The Most Memorable MTV VMA Moment of Each Year (2000-2009)

May we have your attention, please? Will the real Slim Shady please stand up? No, seriously--we can’t find him in the crowd of lookalikes! The 2000s were a simpler time and that’s also true for award shows. What performances lacked in refinement, they made up for in energy and shock value. No one knew what Eminem had in store for his performance, so when he opened on 6th Avenue with a lineup of what seemed like 100 versions of himself--all with bleached hair and white tees--the crowd didn’t know what to make of it! The message is pretty clear: there are tons of people out there like Eminem, but only one that’s the real deal.

If you’re scared of snakes, we’ll give you the warning now. How Britney performed this without missing a single note is beyond us. The song begins with the starlet locked in a cage with a literal tiger. She frees herself, puts on a downright enchanting performance for the next two minutes, and then approaches one of the dancers with a live snake on her shoulders. They transfer the python onto Britney’s shoulder where she parades it around the stage for a while. Her voice doesn’t wobble--not once. We’re not claiming Britney is a snake charmer but… she’s a snake charmer. Did we mention she was only 19 at the time?

The VMAs are always special for artists, but the 2002 VMAs were, in particular, pretty special for Michael Jackson because it also happened to be his 44th birthday. The award show decided to celebrate, and had Britney Spears present a cleft-shaped trophy and a giant birthday cake. In her birthday wishes speech, she referred to him as someone she thought of as “the artist of the millennium”. You can see how this might be misinterpreted by the King of Pop, who walked on stage and accepted what he believed was a new award: the artist of the millennium. Honestly, if he really had won an award under that name, there aren’t a lot of people who would bat an eye. Certainly, a birthday to remember.

There might not be a more iconic VMA performance. As an homage to Madonna’s performance at the first VMAs, the song now featured three of pop’s biggest names. Britney Spears began the opening lyrics to “Like a Virgin” in a wedding dress atop a giant wedding cake. Christina Aguilera walked on soon after in a wedding dress of her own, and it wasn’t long before the Queen of Pop herself made it on, this time in a tuxedo. Just when you thought things couldn’t possibly get more epic, Madonna leaned over and planted a passionate kiss on Britney’s lips before doing the same to Christina. Cue JT’s face again. Yeah, he was not happy.

2004: Tony Hawk's Skateboarding Stunts “21st MTV Video Music Awards” (2004)

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The 2004 VMAs were the first to include video game soundtracks as a category--the likes of which, to no one’s surprise, were won by “Tony Hawk’s Underground”. Later in the night, Ashlee Simpson and the skateboarder himself presented the award for Best New Artist--but not without a little pizzazz. Tony felt like the stage was missing something and, on cue, it lit up yellow and black for a group of skaters who took to the ramps. (Seriously, they set up the ramps and everything!) Of course, the show wouldn’t be complete without the legendary Tony Hawk shredding things up! And the crowd totally went wild, dude!

2005: Kelly Clarkson's Rainstorm “22nd MTV Video Music Awards” (2005)

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Here’s a performance that really makes you miss pre-Covid days. A barefoot Kelly Clarkson makes her way through a sea of fans to centre stage, high-fiving hands the whole way. Towards the end, 3,000 gallons of water pour down on her and the audience, kicking up the drama of a song that should be impossible to add more to. Luckily, this was before the days of recording with your phone, so it was actually feasible! The energy she puts into this song is unmatched and you can tell she’s really connecting with her fans. We’re torn between deeming this performance thunderous or jaw-dropping!

Let us set the scene for you. It’s 2006. Low-rise jeans are still in and “She’s the Man” just came out. You’re watching the VMAs and Jennifer Lopez announces Panic! at the Disco as the winners of the award for Video Of The Year. This was still pretty early on in the band’s career and they somehow beat out Christina Aguilera, Madonna, the Red Hot Chili Peppers and Shakira, so this was a pretty monumental achievement. Unfortunately, it was crashed by a man named Sixx, who jumped on stage, snatched the mic from Brendon Urie and complained that MTV never gave him his own show. The band took it in stride and made a few jokes, recovering easily enough.

Rivalries between celebrities are not uncommon--especially at award shows--but rarely does it escalate to physical violence. At the 2007 VMAs, lingering tension between Pamela Anderson’s ex-husbands, Mötley Crüe’s drummer Tommy Lee and Kid Rock. There are conflicting reports over whether Pamela Anderson was the source for conflict, but we do know that Kid Rock threw the first punch, although there’s a good chance Tommy Lee said something to spur him on. The real victim here has to be Alicia Keys who was just trying to deliver a good performance… How she kept it up while a full-fledged fistfight was going on is beyond us!

It’s definitely not a secret that 2007 was a rough year for Britney. Her performance at the VMAs that year showed as much but, luckily, it didn’t take very long for her to bounce back. By the time the 2008 VMAs rolled around, you wouldn’t even have known. She won her very first VMA after previously being nominated for years without a win. And not only did she earn her first Moonman that night, but she also won all three of her nominations for Best Female Video, Best Pop Video, and Video of the Year. She was also the celebrity who took home the most awards that night! No one does comebacks quite like Britney Spears!

If you thought Panic! at the Disco’s interruption was bad, Taylor Swift’s is definitely worse. This might be the biggest moment in VMA history, never mind just 2009! Taylor was only 19 at the time and still very up-and-coming. She was so excited to win her first Moonman, but the moment was ripped from her when Kanye West got on stage and stole the mic. In yet another one of his outbursts, Kanye declared that he was happy for Taylor but the award should have gone to Beyoncé. T-Swift thought the crowd was booing her and returned the award, visibly overwhelmed. This moment even managed to overshadow Lady Gaga’s “Paparazzi” performance, which featured fake blood and a symbolic hanging. 2009 definitely wins for most memorable VMA!