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19 Most Cringe 2000s Pop Culture Moments That Are Iconic Now

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The 2000s were packed with major pop culture moments that left the entire world in a state of shock. From high-profile lip-syncing disasters to explosive cheating scandals, Hollywood celebrities were constantly under the microscope during these viral turning points. Whether it was a live television blunder or a legal battle that dominated the headlines, these infamous stories completely defined the aesthetic and drama of the decade. Here are the most memorable instances that still make us cringe today:

1.To start, when Ashlee Simpson was accidentally caught lip-syncing during her performance on Saturday Night Live in 2004:

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Dana Edelson / NBCU Photo Bank

2. When Janet Jackson endured a massive wardrobe malfunction after Justin Timberlake exposed her breast during the Super Bowl XXXVIII halftime show in 2004. This controversial incident famously became known as “Nipplegate”:

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Frank Micelotta / Getty Images

3. When Kanye West stormed the stage and interrupted Taylor Swift’s acceptance speech at the 2009 MTV VMAs, where he famously declared that Beyoncé had “one of the best videos of all time”:

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Jeff Kravitz / FilmMagic / Getty Images

4. When Winona Ryder faced serious legal trouble after being charged with shoplifting $5,500 worth of luxury designer goods from Saks Fifth Avenue in 2001:

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Steve Grayson / WireImage / Getty Images

5. When Michael Jackson caused a global media frenzy by dangling his infant son over a hotel balcony railing in Berlin back in 2002:

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Getty Images

6. When Michael Vick was officially indicted, suspended from the NFL, and eventually sentenced to 21 months in federal prison for his leadership in an illegal dog-fighting ring in 2007:

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Bob Leverone / Sporting News via Getty Images via Getty Images

7. When R. Kelly faced a long series of sexual misconduct allegations and was indicted on charges related to child sexual abuse images during the early ’00s:

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George Mcginn / Getty Images

8. When Mel Gibson sparked massive backlash for making anti-Semitic and sexist remarks during his high-profile DUI arrest in 2006:

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Vera Anderson / WireImage / Getty Images

9. When Martha Stewart was convicted for her role in an insider trading scandal following a widely publicized six-week trial in 2004:

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Gregorio Binuya / Getty Images

10. When Brad Pitt, Angelina Jolie, and Jennifer Aniston had to navigate an incredibly messy and public love triangle that obsessed tabloids in 2005:

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Jeff Kravitz / FilmMagic / Getty Images, James Devaney / Getty Images

11. When Lil’ Kim was convicted of perjury in 2005 after she was caught lying to a grand jury regarding a shooting incident involving her entourage:

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Jemal Countess / WireImage / Getty Images

12. When Paris Hilton and Nicole Richie went from being inseparable best friends to bitter frenemies during their explosive 2005 friendship fallout:

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Jamie Mccarthy / WireImage / Getty Images

13. When Jude Law issued a shocking public confession in 2005, admitting to cheating on his fiancée, Sienna Miller, with their children’s nanny:

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MJ Kim / Getty Images

14. When Chris Brown was officially charged for physically assaulting his then-girlfriend Rihanna in 2009, a dark moment that changed his career forever:

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MARK RALSTON / AFP via Getty Images

15. When Kate Gosselin filed for divorce from Jon Gosselin after multiple cheating allegations surfaced in 2009. The reality stars had been married for a decade and shared eight children:

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Brad Barket / WireImage for Discovery Communications / Getty Images

16. When Tara Reid suffered a highly publicized “nip slip” after her dress strap slid off her shoulder while posing for photographers at a party in 2004:

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DMIPhoto / FilmMagic / Getty Images

17. When Tiger Woods’s extensive extramarital affairs were brought to light in 2009, signaling the dramatic downfall of his marriage to Elin Nordegren:

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ROBYN BECK / AFP via Getty Images

18. When the infamous Kim Kardashian and Ray J sex tape was leaked in 2007, a moment that arguably launched the modern era of reality TV fame:

John Shearer / WireImage / Getty Images

19. And finally, when Tom Cruise frantically declared his love for Katie Holmes by jumping up and down on Oprah Winfrey’s yellow couch in 2005:

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ABC

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Barry Keoghan Denies Sabrina Carpenter Cheating Allegations

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Barry Keoghan is finally opening up about the viral cheating allegations involving Sabrina Carpenter following their high-profile breakup.

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Phillip Faraone / Getty Images for ABA

To get you up to speed: After news broke that Barry and Sabrina reportedly split in late 2024 after a year of dating, the internet was flooded with rumors that he had been unfaithful to the “Espresso” singer with influencer Breckie Hill. For her part, Breckie quickly shut down the cheating speculation on her own platforms.

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Dave Benett/VF24 / WireImage for Vanity Fair

Despite the denial, the wave of online negativity aimed at the Saltburn star was so intense that he eventually felt forced to delete his Instagram account and release a statement regarding the “hate” he was enduring during that period.

Victor Boyko / Getty Images

While appearing on a recent episode of the Friends Keep Secrets podcast, Barry addressed those persistent cheating rumors directly. He shared a candid look at how the public narrative has fundamentally altered his life—and his perspective was truly heartbreaking.

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Steve Granitz / FilmMagic

“I came off Instagram and social profiles,” he confessed during the interview. “I’ve stopped going to events. I’ve stopped, you know, just, socializing. It’s because, you know, there was a narrative out there that was never really sort of even spoken on, a narrative that’s not true, and I never confirmed or said anything about it. And, you know, I just disappeared.”

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Robert Okine / Getty Images

Reflecting on the unique struggles of “having a relationship in the public eye,” Barry pointed toward the video where Breckie denied the rumors. “No one seemed to latch on to that video,” he noted, expressing frustration over how the public perception has shifted since the breakup.

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Araya Doheny / Getty Images for SAG-AFTRA Foundation

“I’m not asking for people to become my fan and like me because that’s not normal either,” he continued. “But I’m asking for people to stop assuming and also stop jumping on this narrative and attacking me and dragging me down in any way you can, involving my parents who are no longer with me… just absolutely disgusting and vile. There’s videos on TikTok literally going, ‘I hate him.'”

Theo Wargo / Getty Images

Watch the entire interview here:

Friends Keep Secrets / Via youtube.com

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Billie Eilish Addresses Rumors of a Falling Out With Finneas

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Billie Eilish and her brother Finneas (frequently stylized as FINNEAS) have solidified their status as the most formidable songwriting team in modern pop. Together, they have secured multiple Grammys and Oscars, building an impressive catalog of global hits that continues to expand.

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Jeff Kravitz / FilmMagic

Recently, rumors began circulating that the iconic sibling duo might be experiencing some friction. While the whispers may have bypassed some, they certainly reached Billie. In a candid new interview with Elle, the “Birds of a Feather” singer addressed these falling out rumors directly to clear the air.

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Variety / Variety via Getty Images

“I heard somebody say, ‘Did you guys hear Finneas and Billie had a falling-out?’” Billie recounted during the interview. She followed up with a definitive statement regarding their bond: “Finneas and I have never and will never have a falling-out, ever in our lives.”

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Matt Winkelmeyer / Getty Images for The Recording Academy

“We’ll get in the biggest fucking fight you’ve ever heard of in your life…and five minutes later, we’re back, laughing and making music,” she explained. “It’s sibling shit. There’s nothing else in the world like sibling relationships.” It is a sentiment many with siblings can certainly relate to.

Jeff Kravitz / FilmMagic

While discussing their dynamic, Billie also touched upon the daunting prospect of potentially not collaborating with Finneas one day. Her take on the future of their professional partnership was both refreshingly honest and surprisingly open-ended.

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Jeff Spicer / Jeff Spicer/Getty Images

“If I never saw Finneas at all, I might literally never make a song again,” she mused, before posing a deeper question about their personal growth: “But how do we move on and have separate lives?”

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Michael Blackshire / Los Angeles Times via Getty Images

It is the classic dilemma that defines almost every legendary creative partnership. As fans ponder the future of their favorite musical duo, the full profile offers even more insight into Billie’s current world.

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Shannon Elizabeth OnlyFans Earnings: American Pie Star Wealth

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If you’re a millennial of a certain age, you know Shannon Elizabeth from a few things. Between the American Pie franchise, Tomcats, Scary Movie, and even a Jay and Silent Bob movie or two, she was arguably one of the queens of the “movies you watched at a sleepover party” subcategory.

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©Universal/Courtesy Everett Collection

Shannon’s acting career has remained fairly steady since then, but she recently took on a new role entirely: OnlyFans creator. She joined the service just a few weeks ago, telling People at the time that starting her own OnlyFans was because “I’ve spent my entire career working in Hollywood, where other people controlled the narrative and the outcome of my career. This new chapter is about changing that, showing off a more sexy side no one has seen, and being closer to my fans.”

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Kayla Oaddams / Getty Images

Well, just a few weeks later, People has a new report on how the OnlyFans foray is going for Shannon — and as it turns out, she’s seemingly struck content-creator gold in the process.

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©Columbia Pictures/Courtesy Everett Collection

A source tells the publication that Shannon brought in “more than seven figures” on the first week she joined OnlyFans. Seven figures! Let that sink in.

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Tiffany Rose / Getty Images for GBK Brand Bar

The source adds that Shannon “is really making a name for herself” on her page, and they also note that there is no full nudity featured on it. “She is super happy she now gets to take control and be engaged with her fans,” the source adds.

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Shirlaine Forrest / WireImage

See, this is what Margo was thinking when she said she had money troubles…we’ve reached out to Shannon’s reps for further comment and will let you know if we hear anything back.

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