case of drowning, a cause of death has never been discovered. Things got especially suspicious after it was discovered Wood has bruises on her body and drugs in her system. The case is still unsolved.


In 1980, CBS banned this series of Calvin Klein ads.

The television and print ad, which featured a suggestive 14-year-old Brooke Shields, caused an uproar. The model and actress posed suggestively while wearing CK’s signature jeans. In the video advertisement Shields teasingly says:  “Do you know what comes between me and my Calvins? Nothing.” Of course, the controversial ad ended up serving the brand well, whose sales shot through the roof.