1Beyoncé's Baby Bump (2011)
Kristian Dowling//Getty ImagesNot only did this absolute supermom belt out "Love On Top" first, but she danced her butt off before unbuttoning her jacket and revealing her sweet secret.
2Lady Gaga's Bloody Performance (2009)
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3Britney and Madonna's Steamy Kiss (2003)
Scott Gries//Getty ImagesI'm pretty sure this moment actually stopped time for a bit. Oh and then the camera just casually panned over to a newly-single Justin Timberlake, who seemed less than thrilled by his ex's actions.
4Lourdes Leon Makes Her Hollywood Debut (2003)
Frank Micelotta//Getty ImagesBet you didn't know about this one! Madonna's 7-year-old daughter opened her 2003 performance. Today, Lourdes is an über-successful model, to the surprise of no one.
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5Kanye Announces He's Running for President (2015)
Kevin Winter/MTV1415//Getty Images"Yes, as you probably could have guessed by this moment, I have decided in 2020 to run for president," he revealed to the crowd. Ummm, I don't think anybody guessed that, Ye.
6Britney's Scaly Guest (2001)
Scott Gries//Getty ImagesI already knew Britney was 10x cooler than everyone else on the planet in 2001, but her ability to keep her composure while holding an actual python proved it.
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7Travis Barker and Kourtney Kardashian Make Things Official (2021)
Jason Kempin//Getty Images#Kravis made their red carpet debut at the VMAs, jumping right into the excessive PDA we all know and love expect from them during their very first public appearance.
8Eminem Punches a Puppet (2003)
Scott Gries//Getty ImagesAnd that, my friends, is how Eminem got banned forever from Sesame Street. JK, but it was the second time the rapper punched a puppet at the VMAs. The surprisingly violent gag (in which he ripped off the puppet's arm???) was a callback to the year prior, when Eminem got into a real feud with Moby and Triumph the Insult Comic Dog.
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9Alyson Stoner and Missy Elliott Reunite (2019)
Getty ImagesNearly two decades after the pigtailed 9-year-old famously danced with Missy Elliott in her "Work It" music video, they reunited for a performance in honor of Missy's 2019 Video Vanguard Award. It. Was. Everything.
10Kelly Clarkson Brings the Rain (2005)
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11Katy Perry and Niall Horan Kiss (2012)
Lester Cohen//Getty ImagesNobody was more shocked—or thrilled—by Katy's kiss than the One Direction heartthrob himself. "It was amazing and very purple — she had purple lipstick on," he later told Cosmopolitan UK. "I don't think there will ever be anything cooler than kissing her — until I marry her, maybe." You hear that, Orlando Bloom??
12Eminem Performs with Lookalikes (2000)
Frank Micelotta Archive//Getty ImagesFew things are stranger than seeing 30 different Eminems all together at once, and then 20 years later realizing they all kinda look like a blonde Pete Davidson?! Once you see it, you can't unsee it.
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13Pete Davidson and Ariana Grande Go Public (2018)
Kevin Mazur//Getty ImagesSee?? Pete is literally one buzzcut away from being 2000-era Eminem. The comic had a VMAs moment of his own in 2018, when he made his red carpet debut with Ariana. It was literally all anybody could talk about.
14Kanye's Rude Interruption (2009)
Christopher Polk//Getty ImagesIn true, unscripted fashion, Kanye ruined 19-year-old Taylor's shining moment on live TV. It's fine though, because it resulted in "Look What You Made Me Do" (and all of Reputation, really) nearly a decade later.
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15Kanye and Taylor Clear the Air...for Now (2015)
Kevin Winter/MTV1415//Getty ImagesThese two break up and make up more than Khloé Kardashian and Tristan Thompson. In 2015, they famously hugged it out on stage after she presented the rapper with his Video Vanguard Award. As we all know, though, their truce didn't last very long.
16Eva Longoria Wears a Swimsuit (2005)
Kevin Kane//Getty ImagesIn one of the worst-aging and most ill-timed jokes of all time, the actress went on stage and said: "I wasn't going to let a little hurricane stop me from wearing my bathing suit." That little hurricane turned out to be Hurricane Katrina. Of course, she didn't know that at the time, but prepare to cringe watching this one back.
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17Cardi B's Baby Fakeout (2019)
Theo Wargo//Getty ImagesTag yourself: I'm the guy adoringly watching and fully believing that Cardi B brought her baby daughter to the VMAs. As we all know, her bundle of joy actually turned out to be an award.
18Lorde's Interpretive Dance (2017)
Christopher Polk/MTV1617//Getty ImagesDoes the show always have to go on? After Lorde became severely sick with the flu, she chose to skip the singing and dance around the stage during her performance instead. Although it's kinda awkward to watch and left most of the audience confused, serious props to her for going through with it.
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19Cyndi Lauper's Powerful Speech (2021)
Theo Wargo//Getty Images"I won a moon person at the very first VMAs in 1984. Things are a little different now," she said before presenting Justin Bieber with an award. "Yeah, girls wanna have fun. But we also want to have funds. Equal pay. Control over our bodies! You know, fundamental rights." Tell 'em, Cyndi!! 👏 👏 👏
20The Carter Family Gets Emotional (2014)
MTV/MTV1415//Getty ImagesCan you believe just a few months before this pic was taken was the infamous Met Gala brawl? Jay and Bey put all divorce rumors to rest following her epic 15-minute VMAs performance, when they let Blue Ivy present her mom with the Video Vanguard Award. Excuse me while I go rewatch this moment and sob in the corner. It's fine, I'm FINE!
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