The annual MTV Video Music Awards have been one of pop culture’s biggest nights for decades. Good, bad or ugly, the show has had more than its fair share of headline-making moments since its debut in 1984. Remember when Drake professed his love for Rihanna on stage in 2016? Or Michael Jackson and Lisa Marie Presley’s awkwardly long kiss in 1994? Oh, and need we even mention Lady Gaga’s 2010 meat dress?
Despite its anything-goes reputation, the ceremony has always been a celebration of the year in music. Musical acts across genres are recognized not just for their records and albums, but for the hard work and creativity they put into accompanying visual works. And although going home with a moon person trophy (most notably for video of the year) is surely a goal for nominees, for viewers, it’s the show’s performances that consistently leave people talking.
To celebrate the TV spectacular, we’ve dug back into MTV’s archives to round up the best performances in VMA history. There’s no question that pop megastars including Michael Jackson, Madonna, Britney Spears and Lady Gaga made a strong showing on the tally. Hip-hop heavyweights like Kendrick Lamar, Eminem and Kanye West have also made their mark — especially as the genre grows further into the mainstream. Plus, Video Vanguard recipients from Justin Timberlake to Missy Elliott have proven their superstar statuses with show-stopping medleys.
But who had the most memorable moment of all? Find out where these acts and more rank and relive 23 of the jaw-dropping performances below.
Justin Timberlake, Medley (2013)
The sheer breadth of Timberlake’s catalog is easy to forget, so the singer made sure to remind us during his Video Vanguard performance at the 2013 VMAs. Justin took the stage for over 15 minutes and ran through almost every one of his biggest hits. The best part? A mini *NSYNC reunion — the first in a decade — when his former bandmates joined him on stage for a few ultra-memorable moments. Watch here.
Lady Gaga & Ariana Grande, ‘Chromatica’ Medley (2020)
Welcome to Chromatica. Even at the height of the pandemic, Lady Gaga went all out for her 2020 VMAs performance. Complete with an electronic face mask, Mother Monster took us to her fictional planet for a near-10-minute showcase featuring a handful of hits off her sixth studio album. Of course, sharing the stage with Ariana Grande and her trademark whistle-tones for their Hot 100-topping duet “Rain On Me” was sure to get fans at home on their feet. But her live rendition of “Stupid Love” was a surprising standout: it’s just Gaga’s raw vocals and her brain-shaped piano at center stage, until a pause for a heartfelt speech turns the set back into the dance-ready ball that Chromatica is all about. Watch here.
Shakira, Medley
Shakira brought some of the magic of her 2020 Super Bowl halftime set to the VMAs in 2023, where she was honored as the year’s video vanguard award recipient. Opening with a ferocious “She Wolf,” the Colombian star transitioned into more recent Spanish-language hits (“TQG,” her Karol G collab, and “Te Felicito,” her Rawu Alejandro duet) over the course a fiery, hip-shaking medley. She shook it in the middle of a thumping drum circle, got drenched in pouring (stage) rain during “Hips Don’t Lie” and shared the spotlight with a very enthusiastic audience member who seemed to know all the words to her Bizarrap collab “Bzrp Music Sessions, Vol. 53” during that smash. Watch it here.
Jennifer Lopez, Medley (2018)
Jenny took us around the block and beyond for her 2018 VMAs Video Vanguard Award performance. In a career-spanning tour de force filled with quick changes and dance breaks, the singer performed all her biggest hits — from her groovy 1999 single “Waiting for Tonight” to her 2002 Hot 100 chart-topper “All I Have” to her then-current Spanish number “Dinero.” Both Ja Rule and DJ Khaled made guest appearances to pay homage to her storied career, as her at-the-time beau A.Rod watched awestruck from the crowd. Watch here.
Britney Spears, “Oops! … I Did It Again” (2000)
Spears has had many show-stopping VMA moments over the years, but the pop princess’ 2000 performance remains one of her most memorable. After kicking things off with her cover of the Rolling Stones’ “(I Can’t Get No) Satisfaction,” Spears proceeded to strip down to a nude bikini top and hip-hugging pants, shake out her blonde hair and dance her heart out, growing from a precocious teen into a sexy, grown-ass woman right before our eyes. Watch here.
Rihanna, “Disturbia”/ “Seven Nation Army” (2008)
Subtly pairing the beat from the White Stripes’ “Seven Nation Army” with her own haunting pop, Rihanna kicked off the 2008 VMAs with “Disturbia.” Naturally, an onslaught of “Thriller”-esque dance-zombies took the stage and rounded out the eerie gig.
Madonna, “Like a Virgin” (1984)
Already a huge star when she took the stage, Madonna went supernova at the inaugural VMAs and set the bar for every artist in her wake. The imagery from that performance — the wedding dress, the “Boy Toy” belt, writhing on the floor — became so iconic that Madonna herself repeated it with Britney Spears and Christina Aguilera during her also-memorable 2003 performance. Watch here.
P!nk, Medley (2017)
Ahead of accepting the Video Vanguard award in 2017, P!nk undoubtedly solidified her rockstar status with a medley of her most iconic songs. Kicking off her set in the best way possible with her 2001 hit “Get The Party Started,” the singer paid homage to her roots and kept the crowd captivated the whole way through. Watch here.
Kendrick Lamar, “DNA.” / “Humble.” (2017)
Kendrick Lamar brought the heat (literally) to his 2017 VMAs opener. Taking a stand against police brutality, the rapper performed two hits off his Pulitzer Prize-winning album DAMN. as ninjas scaled a fiery wall and a swordsman performed fancy footwork while fully engulfed in flames. Watch here.
Taylor Swift, “You Belong With Me” (2009)
Country gal Taylor Swift got a taste of the big city life at the 2009 VMAs, performing “You Belong With Me” on the uptown F train before emerging from the subway and climbing on top of a taxi. Swift was riding high from the innovative performance, until Kanye West proceeded to bring her down a peg later that night with his “Imma let you finish…” rant. Watch here.
Kanye West, “Runaway” (2010)
It was a performance that could only come from the mind of Yeezy. Alone on a black and white stage, West wore a vibrant red suit and played DJ before launching into his huge self-referential hit about toasting the douchebags and a–holes. Ballerina dancers joined him onstage briefly, but then Yeezy was left alone to shine. Just how he likes it. Watch here.
Chris Brown & Rihanna, “Wall To Wall”/ “Umbrella”/ “Kiss Kiss” (2007)
The carnival-esque Charlie Chaplin routine to “Wall To Wall” that opened Chris Brown’s nearly six minutes on stage performing at the 2007 VMAs was just the beginning. Soon he was leaping across the seven mini-stages in the audience. But things truly kicked into high gear when Rihanna, in a sexy black ensemble, joined him for an interlude of her hit “Umbrella.” Lest he let her steal the show, he grooved into full-on classic Michael Jackson mode with “Billie Jean”-inspired moves before breaking into his own “Kiss Kiss.”
Madonna, Britney Spears, Christina Aguilera & Missy Elliott – “Like A Virgin” / “Hollywood” (2003)
When four powerhouse female acts unite, of course magic happens. Donning wedding dresses reminiscent of Madonna’s game-changing 1984 VMAs performance, Xtina and Brit cover “Like A Virgin” before the Queen of Pop herself emerges in all black to a well-deserved standing ovation. And we can’t forget the double smooch situation that happens before Missy Elliott turns up. Watch here.
As memorable as it is meaningful, this Diddy tribute to the Notorious B.I.G. got plenty of big names to participate: Biggie’s widow, Faith Evans, R&B group 112 and Sting, who stopped by to contribute live vocals to The Police’s “Every Breath You Take” sample. It remains one of hip-hop’s most touching and tender award show moments. Watch here.
Eminem, “The Real Slim Shady”/ “The Way I Am” (2000)
Performing amidst a sea of Eminem lookalikes, Marshall Mathers made his point loud and clear at the 2000 VMAs: He is and will always be the Real Slim Shady. In an image etched into our minds, Em led his the imitators through Radio City, later busting right into “The Way I Am.” Watch here.
Beyoncé, “Love on Top” (2011)
When Beyonce strutted on stage at the 2011 VMAs in her tux-inspired suit and belted out “I want you to feel the love growing inside of me,” the internet was freshly alight with reports that she was pregnant following a glowing walk down the red carpet. Her energetic performance of “Love on Top” keyed into the news that she and Jay-Z were expecting, and when she dropped the mic, unbuttoned her jacket, winked and rubbed her belly with a big smile, viewers everywhere were captivated. Watch here.
Missy Elliott, Medley (2019)
There’s no better act to help the crowd get their freak on than Missy Elliott. The 2019 Vanguard award honoree lit up the stage with a medley of hits, from “Lose Control” to her latest release at the time, “Throw It Back.” The standout set was filled with plenty of epic surprises — including a CGI UFO and a spotlight dance moment for Alyson Stoner, who hit the stage 17 years after making a splash in Elliott’s “Work It” video. Watch here.
Britney Spears, “I’m A Slave 4 U” (2001)
All sexy and grown-up, Britney busted out in a big way at the 2001 VMAs, channeling the sauna vibe of her “I’m A Slave 4 U” video with a jungle-themed performance. But the real star of the show was the albino python that she wore around her neck like a sexy accessory. Watch here.
Lady Gaga, “Paparazzi” (2009)
In what may be Gaga’s best awards show performance ever, Mother Monster riffed on her “Paparazzi” video with a treatment that was equally as epic. Instead of the video’s paralyzing fall, Gaga takes one in the chest, dripping faux blood on stage and being strung up from the ceiling. Even for Gaga, the moment was gasp-worthy. Watch here.
Beyoncé, ‘Lemonade’ Medley (2016)
When it comes to artists who know how to put on a show, there’s no doubt that Beyoncé is a top contender. Her 15-minute triumph featuring much of her Lemonade album was a masterpiece on par with a big-budget stadium show — complete with a camera smashing moment and backup dancers that showed up with all the energy the history-making 2016 album deserves. Watch here.
Bon Jovi, “Livin’ On a Prayer”/ “Wanted Dead or Alive” (1989)
In a performance largely credited with inspiring MTV’s massively popular Unplugged series, Bon Jovi brought its hair/pop-metal down to earth for a riveting acoustic jam session. Jon snapped and strummed along with Richie Sambora’s double guitar, as the two brought down the house with two of the band’s biggest hits, portrayed this time in a more modest light. Watch here.
Michael Jackson, Medley (1995)
Michael Jackson proved, yet again, just why he was the King of Pop at the ’95 show. Not only did he give MTV viewers a 15-minute medley of many of his biggest hits (including “Beat It,” “Billie Jean,” “Black or White,” “The Way You Make Me Feel” and more), but he did it with on-stage costume changes, moonwalking, Slash shredding on guitar, dance-fighting and enough crotch-grabbing for the whole of the ’90s. Such was the awesome power of this spectacular MJ performance, which set the standard for today’s Video Vanguard performances. Watch here.
Madonna, “Vogue” (1990)
Talk about a cross-century mashup: Madonna and her company of dancers, clad in 18th century Marie Antoinette garb, taught the world how to vogue, a performance style popularized in underground LGBTQ dance clubs in ’80s New York City. Cue one incredibly animated pants-less dancer, and VMAs magic is made. Watch here.
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