The Motown legend was already on a trailblazing career trajectory after breaking off from the Jackson 5 quintet to embark on a solo career. In 1993, MJ rewrote all the rules when he dropped his 14-minute theatrical spectacle for the eponymous lead single off his Thriller album. That video broke boundaries and propelled him to the upper echelons of the pop stratosphere.

The late King of Pop's irrefutable mark on the music landscape was solidified in the pop culture zeitgeist when the Vanguard Award was renamed to the Michael Jackson Video Vanguard Award seven years after its inception in honor of his record-breaking, barrier-shattering career.

Coming up in the footsteps of the King of Pop is a tough act to follow, but Miss Janet did exactly that two years later. Fresh off the chart-smashing successful debut of her critically acclaimed Rhythm Nation album, Janet made history as the youngest artist to be honored by MTV with the Vanguard award.

At a mere 24 years of age, the "Rhythm Nation" icon beat Madonna’s previous record of 28-years-old by four years. The pop diva was also the first Black female artist to receive the iconic Moon Man.

LL Cool J might be better known as a host and television personality rather than a recording artist these days. But before hip-hop went mainstream, the East Coast legend was one of the pioneers that elevated rap from its underground roots.

Before Nas and Jay-Z, LL Cool J put New York’s rap scene on the map. The Queens native cranked out a number of hits throughout his career that should be in everyone’s list of Hip-Hop’s Greatest Songs. Twelve years after his introduction, LL was recognized for his impact on hip-hop at the 1997 Video Music Awards.

It wouldn’t be 17 years until another Black artist would be bestowed with MTV’s highest accolade, and it would be none other than R&B’s reigning royalty, Beyoncé Knowles-Carter, in 2014. The Houston-native revived high-concept music videos as an art form with the release of her visual album, Lemonade.

Queen Bey fully lived up to her fan-bestowed moniker as she delivered a vocally flawless, showstopping medley of tracks from her self-titled album for 16 minutes straight. Her performance still stands as one of the best VMA performances ever.

The moment was capped when a then two-year-old Blue Ivy stole all of our hearts when she presented Bey her award alongside Jay-Z. The monumental night bumped Bey to one of the most decorated artists in MTV’s history. She currently holds the crown for the highest amount of VMAs. In 2016, the 37-year-old surpassed Madonna to hold the title after she took home eight Moonmen at the 33rd VMAs show, bringing her career total to 26 VMAs.

The Chicago legend had the whole world shocked when none other than country-pop princess Taylor Swift stepped on stage to present Kanye with his Vanguard Award. Kanye’s turn in the spotlight was supposed to be a point of reconciliation between the two, but history has since taught us otherwise.

There’s too many moments from mind-boggling occasion that will live down in the banals of pop culture’s history, but nothing takes the cake more than when Kanye spontaneously announced that he was running for president in 2020 at the end of his 13-minute speech.

Unlike her predecessors, Barbadian beauty, fashion and music maven Rihanna didn’t settle for just one performance when it was her time to join the ranks of music’s greatest at the 2016 VMAs. RiRi showed the world that nobody can do it like she does. The fashion chameleon paraded across the stage on four different occasions serving lewks, choreography and acapella vocals. 

Mary J. Blige was tapped to commemorate RiRi’s illustrious career, which would come full circle when Rihanna paid her respects similarly at the 2019 BET Awards.

As one of hip-hop’s progenitors, Missy has blessed the culture tenfold with a litany of wildy innovative and brilliant visuals that has in turn birthed an entire generation of artists inspired by her work. 

On Monday night (Aug. 26), the Virginia native proved yet again why she's an icon and more than deserving of MTV’s highest honor after being overlooked for years. Missy had us all ready to work it with a supa dupa fly throwback medley of her greatest hits that had the entire crowd losing control as she brought her music videos to life with insane and trippy visual effects that took us into the world of her Misdemeanor alter ego.

The momentous achievement marked another landmark moment for hip-hop: Missy is the first female rapper to ever win the Video Vanguard Award.

Who are some other acts you would like to see join the VMAs Hall Of Fame?