Top 10 Celebrity Scandals of Each Year (2000-2009)

Angelina Jolie stunned everyone when she took the term 'sibling bond' to a new level after locking lips with her brother on the red carpet in 2000! Jolie's method of celebration after winning the Oscar for Best Supporting Actress was publicly showering her brother, James, with loads of affection in her acceptance speech and sharing a scandalous smooch with him later on. By now, we're used to knowing how Jolie handles public scrutiny. However, in this early 'flirtationship' with the media, we were able to see Jolie's "tell it like it is" attitude on display when she attempted to squash rumors about her and James’' relationship to “People” magazine explaining, "It was disappointing that something so beautiful and pure could be turned into a circus."

Unfortunately for indie darling Winona Ryder, reality began to 'bite' in 2001 after footage of Ryder swiping several items from Saks 5th Avenue surfaced; The grainy video even showed security personnel following her out of the store and questioning the actress. After she was sentenced in 2002, Ryder was captured famously reacting to the judge's treatment of her while in court. Watching the woman who affectionately befriended outcasts in her films and helped define Gen-x culture with her laidback nature be described as a "double felon," would definitely warrant an explanation to Edward Scissorhands. Publicly talking about mental health was definitely not the norm in the early aughts, making Ryder's eventual explanation of desiring the chaos in her life at the time to "stop" extremely poignant in hindsight.

2002: Eminem’s War of Words with the Cheneys

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Top 10 Eminem Feuds

Speaking out against authority can be admirable, but there are likely consequences around the corner. Eminem found this out after his criticism of then-second family, the Cheneys, landed the rapper in hot water. Some context: for some time, Lynne, the wife of Vice-President Dick had been making it her ‘job’ to express her distaste for him, calling Eminem out during Congress hearings in 2000. Two years later, Eminem channeled his frustration over their politics and power by showing Dick being electrocuted in "Without Me"’s music video and cursing Lynne out in “White America”’s lyrics. During a time where patriotism and unity were on the rise in the US following the September 11th attacks, Eminem's decision to ignore the status quo and maintain his outspoken artistry was shocking, even for Slim Shady!

Take two trailblazing figures in entertainment who are well familiar with the magic of stage theatrics, and toss in a jaw-dropping twist, and you have Britney Spears and Madonna's culturally defining performance at the 2003 MTV Video Music Awardss! Paying homage to Madge's legendary wedding-themed performance of “Like A Virgin” at the same ceremony 19 years earlier, Madonna kissed her two 'brides' (yes, Christina Aguilera was also there!); the smooch may have lasted only a few seconds, but the wildly important influence of two notoriously criticized performers exerting their power and shifting the public's attention back to basics, lasted much longer - and reminded us why Britney and Madonna's showmanship remained supreme.

It was the 'flash' seen around the world and an incident that would redefine live performances forever. Superstar Janet Jackson and boy band wonder-turned-solo-sensation Justin Timberlake were the entertainment for the 2004 Super Bowl Halftime show, but one of their choreographed moves truly captured the public's attention: in a strategically planned dance move, Timberlake meant to uncover part of Jackson's costume, but instead revealed her breast during the line ["Gonna have you naked by the end of this song"] in "Rock Your Body." This sudden slip helped shed light on the rigid expectations society holds for female performances versus their male counterparts; while the career-altering repercussions that Janet endured following the wardrobe function certainly weren’t as drastic, Ashlee Simpson also saw her career take a turn that same year after she performed on SNL famously using a backing track.

Watching an idea of perfectionism unfold especially when famous people are involved, brings a sense of humanity to the idea many of us have around the word 'celebrity.' Take one of the biggest scandals of the decade and certainly one of the biggest news stories of the year; America's sweetheart Jennifer Aniston had to publicly process feelings of "shock and confusion" as described by “Vanity Fair” when she split up with her husband of five years amid rumors that Brad Pitt left her for his “Mr. and Mrs. Smith” co-star Angelina Jolie. Suddenly, fans and celebrity gossip gurus alike were seeing Aniston, Pitt, and Jolie as real people going through a universal experience, showing that in reality, celebrities truly can be just like us more than we realize.

The lines between fact and fiction were blurred in 2006 when a best-selling memoir with a now-iconic cover featuring a hand covered in colorful sprinkles was revealed to be largely fictitious. After legendary queen of daytime TV and valuable recommendations, Oprah Winfrey endorsed James Frey's autobiography “A Million Little Pieces'' for her book club, the book suddenly became massively popular. She also found herself having to bring Frey into the hot seat following a bombshell report revealing his storytelling contained "wholly fabricated," and "wildly embellished details," completely redefining the book's legacy. Frey's downfall from his shortcomings and Oprah's persistence in the interview showed a celebrity being held accountable to the world, and how success can be pretty fleeting.

Back in 2007, the media seemingly loved nothing more than to tear down divas who ruled headlines, indulging in the celebration of their downfall. Remember when a certain hotel heiress was ordered back to jail to serve the rest of her original 45-day sentence only one day after she resentenced by the Los Angeles County Sheriff to 40 days of house arrest? Though Paris Hilton ultimately spent only half of her full sentence in a detention facility, spectators of Hilton and her high-profile status were captivated by the superstar's tear-filled sentencing. Another leading lady of the year's headlines from an equally famous family as Hilton's, Jamie Lynn Spears, also got the temperamental tabloid treatment after announcing her pregnancy at sixteen years old (xref). The aughts were definitely a decade known for pesky tabloid finger-pointing at successful women.

2008: Tom Cruise’s Scientology Video

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Top 24 Celeb Scandals of Each Year (2000-2023)

In the 2000s, it was hard to take our eyes off of Tom Cruise. Cruise provided plenty of can't-look-away antics in the mid-Aughts; he kissed and couldn't wait to tell, and he made sure the world knew exactly what his thoughts were on controversial subjects. By 2008, we were used to hearing Cruise's outlandish opinions to the point of nearly shrugging them off, but then came the infamous video featuring the actor expressing his views on the world based on his religion of choice: Scientology. Needless to say, more than a few eyebrows were raised! Cruise's seeming descent into a land of 'glib' sparked deeper discussion and speculation over Scientology's influence on his personal life, later inspiring concern for his wife and daughter, and his own wellbeing.

From metaphorical trainwrecks to literal car crashes, the final year of the decade proved to be extremely explosive in celebrity culture! Much like one of the biggest stories of the year, 2009 brought us plenty of moments we couldn't look away from. Taylor Swift's loyal 'Swiftie' fanbase were used to gasp-worthy moments celebrating her success, but nothing could have prepared pop culture devotees for what happened on September 13th. Swift won an MTV moonman for Best Female Video, but her moment of celebration turned sour after Kanye West interrupted her speech, declaring his fanatical belief in Beyonce having ["The best video of all time!"] While this figurative car crash takes precedent, Tiger Woods' actual marriage-ending and career-plummeting wreck also demonstrated the darker side of fame.