An Illustrated Guide to the Best Sneaker Moments in VMA History

A look back at the sneakers that defined the MTV Video Music Awards.


Illustrations by JSNJAY

MTV’s Video Music Awards may not carry the musical clout of the Grammys, but they’ve long been the awards show of choice for the younger generation. Unsurprisingly, artists have used the show as a platform to showcase the style just as much as their artistry.

The channel may be barely even associated with music anymore, as much as it is with reality TV, yet the annual awards event rolls on—this year marks the 34th annual show. But before you watch performances by Travis Scott and Nicki Minaj, or see Jennifer Lopez honored with the Video Vanguard Award, take a look at an illustrated guide to the most important sneaker moments in the history of the VMAs.


Name: Canibus
Shoe: Nike Total Air Foamposite Max
Year: 1998
Performance: "Ghetto Superstar" 

If you’re wondering what Canibus may have possibly been doing at any VMA awards show, you’re not alone. For a brief period of time, he appeared poised for success following his debut album, “Can-I-Bus.” The album featured multiple production credits by Wyclef Jean, which is ultimately what landed him on the awards show.

Canibus was featured on a performance of Pras’ “Ghetto Superstar” along with Wyclef, ODB, and Mya. He made the most of his time on stage, twice proclaiming “Canibus is the man” during his 20-second intro to the song. As forgettable as his performance was, his outfit actually made a mark on VMA history. The rapper hit the stage wearing a baggy suit, no shirt, and with his body painted entirely in metallic silver with his “C” logo displayed on his face. And his sneakers? The only metallic silver shoe that possibly matched in the autumn of 1998–the Nike Total Air Foamposite Max.

Canibus would go on to feud with Wyclef shortly thereafter, blaming him for the relative failure of “Can-I-Bus.” He unsurprisingly never made it back to the VMAs, but thanks to his fashion choices that night, it was an appearance worth remembering.


Name: Eminem
Shoe: Air Jordan 4 Retro "Cement"
Year: 1999
Performance: "My Name Is/Guilty Conscious/Nuthin But a ‘G’ Thang" 

It would have been easy to write Eminem off as a novelty act in 1999. His first hit that earned him multiple VMA nominations featured a heavy dose of comedy. And, oh yeah, the color of his skin didn’t exactly coincide with the norm for his genre of music.

But a powerful co-sign from Dr. Dre hinted to the fact that there was more to this artist that it appeared on paper. That relationship was further established during the VMAs that year, when Em opened a performance of “My Name Is” followed by teaming up with Dre for live rendition of their follow-up hit “Guilty Conscious.” Em even stuck around to do backups for Snoop and Dre during “Nuthin’ But a ‘G’ Thang,” further cementing his status is an artist to watch.

The highlight of his performance was the light up Nike sweatshirt that flashed “ROLE MODEL,” but his sneaker highlight was the shoe he wore while accepting his Best New Artist Award–the just-retroed White/Cement Air Jordan 4. We had no idea at the time, but this was the first in what would become long-term association of Eminem and Jordan Brand.


Name: Jay-Z
Shoe: Air Jordan 5 Retro "Fire Red"
Year: 2001
Performance: "Izzo (H.O.V.A.)" 

When it comes to sneakers, few appearances in VMA history have had as much heat on the same stage as Jay Z’s performance of “Izzo (H.O.V.A.).”

The year 2001 featured some elite-level Air Jordan retros, and most of them were present during the song. Hov’s performance was opened up by ballers decked in Chicago Bulls shorts and tees dribbling around the stage in sneakers like the “Banned” 1s and Black/Cement 3s. A ball was passed into the crowd and caught by Jay-Z who then hit the stage (flanked by back-up dancers wearing black and red Chucks) in MJ’s number-23 jersey, baggy denim shorts, and the prior year’s release of the White/Black/Fire Red 5s. Even the kids that joined in to dance during the song’s close wore retro Jordan heat.

Hov was only up for one award that year–Best Rap Video for “I Just Wanna Love U (Give It 2 Me),” but lost out to Nelly’s “Ride wit Me.” And pop culture best remembers the 2001 VMAs for Britney Spears’ “I’m a Slave 4 U” performance, holding an albino python. When it comes to sneakers though, Jay Z was the clear winner of the night.


Name: Pharrell Williams
Shoe: BAPE Roadsta
Year: 2006
Performance: "Money Maker" 

Pharrell Williams is responsible for producing a ton of music to be featured on the VMAs but has actually only performed on the show a handful of times. He did “Freedom” solo in 2015 and a medley with P. Diddy in 2002. But his most memorable came in 2006 alongside Ludacris and the Pussycat Dolls for a performance of “Money Maker.”

While Luda sported an all-over money print hoody and heavily embroidered denim–a style you may have seen Skateboard P wearing in the past, Pharrell was already on to the next one with a cleaner look from his recently launched BBC label. There was still plenty of bling though, courtesy of his multiple mult-color chains and metallic Bape Roadstas.

Williams, who arrived at the event with Bape founder and BBC-partner Nigo (wearing a matching outfit), was largely responsible for popularizing the Japanese brand to in the States. Always at the forefront of style, Williams has constantly evolved in the years since and currently is heavily involved with his own adidas line, but it was only fitting that his biggest VMA performance came while wearing what’s best known as his signature look.


Name: Kanye West
Shoe: Nike Air Yeezy 2 "Platinum"
Year: 2011
Performance: "Otis" 

It will be hard for Kanye West to ever live down the 2009 “Taylor Swift Incident” when it comes to his association with the VMAs, but by 2011, he was once again all over the show for the right reasons.

West received seven VMA nominations that year including Best Male Video and Best Hip-Hop Video for “All of the Lights,” and Best Collaboration with Katy Perry, which they won for “E.T.” Musically, West had moved on to Watch the Throne by the time of the award show, which was reflected in his performance.

When West took the stage alongside Jay Z to perform their hit “Otis,” there was no surprise when it came to the Ye’s footwear. It was heavily anticipated that West would debut his new Nike model, which we’d previously only seen glimpses of. He didn’t let us down, rocking the “Pure Platinum” Air Yeezy 2 for the world to see. It would be almost a full year before the Yeezy 2 would actually drop at retail, but that night helped take the frenzy around West sneaker lines to another level.