The 25 Most Memorable Performances at the MTV Video Music Awards

It’s hard to call the early 2000s the “peak” of Bad Boy’s success because they dominated during the 1990s and transitioned into the Dirty Money era as we hit the 2010s, but 2000 to 2002 was definitely a key moment. Diddy opened up the performance with his 2002 hit “Bad Boys For Life,” eventually bringing out Usher who busted out some of his classic moves for their 2001 single “I Need A Girl.” Ginuwine, Busta, and Pharrell then came out, bringing down the house as usual and turning the VMAs into a party.

TLC is a one of the greatest groups of all time, and they showed that at the 1995 VMAs. Two singers, both of whom were very different from another in terms of singing style, and a dynamic rapper, that blended together beautifully. Showcasing hits from their 1994 album Crazy Sexy Cool, TLC put on a show from start to finish.

Sure we could do the reunion from 2013 which was great, but why that when NSYNC actually had VMA performances from their historic time together? The first performance on a major award show is always memorable, and the group performed their hit songs “This I Promise You,” “Bye, Bye, Bye,” and “It’s Gonna Be Me.” Blast from the past right?

The late, great, Whitney Houston made her mark on the VMAs in 1986 with a medley of her classics “How Will I Know” and “Greatest Love of All.” There weren’t very many artists that could captivate an audience like MTV with a slow ballad, but Whitney being the GOAT she was had the crowd glued to her every moment. Unless we’re wrong, the 1986 VMAs were the only time Whitney graced the stage to perform. She would continue to make appearances through the years, but only to present and hang out in the audience.

September is the month of Green Day, so you know we had to include their “Boulevard of Broken Dreams” performance from 2005. If you are anything like us, you definitely had your “air guitar” out for this song and pretty much all the others on American Idiot, so we may have to bring it back one for time for this throwback.

This performance is special because it is TLC’s last VMA performance to date, and of course, the last with Left Eye. In case you forgot, TLC had a serious case for owning the entire year of 1999 with their massive hits “No Scrubs” and “Unpretty,” and the group took to the stage to perform the former. T-Boz and Chilli would return to the VMAs three years later for a special tribute to Left Eye four months after her passing.

Did you put away your air guitar? If so, go on ahead and bring it back out because there isn’t a single soul that didn’t like this song (and if you didn't then we need to have a word.) Hopefully one day when things are a bit safer than they are now, we can go back to having large crowds on stage for extra hype.

So Missy Elliot’s 2019 Vanguard performance doesn’t qualify as a “throwback,” yet but her 2001 VMA performance definitely does. Missy brought out Ludacris, Nelly Furtado, and Trina for a special remix of “Get Your Freak On" and "One Minute Man," while paying tribute to her fallen friend Aaliyah at the end.

Move *car noise* get out the way. One of the most energetic/hype songs of all time deserved a performance spot at the VMAs, and Luda brought the intensity with his 2002 hit Move (Get Out The Way). The entire performance took place outside of Radio City Music Hall in front of a huge crowd. Wish we could have been there.

Get ready because Beyoncé is about to have quite a few entries on this list. The 2003 VMAs was the first time Beyoncé had ever performed at the show (Destiny’s Child included), and all eyes were on Queen Bey for her first performance. Beyoncé started the routine hanging upside down from the top of Radio City Music Hall, and performed smash hits “Baby Boy” and “Crazy In Love” from her debut album Dangerously In Love bringing out Jay-Z for the latter. What a start.

Prince Rogers Nelson had MTV in an uproar with this one, but it’s completely their fault because expecting Prince to “behave” (especially during that time period) was a bit of a generous ask. There is a specific moment in this performance that had corporate VMA up in arms. You’ll have to watch to find out.

2004 was the year of Usher Raymond. These are the undisputed facts. Nothing was stopping Confessions' success on the charts, and Usher had spent the majority of the year making his award show rounds. Naturally the VMAs were on that list, and Usher (or Urrsher as Ludacris calls him) delivered yet another excellent performance. Major throwback for sure.

This is another rare gem from Ms. Jackson. Of course when it comes to Janet’s VMA appearances, many people automatically think of her 1993 performance (which we’ll get into a little later), or even her 2009 tribute to her brother Michael Jackson. This one, however, is up there with being some of Janet’s best ever. 

Beyoncé numero dos. You had to be there. The B’Day era was not to be played with, and Bey was on a mission with her sophomore effort to show that she was gonna be here for a long time. Can we just take a minute to appreciate that dance break though? Sheesh.

Mariah. Carey. If you want to watch a vocal masterpiece, then ladies and gentlemen...her (if you know you know).

This is where the anxiety kicks in because now we are slowly getting down to our last few entries. Early 2000s JLO was a true experience. Jenny From The Block was the first entertainer to have a number one album and movie at the same time, and simply put—JLO was everywhere. You couldn’t escape the “I’m Real” remix. Couldn’t turn on the radio without hearing it, and you definitely couldn’t turn on MTV without seeing the video. JLO and Ja Rule joined forces to perform their smash hit in 2001.

Em’s going to always bring the creativity. How many different “Slim Shady’s” did Eminem have in this performance? It had to have been hundreds. Whatever the amount, Em started off outside Radio City Music Hall with his Slim Shady Look-a-likes for his 2000 hit “The Real Slim Shady,” then brought it indoors to perform his song “The Way I Am.”

Classic Jay and Ye. Few things will ever top the magic of Watch The Throne, and boy does this bring back all the memories. It would have been nice if they could have added in “No Church In The Wild” too, but we digress.

Who could ever forget this? Re-watch this performance and tell us it doesn’t give you goosebumps. Alicia stunned on the piano, brought out the choir, and had the crowd on their feet by the end of the performance. Nothing but pure talent.

This performance is iconic for many reasons: the hysteria of the Janet era, the fact that she performed in jeans and a crop top, and her willingness to bend the rules right until they were about to snap. Of note —Janet’s live renditions of her songs are just as good if not better than the studio versions, and the choreography was sick.

This list wasn’t a ranking so there is no order. However, many still consider Michael Jackson’s 1995 VMA performance as one of, if not the most memorable in MTV history due to his role in really building music videos as a storytelling art form, and the fact that he had never performed on the show before (not even during the Thriller era). Michael made up for all those years of not showing up by performing a medley of his greatest hits leading up to that point.

The network executives at MTV literally had to be sweating bullets during the 1990s. These artists pushed them to the edge with everything they had, but that’s part of what made the 90’s era so great. When you think of that specific time period in the world of MTV, Nirvana almost immediately comes to mind, and they delivered a classic at the 92 VMAs. Long live Kurt Cobain.

Speaking of people who probably made MTV’s heart race a little bit, Madonna had MTV scrambling for their life with her performance of “Like A Virgin.” The song itself was bit risque for the 1980s in terms of its outwardly bold nature, and Madonna took to the VMA stage where she rolled around in a wedding dress, and pushed the boundaries as far as she possibly could.

Since we’re on the topic of Madonna, the Material Girl gave us one of the most iconic moments/performances in MTV history nearly 20 years after that 1984 showing where she took the stage with Britney Spears, Christina Aguilera, and Missy Elliot. In addition to the historic kiss she gave both Britney and Christina, it was the first time that Britney and Christina had ever appeared on stage together for a performance.

Britney shut it down, set it off, and all of the above. This was a performance. And the snake. The snake guys. The VMAs had never seen anything quite like that before, and we’re not sure if we will ever see anything like that again.

Diddy (then known as Puff Daddy) performed a poignant tribute to his friend the late Biggie Small along with Sting, Fatih Evans and 112. Of course as you all know, Sting started his career as the lead singer of The Police, and their single “Every Breath You Take” (which was one of their biggest hits) was sampled by Diddy for “I’ll Be Missing You.”

Diddy started the performance bringing out Sting, with Faith Evans and 112 coming out mid-way through to combine both versions of the song. There wasn’t a single dry eye in the audience that night, and this remains one of the most powerful VMA performances that we’ve seen.

2011 is teetering on the edge when it comes to the “throwback” category, but we had to include this one (especially since we did Jay and Ye earlier). The legend that is Blue Ivy Carter made her unofficial television debut when mom Beyoncé revealed to the world at the end of the performance that she was pregnant. Beyoncé had already walked the red carpet showing off her bump, but since a lot of people don’t watch the red carpet show in its entirety (and social media wasn’t as prominent then), it was still a complete surprise to many. The second best part of this performance by far was Kanye hyping Jay-Z as Bey walked off the stage.