It’s no secret that the MTV Video Music Awards — which first took place in 1984 — has gifted us some of the most iconic moments in pop culture history. Ahead of the 2025 ceremony on September 7, let’s take a stroll down memory lane and remind ourselves of some of the most painfully awkward moments in VMAs history:
1. Nicki Minaj called out Miley Cyrus — who was hosting the show — live on air in 2015 after Miley said that Nicki was “not too kind” for being upset that her song “Anaconda” hadn’t been nominated for Video of the Year. “Now, back to… this bitch that had a lot to say about me the other day in the press. Miley, what’s good?” she said.
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2. That same year, Miley experienced a pretty awkward wardrobe malfunction. During a backstage segment, Miley was filmed hiding behind a curtain that she held over her body — and when her grip loosened, her bare boob was exposed.
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3. Oddly enough, Nicki also experienced a fashion mishap the year prior. While performing “Bang Bang” with Jessie J and Ariana Grande, Nicki expertly held her dress together after it seemingly ripped down the middle.
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4. In 2013, Miley twerked on Robin Thicke during her infamous performance, leaving everyone shocked — especially the Smiths.
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5. When Britney Spears and Madonna famously kissed on stage during their performance with Christina Aguilera in 2003, the cameras panned over to an unimpressed-looking Justin Timberlake (who, of course, broke up with Britney the year prior).
6. Speaking of Britney, she memorably referred to Michael Jackson as “the artist of the millennium” before presenting him with a birthday cake at the 2002 VMAs, which took place on his birthday. However, Michael awkwardly misunderstood and thought that he was receiving an actual “Artist of the Millennium Award” — which, of course, did not exist.
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7. Last year, Chappell Roan was filmed seemingly yelling at a photographer to “Shut the fuck up” on the red carpet.
8. So many celebrities have been accused of lip-syncing during their VMAs performances, including Miley in 2020…
9. …Doja Cat in 2021…
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10. …Anitta in 2022…
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11. …And Shakira in 2023.
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12. Back in 2009, Sasha Baron Cohen, while in his character Bruno, was flying through the venue with his butt cheeks exposed before landing on a very unimpressed Eminem, who left immediately afterwards.
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13. The same year, Lil Mama stormed on stage and crashed Jay-Z’s performance with Alicia Keys — much to Beyoncé’s shock.
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14. In 2005, Fat Joe called out 50 Cent while presenting Missy Elliott with an award.
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15. Nicki Minaj butchered Dixie D’Amelio’s name while introducing her on stage at the 2022 show.
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16. Reporter Jamila Mustafa had a very awkward comment when asked if she liked Lil Nas X’s look in 2021.
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17. That same year, Conor McGregor and Machine Gun Kelly got into an altercation on the red carpet.
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18. Speaking of MGK, he and Megan Fox did NOT shy away when it came to PDA at the 2021 ceremony. Need I mention the awkward tongue touching?
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19. In 2017, Fifth Harmony memorably shaded ex-band member Camila Cabello during their performance of “Angel.”
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20. In 2016, Drake professed his love for Rihanna while presenting her with the Video Vanguard Award — and years later, Rihanna admitted that she found the moment “uncomfortable.”
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21. Let’s throw it all the way back to the 1995 show, when a very drunk Courtney Love threw her makeup compact at Madonna mid-interview. “Courtney Love is in dire need of attention right now,” Madonna awkwardly said.
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22. After seemingly mouthing “shut the fuck up” while One Direction were speaking on stage, Taylor Swift made a dig at her ex Harry Styles while accepting the Best Female Video award for her song “I Knew You Were Trouble” in 2013. She said, “This is just awesome. I also want to thank the person who inspired this song, who knows exactly who he is, because now I got one of these, thank you so much!”
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23. Billie Eilish was accused of shading Jennifer Lopez in 2021 after she was filmed pulling a very unimpressed face at J.Lo’s arrival.
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24. In a somewhat similar vein, Selena Gomez was filmed scrunching her face at Chris Brown’s nomination in the Best R&B category at the 2023 show.
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25. Finally, and arguably the most awkward VMA moment of all time, Kanye West stormed on stage and interrupted Taylor Swift while she was in the middle of accepting the award for Best Female Video in 2009. He said, “Yo, Taylor, I’m really happy for you and Imma let you finish, but Beyoncé had one of the best videos of all time” — while the cameras aptly panned over to Beyoncé, who looked as shocked as the rest of us.
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Which of these moments do you find most awkward? Or, is there another that comes to mind? Let us know in the comments.
You can watch the 2025 VMAs on September 7, at 8 p.m. ET/5 p.m. PT on CBS, MTV, or via Paramount+ in the US.
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