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VOICE OVER: Phoebe de Jeu WRITTEN BY: Don Ekama
These scandals rocked the pop culture world. For this list, we'll be looking at the most shocking controversies involving high-profile figures from each year of the 21st century so far, from 2000 to 2022. Our countdown includes Angelina Jolie's Oscars After Party Kiss, Michael Jackson's Trial, Tom Cruise's Scientology Video, Harvey Weinstein & #MeToo, Meghan Markle & Prince Harry Split From the Royals, and more!

2000: Angelina Jolie’s Oscars After Party Kiss

At the turn of the millennium, Angelina Jolie won the Best Supporting Actress Oscar for her performance in “Girl, Interrupted”. After expressing her undying affection for her brother, James Haven, during her acceptance speech, Jolie locked lips with him at the Vanity Fair afterparty. The widely photographed moment made headlines and sparked rumors about the siblings’ close relationship. What may have been viewed as a questionable publicity stunt by some was later explained by Jolie as being a sincere expression of sibling love. According to a family friend, it was an especially hard day for the two, as they had just been at the hospital with their mom, who was getting treated for cancer.

2001: Winona Ryder’s Shoplifting Incident

“She came, she stole, she left. End of story.” Those were the words used to describe the shocking controversy surrounding Winona Ryder back in 2001. Everyone was stunned when reports emerged that the Oscar-nominated actress tried stealing from a Saks Fifth Avenue store before quickly being apprehended by security personnel. A publicized trial notably resulted in her being fined, in addition to getting community service and probation. The incident was puzzling, as many wondered why anyone would try to avoid paying for items they probably could afford. Ryder eventually explained that her mental health was suffering at the time, a struggle that was only exacerbated by painkillers she was taking.

2002: Michael Jackson Holds Prince Over a Balcony

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The early 2000s were a troubling period for Jackson, in part due to this risky 2002 incident. While staying at a hotel in Berlin, he greeted his fans outside with his young boy Prince Michael II – also known as Blanket. However, the way he presented the child to the crowd, by covering his head with a towel and dangling him precariously over a balcony, left many in absolute horror. After receiving a lot of backlash, Jackson put out a statement in which he apologized for what he termed “a terrible mistake”.

2003: The Chicks Criticize George W. Bush

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Before the events of 2003, when they were known by a different name, the Chicks were country superstars, selling millions of records that proved to be mainstream crossovers. However, that changed when lead singer Natalie Maines openly called out then-President George W. Bush and the looming invasion of Iraq during a UK performance. Her comments didn’t fly in the industry or among country fans, leading to the group members being villainized. The Chicks’ career took a hit and they went on break, but came back with their “Taking the Long Way” album in 2006. Its lead single “Not Ready to Make Nice”, in which they tackle the drama, earned them multiple Grammys, including Record and Song of the Year.

2004: Justin Timberlake & Janet Jackson’s Super Bowl Halftime Show Performance

Super Bowl XXXVIII was a very close and exciting game, only decided by a last minute field goal that cemented the New England Patriots as the winners. But hardly anyone remembers the actual match due to its halftime show. As one of the headliners, Janet Jackson performed her heart out before being joined onstage by Justin Timberlake. While busting moves to his song “Rock Your Body”, Timberlake ended up uncovering Jackson’s breast. The live incident caused an immediate uproar that hurt Jackson’s career for years. It also helped shed light on the vast difference between the societal expectations for male and female artists.

2005: Michael Jackson’s Trial

Jackson was publicly accused of assaulting young individuals on two separate instances. The first case, back in 1993, was closed after Jackson reached a settlement with the victim’s family. In 2005, Jackson would become the subject of a huge scandal. This time, as a result of a second wave of accusations leveled by a cancer patient who had visited his Neverland ranch. The late entertainer was taken into custody and faced multiple charges. After a highly publicized 14-week trial, a jury deemed him not guilty, though further accusations have been leveled against him in the years since. This was also the year of Kanye West’s shot at George W. Bush, though that wasn’t as headline-generating as the Jackson case.

2006: Mel Gibson's Racist Tirade

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2004 saw the release of Mel Gibson’s “The Passion of the Christ”, which came under fire for its portrayal of Jewish people in relation to the crucifixion of Jesus Christ. Two years later, Gibson was driving under the influence when he was stopped by the authorities. After being placed under arrest, he reportedly launched into an anti-Semitic rant. He also allegedly made sexist remarks. TMZ soon reported on the incident, making the details of the confrontation public. Gibson subsequently put out a statement apologizing for the incident, and also expressed his regret with a TV appearance.

2007: Britney Spears’ Struggles

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2007 was the year O. J. Simpson was arrested after carrying out a robbery, years after being acquitted of murder. But when it comes to celebrity scandals, none was quite as unforgettable as the public breakdown of Britney Spears. The pop star had been in the public eye since her teens, when she released her hit debut single “...Baby One More Time”. The pressure of fame and lack of agency at such an early age mixed with her family issues likely created a dangerous combination that damaged her health. This led to her shaving her head, her ex being given custody of their children, and Spears ultimately being placed under a highly controversial conservatorship in 2008.

2008: Tom Cruise’s Scientology Video

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Throughout the 2000s, the life of Scientologist actor Tom Cruise was full of headline-grabbing and often scandalous incidents. From jumping on Oprah Winfrey’s couch to being parodied on “South Park”, he was a regular in the tabloids of that era. Perhaps his most controversial moment came in 2008 when a video leaked online in which he was shown praising Scientology. In the clip, Cruise appears in a black turtleneck and makes a number of questionable claims, all set to the “Mission: Impossible” theme music. The video raised several questions about his state of mind and the influence of the Church of Scientology on his personal life.

2009: Tiger Woods’ Affairs

We’ll never forget Kanye West interrupting Taylor Swift at the VMAs. But 2009 was also the year that Tiger Woods’ seemingly pristine reputation suffered a devastating blow. In November, the National Enquirer reported that he had been unfaithful to his then-wife. A few days later, he was involved in a car crash that further fueled rumors about the state of his marriage. As time went on, numerous women came forward alleging illicit flings with the famed golfer. Woods publicly admitted his guilt on multiple occasions and his marriage to Elin Nordegren ended the next year. He also lost several endorsement deals as a result.

2010: Jesse James’ Infidelity

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The 2009 film “The Blind Side” stars Sandra Bullock as Leigh Anne Tuohy, who takes in and ultimately adopts Michael Oher. Bullock’s performance in the film received universal acclaim and won her the Oscar for Best Actress the next year. And she seemed to shout her then-husband Jesse James out in a quick moment during her acceptance speech. But just over a week after that, news broke that he had cheated on her with numerous women. Soon after James publicly expressed regret, Bullock divorced the “Monster Garage” host, dissolving their marriage in June of that year.

2011: Arnold Schwarzenegger’s Love Child

Extramarital affairs in Hollywood are a dime a dozen. But what made this one pretty shocking was how tight-knit all the parties involved were. Hollywood action star and former California Governor Arnold Schwarzenegger was embroiled in controversy in 2011 when it was revealed that he was the father of his housekeeper Mildred Baena’s son, named Joseph. He reportedly only found out about the paternity some years after the boy’s 1997 birth. Meanwhile, Baena remained part of his family’s staff for nearly 15 more years. After his then-wife Maria Shriver figured things out and went to him, he admitted guilt and apologized to her and their children. Nevertheless, the duo split up.

2012: Jimmy Savile’s Posthumous Scandal

It was the year the U.S. dealt with the shocking Lance Armstrong doping scandal. But across the pond, a more sinister controversy was brewing involving the late Jimmy Savile, a celebrated British DJ and TV host who died in 2011. In 2012, a documentary aired on ITV in which multiple women alleged that Savile had assaulted them when they were younger. This led to a wave of accusations and a police investigation, with some incidents said to have occurred on the BBC’s grounds, and others in NHS hospitals. In total, a minimum of about 450 people are believed to have been victims of Savile. In the wake of these revelations, certain distinctions bestowed upon him while alive were withdrawn.

2013: Miley Cyrus’ Image Change

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Miley Cyrus first achieved international recognition for her starring role in Disney Channel’s “Hannah Montana”. The show cemented her as a teen idol, an image Cyrus began moving away from with the release of her 2010 album “Can’t Be Tamed”. After a brief hiatus from music, an edgier, more provocative Cyrus emerged in 2013 with “We Can’t Stop”. As if its lyrics and controversial music video weren’t enough, she gave a raunchy performance of the song and Robin Thicke’s “Blurred Lines” at the VMAs that had many in an uproar. This shift in her public persona was further confirmed by her number-one song “Wrecking Ball.” Its video featured a nude Cyrus on the eponymous equipment and suggestively licking a sledgehammer.

2014: Bill Cosby Assault Scandal

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In August 2014, the celebrity nude photo leak rattled the industry. Roughly two months later, the once-beloved Bill Cosby met his downfall, thanks in large part to a stand-up routine. While performing in Philadelphia in October, Hannibal Buress made a comment referencing long-standing sexual assault allegations against Cosby. After the set went viral and renewed attention on the past accusations, more women came forward alleging that the actor had assaulted them. He went to jail after being convicted of three counts of aggravated indecent assault in 2018. This decision was overturned three years later after the Pennsylvania Supreme Court found that the prosecution had “violated” his rights.

2015: Rachel Dolezal Race Controversy

It was the scandal that ignited public discussions about race and identity. In 2015, it was reported that Rachel Dolezal, the then-president of the Spokane, Washington chapter of the NAACP, was actually a white woman presenting herself as Black. The news first broke that June following multiple assertions by Dolezal that she had been the target of racially motivated crimes. In response, her mom and dad notably refuted her story, presenting evidence that she was Caucasian. Facing mounting pressure, Dolezal tendered her resignation to the NAACP a few days later. However, she’s said that she “identifies as Black.”

2016: Donald Trump's “Access Hollywood” Tape

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Just one month before the hotly contested 2016 U.S. presidential election, then-candidate Donald Trump’s past problematic remarks were exposed. Back in 2005, he had been caught on tape discussing with “Access Hollywood” host Billy Bush. During their conversation, Trump bragged about harassing women and getting away with it due to his supposed star power. The clip was met with immediate backlash. Trump tried to minimize his comments by referring to them as “locker room banter,” before then putting out a video apology. Still, he tried to place the focus onto his Democratic opponent Hillary Clinton, as well as onto Bill Clinton. The scandal didn’t make as big an impact as many hoped, as Trump was later elected to the highest office in the land.

2017: Harvey Weinstein & #MeToo

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The biggest celebrity scandal of 2017 involved Hollywood producer Harvey Weinstein. In October, Weinstein was accused of harassment, sexual assault, or both by numerous women who worked in the entertainment industry. The allegations, which were revealed by The New York Times and The New Yorker, received widespread attention and ignited an online movement. Under the hashtag #MeToo, many more people came forward detailing their experiences at the hands of other high-profile individuals. This led to several figures such as actor Kevin Spacey and former NBC anchor Matt Lauer being exposed. In 2020, Weinstein was found guilty and handed a 23-year prison sentence.

2018: Allison Mack & NXIVM

Allison Mack, an actress known for her role as high school journalist Chloe Sullivan on “Smallville”, was at the center of a troubling controversy in 2018. She was indicted in April for her involvement in NXIVM, a network marketing company which doubled as a trafficking cult. According to the FBI, Mack — who had joined NXIVM about 12 years prior — found and enlisted women for cult leader Keith Raniere. The recruits were severely mistreated. In 2019, Mack entered a guilty plea. The criminal charges normally would’ve gotten her between 14 to 17.5 years in prison. However, due to the fact that she was repentant and helped the prosecution with their case against Raniere, she was ultimately handed a three-year sentence.

2019: The R. Kelly Revelations

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2019 was the year that Prince Andrew stepped away from his royal duties due to his ties with Jeffrey Epstein. It was also the year in which the long-standing assault allegations against R&B singer R. Kelly caught up with him. Kelly was first charged in 2002 for possession of obscene materials involving youth, although he was eventually acquitted. In 2019, a six-part docuseries titled “Surviving R. Kelly” aired on Lifetime that presented damning evidence against the singer and featured a number of his accusers. Subsequently, RCA Records dropped Kelly, and he was indicted by federal agents on multiple charges. He was later convicted and received a 30 year jail sentence.

2020: Meghan Markle & Prince Harry Split From the Royals

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After getting married to Prince Harry in 2018, American actress Meghan Markle stepped away from Hollywood to become the Duchess of Sussex. What followed soon after was a barrage of criticism and privacy invasion by British tabloids and paparazzi. In January 2020, Markle and Prince Harry revealed that they’d be officially stepping down from their senior royal positions and assuming responsibility for their own finances. The news was met with polarizing reactions. While some supported the pair, especially considering the ultimate fate of Harry’s mother Princess Diana, others, like Piers Morgan, were particularly outraged. The next year, the couple sat for a widely anticipated TV interview with Oprah Winfrey, in which they discussed their experience within the British monarchy.

2021: Britney Spears’ Conservatorship Battle

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In 2008, Britney Spears was placed under a conservatorship that was overseen by her father Jamie and some others. The arrangement, which was reportedly made against her will and was initially meant to be temporary, was later declared permanent, even though Spears’ state of mind had begun to improve. This meant she was no longer in charge of her own personal and financial affairs. As information about the conservatorship made it into the public space, her fans started the #FreeBritney movement. It was amplified and generated headlines with the release of the 2021 documentary “Framing Britney Spears”. In November of 2021, a court ordered the end of the conservatorship after Spears spoke about its damaging effects on her well-being.

2022: Kanye West’s Controversies

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2022 was quite eventful. There was Will Smith slapping Chris Rock at the Oscars. We also witnessed the sensationalized trial between Johnny Depp and Amber Heard. And of course, there were the never-ending controversies of Ezra Miller. In other words, there was no shortage of scandals. But perhaps the most damaging one was that involving rapper Kanye West. He drew criticism in October for wearing a “White Lives Matter” T-shirt. A few days later, after xenophobic comments caused his Instagram access to be revoked, West tweeted more anti-Semitic remarks. His behavior on these platforms and elsewhere led to multiple brands and companies dropping him, which in turn meant he was no longer a billionaire. West has since continued with his rhetoric.

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