Since the mid-’80s, when acts like Run D.M.C. were breaking down barriers that kept rap music videos from appearing on national, mainstream outlets like MTV, releasing a strong visual to complement a song became an important part of an artist’s success. As the ’90s arrived, artists and directors alike upped the ante and budget, doing away with minimalism. Their intentions were to blow the minds of viewers and help build awareness of the music. Among the artists who took particular pride in pushing the envelope of cinematography was Missy Elliott. She became a vanguard for inventive and futuristic clips, which reflected her personality and proved to be events in and of themselves. While videos for songs like “Get Ur Freak On,” “Work It” and “Lose Control” would all be hailed as influential and captivating, Missy’s road to being a music video trailblazer began with “The Rain (Supa Dupa Fly),” her debut single as a solo artist.
The Hype Williams-directed video would be unveiled in summer of 1997 and instantly become a hit with viewers, who were equally intrigued as they were entertained by Missy’s quirky tendencies. She appeared in a humongous black hefty bag, a bike helmet that doubled as sunglasses, and on a fairytale-like hill while donning a wig. “The Rain (Supa Dupa Fly)” single and music video influenced Supa Dupa Fly‘s ascent to platinum status and stamped the visual as a ’90s pop culture staple. While Missy’s performance may have gotten most of the attention, the music video boasted a bevy of guest appearances from some of the most notable hip-hop and R&B artists of that time, making “The Rain (Supa Dupa Fly)” a cultural hallmark.
In celebration of her debut studio album’s 20th Anniversary, we dissect “The Rain” and rank all of the cameos in the video, from least to most memorable.
9. Taj of SWV
Tamara “Taj” Johnson-George, a member of iconic ‘90s R&B trio SWV, is the first guest to appear in the accompanying visual to Missy Elliott’s debut single. While gearing up for the release of SWV’s third studio album, Release Some Tension, Taj, who rocked a black Fubu top and a chain with a pendant and appeared in place of Coko. Although the lead singer was name dropped in the song, she does not appear in the video. Couple that with her cameo being a brief one, and Taj’s placement on this list is self-explanatory.
8. Lil Cease
The Junior M.A.F.I.A. member is one of many faces viewers catch a glimpse of while watching the Hype Williams-directed visual. Appearing alongside his groupmate, Lil Kim, he sports a black tee and durag, keeping it very Brooklyn and adding a little Bed-Stuy flavor to the proceedings.
One of two R&B trios to make cameos in “The Rain (Supa Dupa Fly)” is 702, who struck gold with their debut album No Doubt the previous year. The singers can be seen staying true to their around-the-way girl image and exuding an equal mix of sass and beauty. With Missy Elliott having contributed a verse to the Las Vegas natives’ hit single “Steelo,” and appearing in the accompanying music video, 702 repaid the favor with a show of support and became a part of one of the most original music videos of all time.
One of the most dominant figures in ‘90s rap reached the pinnacle of the music world but endured tragedy when The Notorious B.I.G. – the flagship artist of Bad Boy Records – was gunned down in March 1997 while in Los Angeles. However, Puffy bounced back in a big way with his debut album as an artist, No Way Out, and shook up the music world a week after Missy Elliott’s “The Rain (Supa Dupa Fly)” was released. Having worked with Missy on multiple occasions over the previous two years, Puff appears dressed down in a black leather jacket, white tee, blue jeans, a Pittsburgh Pirates cap and shades.
West Coast rapper Yo-Yo, most known for her affiliation with Ice Cube and her hit single “You Can’t Play with My Yo-Yo,” makes what is arguably the most memorable cameo of her career in Missy Elliott’s “The Rain” music video. Rocking black athletic gear with white trimming while sporting a few jewels for good measure, the artist was one of three artists pops up in the video twice, first basking in the glory of Missy paying homage in a lyric, then showing off a few dance moves.
4. Da Brat
Prior to Missy and Lil Kim getting their platinum plaques, Da Brat made history as the first female rapper to achieve that feat with her debut album Funkdafied, which touched down in 1994. Riding high off of her gold-selling album, Anuthatantrum, the Chicago area native shows some solidarity while making an appearance on the behalf of So So Def and literally get rowdy, throws a tantrum and rips off her platinum denim jacket. Da Brat’s presence served as a central figure in one of the most unforgettable scenes in Missy’s definitive clip.
3. Lil Kim
Ascending as a rap diva with her seismic debut album, Hard Core, Lil Kim’s reign would carry on into 1997, with singles like “Crush on You” and more keeping her name and face front and center. Scoring another guest feature with her verse on the Supa Dupa Fly album cut “Hit Em Wit Da Hee,” the Queen B***h lends her sex appeal and charisma to “The Rain,” sharing a scene with Cease-A-Leo, before coyly staring at viewers in a white blouse, Chanel suspenders, red leather pants and designer shades.
Missy Elliott’s partner from the beginning of her career has been Timothy Mosley, better known as producer Timbaland. The two teamed up and transcended their backyard of Virginia as their sound impacted and influenced the world. Being that “The Rain (Supa Dupa Fly),” which was produced by Timbaland, it was only right that the duos enjoy having the spotlight to themselves and a get a bit of face-time to themselves. From riding in a Hummer with Missy to imitating a plane, Timbo rocks a blue designer jacket, black tee and designer shades, and takes a page from Puffy’s book and is all up in the camera during Hype Williams-directed visual.
Of the numerous artists and groups that are seen in Missy Elliott’s music video, the participants that displayed the most flair and personality were Bad Boy R&B group Total, who completely stole the show with their carefree antics. After gaining recognition for their hit single “Can’t You See” and making guest appearances alongside The Notorious B.I.G. and LL Cool J, Kima, Keisha and Pam became one of the hottest R&B acts in the mid-‘90s. With their sensuous, but edgy image in tow, the singers dance around in multiple scenes of Missy’s “The Rain” video. In fact, they appear in the most scenes, with the final showing the lower part of Keisha’s face defying the laws of gravity. Thus, making it one hell of a punctuation to a timeless video that is still entertaining to this day.