A ranking of Mariah Carey's greatest MTV VMAs moments ahead of this Sunday's broadcast

The 2025 recipient of the Video Vanguard Award at the MTV VMAs this weekend will be the one and only Mariah Carey. The award has been a part of VMA history since it was first awarded to The Beatles, Richard Lester, and David Bowie during the first telecast in 1984 and subsequent honorees include Michael Jackson, Madonna, Janet Jackson, Britney Spears, Beyoncé, Rihanna and more. Mimi being a recipient is a no-brainer, as in recent years she has been on the receiving end of multiple “Icon” or “Legend” awards at various award shows. Plus, she has given us countless iconic music videos over the years like “Heartbreaker”, “Honey”, “Touch My Body”, “Obsessed” and more. What’s shocking however is that up until this very honour, she has not won a single VMA, making this one her very first.

Mariah is performing a medley of her hits at the event, marking her first VMA appearance in 20 years. All of this of course is leading up to the release of her new album Here For It All which drops September 26th. She’s been hot on the promo trail recently, even making a guest appearance on Kai Cenat’s livestream earlier this week in an effort to spread the word of the new album to a younger audience, and I respect it! The first single from the project “Type Dangerous” also earned her a nomination for Best R&B Video, so there’s a good chance that Sunday’s telecast will be one for all the lambs. In honour of MTV finally giving Mariah the flowers that she so rightfully deserves, let’s take a look back at her five VMA appearances over the years.

5. Presenting “Best Group Video”: 1996 MTV VMAS (September 4th 1996)

Mariah’s 1996 VMA moment was short and sweet, yet still pivotal in her eventual transition into the butterfly we now know. Mimi presented the award for Best Group Video to the Foo Fighters and even made a Dennis Rodman dress joke on stage. Tell me it’s 1996 without telling me it’s 1996 lol. Wearing a short chocolate brown dress and knee-high black boots, this is one of the first instances in Mariah’s career where we see her having fun with fashion, and for Mimi that means skin and cleavage. She was still married to Tommy Mottola at this point, and if you’ve read her memoir The Meaning of Mariah Carey then you know he wouldn’t allow her to wear any revealing garments so the fact that she was actually showing some skin here was major for her, and is telling of the eventual fashion choices she would make in future years. This event came towards the end of that marriage, and she would make her full metamorphosis at the VMAs the following year (which trust me, we will get to). Mariah was only nominated for one award that evening for “One Sweet Day” in the Best R&B Video category (her first-ever nomination believe it or not) and lost to The Fugees “Killing Me Softly”. By September 1996, she was on the tail end of arguably her biggest album Daydream that spawned major hits like “Fantasy”, “Always Be My Baby” and “One Sweet Day” with Boyz II Men so in hindsight it is quite shocking that that was only enough to earn her one nomination. Unfortunately, award shows in the 90s were keener on rewarding artists that were seen as “respected” and while Mariah was selling the most records and earning the most #1 hits, she unfortunately wasn’t seen as a true “artist” in the eyes of the music critics. As far as MTV was concerned, the mid- 90s was a time of grunge and rock bands taking over and the network favored those artists when handing out the Moon Man.

4. “Shake It Off” + “We Belong Together” Performance: 2005 MTV VMAs (August 28th, 2005)

2005 was a magical year for Mariah as she had one of the most successful comebacks in music history with her smash-hit album The Emancipation of Mimi. This came after a relatively rough period for her commercially (even though I will continue to defend Glitter as long as I live). Once “We Belong Together” came out, everything changed and Mariah silenced the haters once again by not only managing to make a comeback but also releasing what would become the biggest (non-Christmas) hit of her career. This feat earned her two VMA nominations that year and a slot performing on the live show, even appearing in print ads leading up to the big day. The 2005 VMAs were held in Miami at the American Airlines Arena and hosted by Diddy (yikes), but Mariah the effervescent diva that she is, instead performed live from the National Hotel in South Beach taking over the rooftop pool in a special on-location performance. Together with Jermaine Dupri and Jadakiss, Mimi performed “Shake It Off’ and remix of “We Belong Together” all while wearing a blue diamond dress, insanely high heels and, of course, barely moving. In case you’re new to Mimi land, our girl will always put a high heel over the ability to move and we are very much encouraging of this. It was during this era that the moving on stage came second to the glamour of it all – the next era of Mariah if you will. She was nominated for both Best R&B Video and Best Female Video which she lost to Alicia Keys and Kelly Clarkson respectively. I love both of those girls but it is f-cking criminal that Mariah once again had the both the biggest album and song of the year and that still wasn’t enough for a win.

3. “Emotions” Performance – 1991 MTV VMAs (September 5th, 1991)

Mariah made her first appearance on the MTV VMA stage in 1991 when she performed “Emotions”, the lead single from her sophomore album of the same name. The song is famous for highlighting those signature whistle tones that made her a household name in the early 90s and was her fifth consecutive #1 hit on the Billboard Hot 100. Mimi wore a puffy white silk shirt (it’s giving Seinfeld), a pair of black hot pants and black tights. She even was snapped chatting with Whoopi Goldberg backstage who was fresh off her Oscar win for Ghost. Horrendous outfit aside, her vocals are the true centerpiece here because wow, just wow. It doesn’t take a genius to recognise that “Emotions” is one of the hardest songs for any singer to sing, period. Mariah writes all her music and it’s almost as if she wrote them in a way that make her literally the only person who can sing them live (and thank God for that). Not only did she deliver the goods, but she also hit her highest note ever recorded thus far during this very performance – a G#7 at the 3:56 mark. For reference, a G#7 is a few keys from the top of a piano, meaning that she literally out sang a damn instrument. This little riff isn’t on the recorded version of the song, making this live performance even more unique to her vocal legacy.

2. The Breakup Dress + Presenting Video Vanguard: 1997 MTV VMAs (September 4th, 1997)

The moment that changed Mariah’s public persona forever, the moment where she finally spread her wings to fly. The 1997 VMAs marked Mariah’s first public appearance since her separation from Tommy Mottola which had been announced to the public a few months prior, in May of that year. She wore her now infamous two-piece black ensemble that the lambs adoringly call her breakup dress. She had also just released the music video to her single “Honey” which was sending shockwaves through the industry as it showed a whole new Mariah both sonically and visually. Mariah was owning a much sexier image and a more urban sound, making a complete departure from the adult contemporary songs that she had become famous for in previous years. She was finally free to make the music she wanted to make and wear the garments she wanted to wear. When she stepped onto that carpet though, she turned more than a few heads wearing a bandeau with small straps and a long skirt with a slit so high that it basically split the skirt in two. Even Mariah herself in her recent Vogue retrospect acknowledges that the slit was a little high. When Mimi herself thinks it’s risqué, you know it’s the real deal – no complaints here as Mariah has always found a way to wear a skimpy outfit in the classiest way possible, lol. This “break-up dress” to me gives total Princess Diana 1994 Serpentine Gallery gala when she stepped out letting Prince Charles know exactly what he was missing out on. Mariah was finally free to be herself and not the caricature that Tommy had designed for commercial consumption and what better event than the biggest night in music to do so? Mariah also presented LL Cool J with the Video Vanguard award that night, making this upcoming 2025 ceremony extra special since now it’s Mariah getting the award and LL is hosting – a full circle moment for our butterfly.

1. Whitney Dress Gag+ Presenting “Best Male Video”: 1998 MTV VMAs (September 10th, 1998)

What’s better than a diva dressed in a custom chocolate brown Vera Wang gown to open the MTV awards? That’s easy – two divas. This ceremony marked the beginning of one of the most iconic press tours in diva history, Mariah Carey and Whitney Houston for their collaboration “When You Believe” from The Prince of Egypt. Up until this point, the two divas had been unfairly pinned against each other in the media, likely due to the fact that they both were powerhouse vocalists and also were both in the elite group of best-selling artists of the decade. The light shade Whitney would throw here and there didn’t help, but it’s Whitney, that’s just how she was and we loved her for it. The two of them coming together was a cosmic eruption in pop culture, and will continue to remain one of the most untouchable collaborations of all-time. Ben Stiller was the host of the 1998 show and introduced the first presenter of the evening as “one of the best singers in the world”, with Whitney appearing onstage. Only to be cut off midway with “Honey” beginning to play in the background as Mariah appeared from the other side of the stage. A literal diva-off, three-year-old me was f-cking gagged – and yes, one of my earliest memories is watching this very award show. This was a few months before Britney Spears burst onto the scene but this little gay boy was already looking up to the queens of the time. Once the ladies realized they were both wearing the same dress, each removed a layer of fabric to reveal two separate dresses in what would become one of the most iconic gags in VMA history. One that has stood the test of time as well and was recently re-created in 2022 by Megan Thee Stallion and Dua Lipa at the Grammy Awards.

Mariah has since told a story or two about the dress having its own police escort and it getting lost in the process, only to end up being delivered moments before the carpet – oh, the drama. The moment was so iconic that everyone all but forgot the actual reason why they were there which was to present the award for Best Male Video which ended up going to Will Smith. No shade to Will, but respectfully, no one cared. The most important part of all of this is that this is when Whitney and Mariah finally put an end to those feud rumours that had been circling the industry since Mariah came out with her first single back in 1990, rumours that Whitney herself had been hoping would finally be put to rest, even though she unconsciously contributed to them, ha. The result is a moment in VMA history shared by two of the most powerful women that music has ever seen. I just love my divas so f-cking much.