The 2026 VMAs are right around the corner. While we all love a good celebrity moment, it took me a while to realize that some of the most iconic moments that are etched in pop culture memory have come to us from the VMAs. So, I dug a little deeper—the VMAs have truly given us some shining celeb moments that are completely unhinged, in both good ways and bad.
Here are 30 iconic celeb moments from the VMAs that are basically pop culture gems:
1. In 1997, Fiona Apple took to the stage and called celeb culture 'bullshit'.
Fiona was 19 when she won the award for Best New Artist for “Sleep to Dream.” Instead of delivering a standard speech, she told the audience that “this world is bullshit” and urged young viewers not to model their lives on what celebrities thought was cool. The speech was considered bizarre and rebellious at the time, but clearly, it has aged well.
2. In 1999, Diana Ross casually cupped Lil Kim's exposed breast on stage.
Lil’ Kim arrived at the VMAs wearing one of the most talked-about outfits at the time: a purple jumpsuit with one breast exposed, covered modestly with a matching pastie. While onstage with Mary J. Blige and Diana Ross to present an award, Ross casually reached over, cupped Kim’s exposed breast, and jiggled it. While Lil’ Kim herself took it sportingly, it left us at the receiving end of one of the strangest celeb interactions broadcast on MTV.
3. At the 2000 VMAs, Eminem performed The Real Slim Shady with an entire army of 'Slim Shady' clones.
Eminem began the performance outside Radio City Music Hall, and marched into the venue with dozens of men dressed exactly like him — bleached hair, white T-shirts, jeans, the whole thing. Talk about unforgettable entrances.
4. In 2001, Britney Spears performed at the VMAs with a literal python on her shoulders, giving us the most iconic pop culture moment of all time.
Britney's performance of I'm a Slave 4 U featured elaborate choreography and jungle-themed staging, which also included an enormous albino Burmese python casually draped across her shoulders.
5. In the 2002 VMAs, Michael Jackson accidentally gave an acceptance speech for an imaginary award.
Britney Spears came on stage to celebrate Michael's 44th birthday, and she introduced him by saying that she considered him to be “artist of the millennium.” Michael apparently thought Artist of the Millennium was an actual award he had just won, so he proceeded to give an emotional acceptance speech for it. MTV later confirmed that no such award existed. Well, to be fair, he did get a literal award in his hand. I'd have assumed that too. But nonetheless, awkward.
6. The 2002 VMAs were a sight to behold. Not only did we have Michael Jackson accepting a nonexistent award; Eminem had not one, but two awkward encounters of his own. For one, he was literally booed for intentionally coming at Moby during his acceptance speech.
After winning Best Male Video, Eminem used part of his speech to insult Moby while the audience started booing. Moby had previously criticized Eminem's music and lyrics, calling them misogynistic. He referred to Moby as a "little girl", after which the audience started booing him.
Not just that—this was also the moment that gave us a real-time glimpse of the ongoing feud between Eminem and Christina Aguilera, who was tasked with announcing his name for the award. A bunch of awkward moments (that we ate up).
7. In the 2003 VMAs, Madonna kissed Britney Spears and Christina Aguilera on stage, making this the image of 2000s celebrity and tabloid culture. If you showed a blurry image of this scene to literally anyone, they'll recognize it in a heartbeat.
Madonna opened the performance with Britney Spears and Christina Aguilera, both dressed as brides in an homage to Madonna's legendary 1984 Like a Virgin performance. And then Madonna kissed Britney. She also kissed Christina, although the broadcast famously cut away to Britney's ex, Justin Timberlake's reaction during part of the moment, which is forever etched into my brain:
8. In the 2007 VMAs, Britney Spears gave a performance of Gimme More during an incredibly difficult period in her life, making it one of the most scrutinized moments in pop culture history.
Britney took to the stage after a highly publicized legal battle for the custody of her sons. Britney had also dealt with immense psychological distress during this period, and the media did not make it any easier on her to deal with it. After getting help and taking time away from the press, Britney made it to the 2007 VMAs. But her performance was heavily criticized, with people commenting on her body, her lack of energy, and basically lip-syncing her way through the song.
9. In 2009, Kanye West walked onstage in the middle of Taylor Swift's acceptance speech and gave us one of the most infamous awards-show interruptions EVER.
Taylor had just won Best Female Video for You Belong With Me when Kanye suddenly walked onstage and took the microphone from her. He then announced that Beyoncé had made "one of the best videos of all time." Taylor just stood there. Beyoncé looked horrified. This is an awards-show moment that somehow became a pop-culture storyline that would continue for YEARS.
Later that evening, after Beyoncé won Video of the Year, she invited Taylor back onstage so she could finish her speech. Well, #girlssupportinggirls.
10. There was more happening in the 2009 VMAs. Lady Gaga performed Paparazzi, started bleeding everywhere, and ended the performance hanging above the stage like she had literally died.
11. And in 2010, Lady Gaga arrived at the VMAs dressed in literal meat. The outfit, designed by Franc Fernandez, included a dress constructed from raw beef, matching shoes and a meat-covered purse. Gaga wore it while accepting Video of the Year award.
12. In 2011, Lady Gaga arrived as her male alter ego Jo Calderone...and simply refused to stop being him.
13. And then Jo Calderone tried to kiss Britney Spears while presenting her with the Video Vanguard Award.
14. It was also at the 2011 VMAs that Beyoncé casually finished performing Love on Top, opened her jacket, rubbed her stomach, and revealed that she was pregnant. The announcement reportedly generated 8,868 tweets per second, which was a Twitter record at the time.
15. In the 2013 VMAs, Miley Cyrus got on stage and made us all feel...things. Uncomfortable things.
First, she came out of a teddy bear and performed her single, We Can't Stop. And then, Miley, and her foam finger, and her tongue went on to accompany Robin Thicke during his performance of the infamous Blurred Lines, and kinda broke the internet.
16. In 2015, Nicki Minaj went on stage, accepted an award, and suddenly hit Miley Cyrus with: "Miley, what's good?"
There had been tension between Nicki and Miley following comments Miley made about Nicki in an interview. So after accepting the award for Best Hip-Hop Video, Nicki finished her speech, looked directly toward Miley, the host of the evening, and publicly called her out.
17. That's not it for the 2015 VMAs. Kanye West accepted the Video Vanguard Award and announced that he was going to RUN FOR PRESIDENT. It's like a time capsule for where it all went wrong.
After an incredibly long standing ovation and a longer acceptance speech, Kanye dropped the bomb. We all know how that ends.
18. In 2016, Drake presented Rihanna with the Video Vanguard Award, confessed he'd been in love with her for YEARS, and then appeared to get his kiss dodged.
Drake gave an extremely personal introduction, telling the audience that Rihanna was someone he'd been in love with since he was 22. And then came the embrace. Drake appeared to move in for a kiss, while Rihanna turned her head and the whole thing became ridiculously awkward.
19. In 2017, Fifth Harmony opened their performance by subtly shading ex-member Camilla Cabello.
By this point, Camila Cabello had left Fifth Harmony. So when the remaining four members appeared at the VMAs, they began their performance standing beside a mysterious fifth figure. When the music started, the fifth person was abruptly yanked backward off the stage.
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