Britney SpearsChristina AguileraJessica SimpsonMandy Moore
The pop star performed "Slave 4 U" in this ~jungle-themed~ bikini in 2001.
Michael JacksonJustin BieberJustin TimberlakeChris Brown
The NSYNC star made his solo debut on the VMAs stage in this outfit in 2002.
Tom Green and Drew BarrymoreTommy Lee and Pamela AndersonAndy Dick and Dita Von TeeseMarilyn Manson and Rose McGowan
Madonna and Rose McGowan!
The rocker and actress shocked everyone at the 1998 VMAs.
Miley CyrusSelena GomezBritney SpearsJessie J
The Disney star made headlines in 2013 with a twerktastic performance of her hit "We Can't Stop."
Lady GagaNicki MinajKeshaRobyn
The rapper walked the red carpet in the over-the-top Harajuku-inspired creation in 2011.
Mike Will Made It and Miley CyrusJay Z and BeyoncéChris Brown and RihannaPuffy and Jennifer Lopez
Puffy and Jennifer Lopez!
The power couple wore matching white and denim to the 2000 VMAs.
The rapper wore this breast-baring number in 1999.
MadonnaCyndi LauperLady GagaCourtney Love
The Artpop star wore a dress made of meat to accept the trophy for Video Of The Year in 2010.
Christina AguileraBeyoncéJanet JacksonAlicia Keys
The **flawless star wore a sequined jumpsuit to perform "Love On Top" (and announce her pregnancy with Blue Ivy!) in 2011.
MadonnaBritney SpearsChristina AguileraPink
Madge originally rocked the boytoy bride look in 1984 — decades before Britney and Christina revived it.
Riff Raff and Katy PerryJustin Timberlake and Britney SpearsJustin Bieber and Selena GomezChad Kroeger and Avril Lavigne
Riff Raff and Katy Perry!
The odd couple paid homage to Britney and Justin's iconic denim outfits at the 2014 VMAs.
Lauryn HillMissy ElliottMacy GrayKelis
At the 2001 VMAs, the soul singer made sure everyone knew her album release date.
FergieShirley MansonLisa "Left Eye" LopesGwen Stefani
The No Doubt frontwoman wore a blue bikini top rocked every late '90s trend on the red carpet of the 1998 VMAs.
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