Britney Spears: In the early 90’s, Britney would go from a young girl living in Louisiana to a regular actor on Disney’s The All New Mickey Mouse Club. Beginning a trend that would follow Disney stars for the next few decades, she and her co-star Christina Aguilera were quickly spotted as potential pop stars.
By 2000, Britney had proved her pop abilities with hits like “…Oops I did it Again” and “…Baby One More Time”. One of her most iconic moments and a performance cemented in history was Britney at the 2001 MTV VMA’s, where she would perform “I’m a Slave 4 U” in a sparkly two piece with a live albino python around her neck. Her dedication to creating an immersive persona and experience around her performances was clearly visible at just 19. Soon she was on every magazine, every talk show, and was the subject of a poster in every girls room. She had opportunities like performing at the MTV Super Bowl halftime show, a role in the movie Crossroads, and became the youngest person to act as host and musical guest on SNL.
However, the trajectory of her fame was too much to handle, and things started to go wrong after her very public relationship and torrential breakup with Justin Timberlake. The pair were in a relationship from 1999 until 2002, when Justin quickly pinned the breakup on Britney and used his influence against her in the media. In early 2004, she drunkenly married a childhood friend in a Vegas chapel before getting an annulment, an altogether silly and forgetful joke for most young people, but the media used it as even more ammo against her. She got married again in 2004, to one of her backup dancers named Kevin Federline. Despite a year full of tumultuous relationships, her talent and fame would continue to drive her and she took home her first grammy for “Toxic”.
Just 23 year old, married Britney had two children with Kevin, but was still acting erratically at times and had to care for her children under the constant scrutiny of paparazzi. Because of these stressors and Kevin often being gone for work, they got divorced in 2007. He was given sole custody of their children after telling a judge that Britney had substance abuse problems, and her public image was no help.
2007 and 2008 were the roughest years for Britney publicly, she was vilified by the media- her face, body, lifestyle, and parenting skills or lack thereof were all up for discussion on every tabloid in every town in America. While society still hasn’t fully figured out how to treat celebrities like people, it is hard to realize the level of absolutely inhumane treatment she received. In hopes of achieving some control and losing the media’s interest in her appearance, she shaved her head, but this act ultimately had the opposite effect.
She was placed under a conservatorship and hospitalized multiple times at the end of the decade. However, she continued to put out albums and perform while under this conservatorship. In 2019, people started to question why, 15 years later, adult Britney needed this and fought for her to be released from the last bit of what they saw as media control. #FreeBritney and a popular documentary helped to get her some freedom back and exposed the roles of people such as her family, Justin Timberlake, and paparazzi for their treatment of her.
Paris Hilton vs. Lindsay Lohan: The 2000s were the pinnacle of celebrity saga, and one of the few feuds was as iconic as the battle between Paris Hilton and Lindsay Lohan. Once Hollywood party scene acquaintances, their friendship turned into an all-out war, fought in paparazzi photos, red carpet cocktails, and online quotes.
The feud escalated in 2006 when Lindsay was seen with Paris’s ex-boyfriend, Greek shipping heir Stavros Niarchos. Around the same time, a clip spread of Paris and frenemy Brandon Davis taunting Lindsay, with Davis famously referring to her as “firecrotch” while Paris laughed in the background. Lindsay tried to brush it off, but the animosity was evident. Lindsay was photographed calling Paris the C-word one night outside a nightclub, then climbing into a car with her and Britney Spears a few hours later. The otherworldly instant left everyone stunned—frenemies or filthy party women?
Their beef continued with passive-aggressive barbs. Paris called Lindsay a “pathological liar” on TV, and Lindsay disparaged Paris’s lack of talent. While both stars faltered personally—Lindsay with legal issues and Paris with jail time—their feud eventually burned out.
Now, years later, both of them seem to have moved on. Paris is a mom and entrepreneur, while Lindsay is working as an actress and living her family life. Though drama is in the past for them, the feud itself is one of the most epic pop culture flashpoints of the 2000s.
Lindsay Lohans Legal Troubles: Lindsay Lohan was the golden girl of Hollywood, but by the turn of the 2000s, her movie career was dominated by a succession of legal problems, rehab stays, and courthouse appearances. Once a Mean Girls star, she went from red carpet to mugshots, and became the decade’s most notorious tabloid fixture.
Her issues began in 2007 when she was arrested twice for DUI and possession of cocaine within three months. She entered rehab a number of times but could not stay away from temptation. Having broken probation, she spent 84 minutes behind bars—yes, minutes, because of overcrowding.
They continued to worsen in 2010, when she skipped a court-ordered alcohol education course and was caught partying in Cannes instead of going. A judge sent her to 90 days’ worth of jail time, but once again, she only served 14 due to overcrowding. Her career was in full-on free fall at this point.
Lindsay’s probation violations kept piling up and landing her in the slammer again and again for theft, assault, and even giving false information to the police about a car crash. Between 2007 and 2013, she was behind bars and rehabbing six times, with more mugshots than there were movie credits to her name.
Later, Lindsay escaped Hollywood and moved to Dubai, away from the paparazzi circus that had contributed to her downfall. Though she has attempted a comeback since then, her legal troubles are one of the most iconic (and tragic) cautionary tales of early 2000s fame.
Jennifer Anniston and Brad Pitt: Jennifer Aniston and Brad Pitt were introduced by their respective managers in 1994. At this time, Anniston was relatively unknown and had just begun her run on Friends, while Pitt was on his way to becoming the movie star we know today. They were in separate relationships at the time, and wouldn’t meet romantically until 1998, when the same managers set them up on a blind date.
The couple split from Hollywood norms by keeping their relationship a secret for over a year. Therefore, their first red carpet appearance together at the September 1999 Emmy awards made every magazine. Their projected status as an ‘It’ couple was clear from the beginning. Just over a month later, the couple announced their engagement.
They would choose to keep things private again for the wedding, reportedly spending over 1 million dollars on the day, with part of the budget spent keeping paparazzi out of the venue. They got married July 29, 2000, at a beautiful cliff in Malibu, with celebrities like her friends costars, Salma Hayek, and Cameron Diaz in attendance.
The couple lived in what seemed to be a happy marriage for years, working on their separate movies and attending events together. Pitt made a hilarious guest appearance on Friends and they even made a production company together called Plan-B Entertainment which produced over 15 movies. By 2004, Anniston had told a reporter she felt ready to have children with Pitt.
However, this is also when things seemed to start falling apart for the couple. In 2004, Brad Pitt began filming Mr. & Mrs. Smith with Angelina Jolie and rumors swirled about their on-set chemistry, though both deny any infidelity at the time even today. Their marriage ended officially when Anniston filed for divorce a year later citing irreconcilable differences.
During the early breakup days, Aniston and Pitt would both tell the media that they would “still be friends” and had no hard feelings for the other. However, the triangle involving Angelina Jolie was too enticing for media and paparazzi to leave alone. Both parties were forced to answer questions and see tabloid stories about a relationship they were no longer in.
People finally loosened their grip on the past couple when Pitt and Jolie got engaged, we say ‘finally’ because it took 10 years. Society became so enthralled with the new couple, they became known as “Brangelina”. Ultimately the couple would only be married for two years before going through a much tougher, public divorce that took 8 years, ending in December of 2024.
Taylor Swift V. Kanye West VMAs: 2000’s drama could be found at any year during the decade, so we’ve included one of the latest for fun. At the 2009 VMA’s, both Taylor Swift and Beyoncé were nominated for Best Video by a Female Artist for “You Belong with Me” and “Single Ladies” respectively. When the awards were announced, Taylor was the winner and she was . She walked up to the stage to receive her award and began her acceptance speech, in shock like any 19 year old would be, when Kanye West ran up onto the stage.
He grabbed the microphone from Taylor and said these now infamous words, “Taylor I’m really happy for you, I’m gonna let you finish, but Beyonce had one of the greatest videos of all time
While Taylor today is one of the most successful pop stars ever, she had only put out two albums and was not widely known outside of country music. Many years later she said that because of this, she thought the booing crowd was angry at her for winning, not at his actions.
Later in the night, Beyonce was given performance time due to her other wins and invited Taylor up to finish her speech.
Kanye received widespread and immediate backlash from a wide variety of sources, including other celebrities, fans, and actual U.S. President Barack Obama, who was leaked on a hot mic calling Kanye a “jackass”. However, others thought that despite Kanye’s actions being wrong, Beyonce deserved the award and it wasn’t a big deal. The main thing was, everyone had an opinion they wanted to talk about. Articles like this one from Vox even argue that the VMA’s moment was essential in defining Twitter as a medium for conversations. That’s how big this moment was.
Taylor answered a few questions after the show but wouldn’t say whether or not she still ‘liked’ Kanye, however she said she was a fan before the incident. Kanye has apologized multiple times in interviews and on social media, but has just as often taken the apology back and said he doesn’t regret it, so it’s hard to know.
