Ahead of the 2019 VMAs and Missy Elliott being honored with an overdue Video Vanguard Award, EW revisits some of our favorite music videos from the visionary rapper.

By Clarkisha Kent
August 22, 2019 at 09:51 PM EDT

Missy Elliott dominated and commanded the attention of the hip hop world and music world at large with her the arrival of her groundbreaking debut (and solo) album Supa Dupa Fly in 1997. Even lovers of all things avant-garde were turning their heads at her futuristic and wonderfully experimental music videos, right down to that iconic “Black Michelin Woman” look. And yet, the prestigious MTV Video Vanguard Award has eluded her grasp much to the chagrin of many music fans…until now.

Rob Loud/WireImage

This year, Elliott will finally be honored with that accolade, making her the first female rapper to receive it. But Elliott’s small yet unimpeachable videography stands as proof that the rapper and songwriter should have acquired the award years ago.

And here are some of our favorites:

7. “Hot Boyz”

This video deserves to be on this list purely because it features greats like Mary J. Blige, Ginuwine, Eve, Timbaland, Lil Mo, and Nas rapping on a motorcycle, and for being one of many collaborations with famed director Hype Williams (behind videos like “Mo’ Money, Mo’ Problems” and recipient of the Vanguard Award in 2006). Directed in a huge arena, the video was not at all shy about employing spectacle, even to the point of having Elliott, Nas, and Eve put the flash in flashy by rapping in front of explosions, colored smoke, and literal flashing lights — all tied together by the fast and creative cuts you would see in an action movie.

6. “Get Ur Freak On”

“Get Ur Freak On” looks like it’s going to be a regular, schemuglar music video with cute and quick opening freeze-frame shots of stars like Nate Dogg, Nicole Wray, Ludacris, Busta Rhymes, Spliff Star, Eve, Master P, Romeo, Timbaland, Ja Rule, and LL Cool J. But then, it quickly says “SIKE” and we find ourselves transported to what looks like a temple, sewer, and/or jungle ruins (or perhaps all three) as Elliott shimmies through it all. The video is intercut with an array of dancers who are not only in well-styled camo, but also dancers who strike an eerie balance between looking like moving statues or creepy jungle dwellers. And in case you think that’s not nonsensical enough, Elliott channels her best Reed Richards (a.k.a. Mister Fantastic) impression by stretching her neck at one point and getting in the camera’s face and later swings from a chandelier. It was madness. It was chaos. And it was Missy.

5. “Work It”

“Work It” ushered in the resurgence of Elliott’s more bizarre and outlandish music videos, particularly after the deaths of longtime collaborator and friend Aaliyah and fellow rapper Lisa “Left Eye” Lopes (who are referenced in the video via airbrushed portraits on Elliott’s jean jacket and car). The video, while repping Elliott’s brand of weird, also served to be one of her funnier videos, with the artist baseball-sliding through a playground at the opening, DJ-ing while covered in bees, zero-gravity dancing, her head superimposed on some smaller person’s body (with a dunce cap), and so much more. The video also featured the first appearance by then-kid dancing prodigy Alyson Stoner. It would later go on to win Video of the Year in 2003 and ranked No. 2 on Billboard’s 2018 ranking of greatest music videos of the 21st century.

4. “She’s A B—h”

“She’s A B—h” can be described as whatever wonderful creation would come forth as a result of combining perhaps the best part of Blade and The Matrix, but making it darker, angrier, and grittier. Celebrating yet another collaboration with the visionary known as Hype Williams, Elliott’s black, bad, and bald protagonist was a revelation here, leaning very hard into Afro-futurist imaginations with electroluminescent lighting, yet also being an inspiration to oft-overlooked black goths everywhere (yes, we exist). And it also managed to do this while re-introducing Elliott as “that b—h” in the music world in a very “who’s gonna check me” way and reclaiming a word that had been historically used to deride and denigrate women for things like our ambition. The video also remains one of the most expensive of all time, clocking in at over $2 million in production costs.

3. “Lose Control”

“Lose Control” remains a favorite because of the masterful way in which it combines the artfully tasteful with the absolutely ridiculous. In yet another Dave Meyers collaboration, Elliott returns with Fatman Scoop and newcomer Ciara to dazzle and confuse and dazzle again. Some of the more iconic imagery in this video features Elliott unearthing herself from the sand before joining a group of dancers, with her head digitally imposed on someone else’s body. It also makes use of more anti-gravity dancing, which at this point has become a favorite of Elliott’s. Ciara and Mötley Crüe’s Tommy Lee hold their own where zero-gravity dancing is concerned as well, with the latter floating humorously over a plank while dancing opposite of Elliott, and the former dancing right before being thrown against a wall. The video was a smash hit, became the most played music video on MTV2 and BET, and the second most played music video in the United States.

2. “Sock It 2 Me”

“Sock It 2 Me” marks the reunion of Missy Elliott and Hype Williams after the duo’s groundbreaking collaboration on “The Rain (Supa Dupa Fly).” Elliott takes us to a planet far away and we witness her and Lil’ Kim (who makes a cameo) in red and white suits reminiscent of the Gmail logo (can we say she predicted it? Mayhaps) and running away from robot monsters. In between cuts of planets and background dancers, Da Brat, who is featured, shows up in a black, yellow, and red space suit and saves them. It’s a pretty stellar nod to video games (like the Mega Man series) that is accompanied by stellar set-pieces, creative shots of Elliott and Da Brat flying around, and references Michael Jackson’s “Smooth Criminal” by featuring the King of Pop’s famous gravity-defying lean. The video is an escapist masterpiece.

1. “The Rain (Supa Dupa Fly)”

This list would not be complete without the inclusion of Elliott’s very first solo music video, the video that started it all, “The Rain (Supa Dupa Fly).” Marking her first collaboration with Hype Williams, this is the video everyone seems to come back to, particularly because it debuts Elliott’s defining and enduring imagery of the black Michelin Man suit. The Michelin look itself remains an important part of Elliott’s career — it was a defiant, provocative, and ingenious way to introduce Elliott as a solo artist to the world and industry, particularly because the industry had not always been kind to fat and plus-sized black women. One of the earliest shots in the video shows Elliott back-first while in the suit and it only gets more imaginative from there. With cameos from Timbaland, Tamara “Taj” Johnson-George from SWV, Yo Yo, Lil’ Kim, Total, 702, Da Brat, Lil’ Cease, and Puff Daddy (now Diddy), the rest of the video showcases perhaps the cleverest usage of the fish eye lens in music video history and is as loud, as colorful, and as bombastic as you’d expect from someone with Elliott’s impeccable taste and range. “The Rain” was nominated for Best Rap Video in 1997 at the VMAs and has gone on to be parodied numerous times (most famously by Chris Rock for his “Champagne” video), but nothing quite captures the perfection of the original.

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