I don’t know about you, but I have spent years upon years watching the VMAs on the edge of my seat waiting for THE pop culture watercooler moments that have taken residence in my brain in a way that I know many could care less about. Maybe it’s also because my brain has been complete and utter mush from the last week of the LA Heat Wave and my inability to confront the fact that the Presidential Debate took place last night (and I can finally exhale after Taylor perfectly timed her Kamala endorsement post-debate. Somebody went to the Tashi Duncan school of rebuttals!! Game, set, match!) - I’ve been using all of my remaining precious energy disassociating thinking about the VMAs taking place tonight.1
In the year of the pop girly, Kendrick Lamar beef, and it is the 40th anniversary of the VMAs - it finally feels like it’s appointment viewing television again after the last couple of weird pandemic-era shows (although, I would argue Lady Gaga’s Chromatica performance is always worth a rewatch).
I think I’ve personally always found myself fixated on the VMAs in part, due to the fact, that I wasn’t allowed to watch MTV growing up. My parents would have no issues with me watching VH1, but had a million problems with MTV - But I’d argue that VH1 was often arguably worse! I remember watching the “I’ll Be Missing You” performance as a tribute to Notorious B.I.G. when I was visiting my cousins and I remember being transfixed. The VMAs scratch the itch of vintage monoculture - whether it was the outrageous outfit Xtina wore in her Dirrty era, Triumph the Dog making an appearance, or one of the many many many iconic Britney performances - there was no greater high than coming into class prepared to discuss it with your friends the next day.
And that’s why it’s time for us all to take a walk down memory lane and discuss my personal favorite (and maybe one of my least favorite) VMA moments of all time to prep us all for the show later this evening:
The Lil’ Kim and Diana Ross Boob Moment (1999)
This is how I know the Mandela Effect is real because I did not remember Mary J. Blige being a part of this moment WHATsoever! And that’s probably because when I saw Diana Ross touch Lil’ Kim’s boob in her Lavender Ferngully-esque fit - it changed the trajectory of history as we know it. Diana walks up to the podium and touches her boob like she’s checking an avocado to see if it’s ripe enough - like it was a normal occurrence for her.
But now that I’ve rewatched this clip with the memory that we had an important third party involved - you see the entire demeanor of Mary J. Blige completely shift and go to another dimension after Diana touches Lil’ Kim and then shifts back into the present after they announce that the Beastie Boys were the winners. This makes complete sense considering what had just taken place and on WWHL in 2020, Mary said that she was angry and that Kim deserved more respect. This is not anything that we would likely see in 2024, but it truly left its mark on VMAs history as we know it.
Whitney Houston and Mariah Carey wearing Identical Vera Wang Dresses (1998)
Months before a bevy of theatre kids’ lives were changed by the release of the Prince of Egypt soundtrack and the earth-shattering single “When You Believe”, our girls, Whitney and Mariah wanted to have a little fun and poke at everyone thinking they were rivals or as Mariah said on Oprah the public was “dramaticking.” It was a different era in which the public could not fathom that these two vocal titans would get along - we need to pit them against one another. Imagine? Two of our greatest Divas being Friends? The National Enquirer and Star magazine of 1998 could never!
If you don’t already know that Whitney and Mariah are two of our most underrated comedic legends, I will refer you to both Twitter and Fire Island where you will find every single meme/interview clip to prove it to you. However, it’s no shock to me that they were able to both send the audience into a tailspin and make us cackle with their perfect timing in removing the bottoms of their dresses after they noted they were supposed to each be wearing custom dresses and showed up to the podium matching. I know that Dua Lipa and Megan thee Stallion recreated this moment in recent years, but nothing will come close to this original moment and it truly makes you realize just how good we had it when Mariah and Whitney were both at their peak.
Beyoncé performing “Ring the Alarm” (2006)
If you have ever spent a pre-game or a late night in with me, there is an 86% chance that I have shown you this specific VMAs performance. Yes, there are MANY Beyoncé moments to choose from (and probably another important one that we are getting to shortly), but this is the performance that truly cemented Beyoncé as the Beyoncé we love, know, and fear in this current moment.
No one has made a trenchcoat look this good since Ms. Carmen San Diego herself! She commands that stage with LIVE vocals and choreography that defied both gravity and logic. I have watched this performance 999 times and I still have no idea how she and her back-up dancers did not fall backward when they do that backbend! That moment is only heightened by the gear shift sound design beneath her! The moral of this performance is to not cross paths with Bey and unfortunately ALLEGEDLY that could have happened which would then lead to her 2016 Lemonade performance that is also not to be missed!
Lady Gaga performing “Paparazzi” (2009)
In 4 minutes onstage, Lady Gaga in her debut MTV VMA performance cemented herself as an Icon. Period! Rewatching the performance you can see that several people in the audience were confused by what was happening onstage. However, as time has gone on, we could all see the buds of Lady Gaga’s artistry, the way she can truly capture a moment, and suddenly she’s got her foot on the piano showing herself also as an expert musician mid-performance? This performance had such a distinct POV for a young artist on what the fame monster does to us all and if I don’t see this performance hanging in the Smithsonian next to Betsy Ross’ flag in the next 15 years, this is not the America I want to live in!!!
Lady Gaga Meat Dress (2010)
And we can’t talk about Lady Gaga without mentioning THE meat dress. A fashion moment that caused a million people to rethink the charcuterie boards that they were snacking from and ask maybe whether they needed to wear a couple of pepperoni on their salami!!!
Britney Spears performing “I Can’t Get No Satisfaction / Oops! …I Did It Again!” (2000)
When Erika Jayne was talking about being a “Showman” on RHOBH, this is exactly what she was talking about. Britney invented the water cooler! She is the shock! She is the VMAs! She is especially all of that in this performance that has forever been ingrained into our collective memory. She starts this performance by crooning into her headset microphone those low low alto notes of “I Can’t Get No Satisfaction” while sauntering down the stairs in her men’s suit. It has all of the notes of your best senior recital performance when suddenly it is turned all the way up as she tears off her costume bit by bit and launches into “Oops! …I Did It Again!” That bedazzled nude suit and the power that she had underneath it could have singlehandedly changed the results of the 2000 Election if we had let her because she commanded every single viewer in person and at home. I still get chills thinking about her on the edge of the stage when she says “Oooh, I did it again!” and the performance ends. Because she KNEW she did it and she had us and forever will.
Britney performing “I’m a Slave 4 U” - (2001)
See above but with Snakes! (And hives in rehearsal!) Nobody makes eye contact with a camera like Brit!
Kanye interrupting Taylor’s Acceptance Speech for “Best Female Video” - (2009)
I can’t talk about these impactful VMA moments without mentioning the moment even though this moment would be categorized among its worst. I remember exactly where I was when Kanye interrupted Taylor’s speech - I was folding laundry in my on-campus apartment room watching on my tiny little TV and thought I had made up what I had just seen on my TV and had to rush immediately to Twitter to confirm what I saw. And lo and behold that is in fact what had happened.
You can see the millions of emotions that are running through both Beyoncé and Taylor’s faces at this moment - humiliated and mortified by what he had run onstage to do. None of us could have known this moment would still be relevant 15 years later as we have seen the fallout both in the media and musically as it inspired several songs on “Speak Now” and “Reputation”. This is the main reason I’m even mentioning this in this list because tonight’s VMAs marks the 15th anniversary of this moment. It has led many to speculate (mostly me and a million other Swifties in your local circus tent) that tonight could be the night for Taylor to announce Reputation (Taylor’s Version). Part of me is hoping for this, because it would allow Taylor to come full circle on this moment that could have caused her to be defeated and never recover and instead redefined her reputation as we all know it!
Britney, Madonna, Christina Aguilera, and Missy Elliott performing “Like a Virgin” / “Hollywood” - (2003)
I mean, what’s not to love? Christina’s insanely questionable spray tan, the opening notes of “Like a Virgin” as we see Britney slowly revealed underneath her veil, Madonna’s commanding entrance kissing the pop starlets that only grew from her influence. The most underrated part of the performance are the cuts to different musicians in the audience (Not J*stin Timberlake! Please! This isn’t 2001!) - calling back to our girl, Mary J. Blige from earlier who looks absolutely disgusted and confused by the performance while the original Fab Five are just losing their minds. 50 Cent and Vivica A. Fox were dating and went together?! A true time capsule of 2003. It was the kiss heard around the world and lest we forget, Missy was there too! (and it would have been J. Lo had she not been shooting Shall We Dance?)
Beyoncé performing “Love On Top” - (2011)
You already know that we have to wrap this list with THE performance! Bey hitting every single key change! Lady Gaga as Jo Calderone sitting next to Tony Bennett! The mic drop and the bump reveal! The pure joy on Jay-Z’s face with that grin ear to ear! There was nothing more authentic and joyful than this moment.
Now I have certainly worked myself up and cannot WAIT to see what the VMAs have in store tonight. Will Chappell Roan have her Lady Gaga “Paparazzi” moment? Will Katy Perry make us all forget about working with Dr. Luke in her Video Vanguard performance? Will we get an unexpected onstage makeout? Who knows?! That is the beauty and the joy of the VMAs! Happy 40th VMAs!
If you weren’t aware, they were originally taking place on September 10th, and when the Presidential Debate was announced to happen on September 10th, like a love interest in a Jane Austen novel they graciously agreed to not compete and host the VMAs a day later. On 9/11. (Or, like I would like to imagine, we all know there was more Industry back and forth going on behind the scenes making this decision, of which none of us are aware.)