The Best VMAs Team-Ups of All Time

Kevin Mazur/WireImage
Rihanna and Drake walk offstage during the 2016 MTV Video Music Awards at Madison Square Garden on Aug. 28, 2016 in New York City. 

You can count on the VMAs to deliver headline-worthy moments every year. From The Kiss seen 'round the world in 2003 to Sting teaming up with Puff Daddy after the Notorious B.I.G.'s death, these are the mash-up appearances that make us tune in year after year.

2003: Madonna, Britney Spears, Christina Aguilera & Missy Elliott

In an era before events of, well, consequence dominated the news cycle, the world was set ablaze by what’s simply known today as (gasp!) ‘The Kiss.’ In a team-up for the ages, three of the biggest pop divas took the stage at the 2003 Video Music Awards to shake everyone to their core, and shook they were. Sure, we all know that Madonna planted a smooch on Britney Spears (that’s the shot that landed on the front page of every newspaper, after all), but after an errant camera flashes to Spears ex-boyfriend Justin Timberlake (reaction shot!), we cut back to Madonna placing a peck Christina Aguilera’s lips as well. It was a performance Madonna took with intense seriousness, with Spears' manager Larry Rudolph later explaining to Billboard: "Madonna had been very, very, very rigid about the rehearsals. She was telling Britney and I every day, 'Be here tomorrow at 10 O'clock.’ She would never address me by name, she would just say, 'You make sure Britney's here tomorrow at 10 o'clock.’” Lost in the madness? A wild cameo courtesy Missy Elliott performing her smash “Work It,” which would win the Moonman for Video of the Year later that night.

2014: Ariana Grande, Nicki Minaj, Jessie J

What do you get when you team up three of the dopest divas in the damn industry performing a bevy of bona fide beautiful bops? Solidifying her status as a stupendous superstar, Ariana Grande graces our presence first in this 2014 performance, strutting and singing her signature “Break Free,” then ceding the stage to none other than Nicki Minaj and her amazingly awesome “Anaconda” while wallowing through a woeful wardrobe malfunction. The entire extremely entertaining extravaganza comes to a cool and crazy climax when Jessie J joins the two and the terrific trio treats the audience to a bangin’ version of “Bang Bang,” which was released mere weeks before. Ladies and gentlemen, this is pure pop perfection.

1997: Puff Daddy, Faith Evans, 112, Mase, Sting

In light of the tragic death of the Notorious B.I.G. that March, there was only one way to honor the late hip-hop icon -- by opening up that September's Video Music Awards with a tribute that saw clips of Biggie complemented by a spirited performance of “I’ll Be Missing You.” With everyone dressed in stark white and a choir thrown in for good measure, it was a perfect tribute that combined top tier artists from multiple genres to honor the legend. R.I.P. Biggie.

2013: Miley Cyrus & Robin Thicke

Exactly 10 years after the 2003 lovefest, Miley Cyrus took the 2013 VMA stage to shock the nation all over again -- making Madonna’s kiss seem as innocent as an episode of Paw Patrol. Catapulting twerking into the national vernacular, Cyrus crooned “We Can’t Stop” before Thicke appeared to launch into his smash “Blurred Lines,” which was the No. 1 song on the Hot 100 at the time. Perhaps unsurprisingly, the whole thing became one of the most tweeted moments of all time, and helped Cyrus reach a new level and effectively shake her Hannah Montana image for good. It wasn’t without cost, however. "In the beginning, it was kind of like saying, '[Screw] you. Girls should be able to have this freedom or whatever,”’ she later explained. “But it got to a point where I did feel sexualized."

2009: JAY-Z & Alicia Keys

Grab a bagel, hop in a yellow cab and ignore that smell that’s wafting through the streets: You’re in New York, baby! There was no better duo to close out the 2009 Video Music Awards at Radio City than JAY-Z and Alicia Keys in a debut performance of their instantly iconic “Empire State of Mind.” Starting off with Hov in the bowels of Radio City before ascending to its famous stage like a hip-hop Jesus, the song is a perfect encapsulation of what makes the Big Apple so damn great. It’s such a legendary performance that it makes you almost forget a bizarre spur-of-the-moment cameo by rapper Lil Mama during the song’s, and show’s, finale.

1999: Britney Spears & *NSYNC

At the height of the teen pop explosion, the Kings and Queen of the genre appeared together in a performance any school age youngster of 1999 will remember forever. Opening up on a classroom set full of chatty backup dancer ‘students,’ Spears takes the stage by announcing her presence with “My loneliness is killing me…,” the iconic first words of her career-maker “...Baby One More Time.” Cue *NSYNC, with a plethora of highly-choreographed dance moves set to a soundtrack of sound effects (that grunt!) and beats. (Notably, both Spears and the boys would later lose out on the Moonman for Best Pop Video to Ricky Martin’s “Livin’ La Vida Loca.”)

2002: Jimmy Fallon, Fallon’s Impressions, James Brown

Long before Jimmy Fallon was the superstar host of NBC’s The Tonight Show, he was a fledgling star on Saturday Night Live. Asked by MTV to host the 2002 VMAs after a spirited turn co-hosting their Movie Awards with Natalie Portman, Fallon took the reigns of the VMAs and opened with a wild 10-minute opus of musical impressions (including Avril Lavigne and Dave Matthews). The cherry on top of the opening, however, was a truly surprising cameo by none other than James Brown, with the duo crooning through Brown’s 1970 hit single “Get Up (I Feel Like Being a) Sex Machine.” Generations collided and audiences ate it up.

2017: Drake & Rihanna

Drizzy, meet Ri. Okay, so it wasn’t a performance but watching the biggest male artist in music give the Michael Jackson Video Vanguard Award to the biggest female artist in music turned into a new classic moment in the long history of the show. With the two exquisitely dressed and October’s Very Own speaking from the heart, Rihanna was full of emotion. “What’s most impressive is some artists have to play a character have to achieve success or downplay their own natural instincts to blend in,” said Drake as Rihanna beamed nearby. “She succeeds by doing what no one in this industry does, which is being herself.” Aww.

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