Hilary Duff
Let's go back (yes, back to the beginning). The Lizzie McGuire star showed that her appearance was what dreams were made of in 2003.
Jessica Simpson
It simply wouldn't have been a public affair without Jessica Simpson (and her stunning white suit) making an entrance.
Mary Kate Olsen & Ashley Olsen
The Olsen twins weren't just there for a New York minute. In fact, Mary-Kate and Ashley served as presenters for Best Pop Video during that year's ceremony.
Britney Spears & Madonna
Who could forget when Britney Spears and Madonna, as well Madonna and Christina Aguilera, shared onstage kisses during their unforgettable performance? Twenty years later, and the world is still pretty hung up on it.
Carmen Electra & Dave Navarro
Remember when Carmen Electra and Dave Navarro were a couple? In fact, this photo of the then-couple was taken three months before they tied the knot. Alas, the model filed for divorce nearly three years later in 2006.
Justin Timberlake
The "Cry Me a River" performer took home a Moonman that year for Best Male Video. However, his award wasn't the only moment he was in the spotlight. Let's not forget that cameras infamously zoomed in on his reaction after his ex Britney and Madonna shared that kiss during their performance.
Avril Lavigne
There was nothing complicated about Avril's reign in the early aughts. After all, her appearance at the 2003 VMAs was a little over a year after she released her debut album Let Go—and the rest, of course, is history.
Lindsay Lohan
Confessions of a Teenage Drama Red Carpet Queen: The actress, who attended the ceremony just weeks after the premiere of Freaky Friday, wore a black corset paired with a white button-down shirt and denim for her red carpet look.
Beyoncé
Twenty years later and we're still crazy in love with the "Naughty Girl" singer's sparkling look on the red carpet.
Solange Knowles
But Beyoncé wasn't the only Knowles member in the building, as her younger sister Solange was also in attendance.
Jessica Alba
The Honey star, who wore a black leather dress for the event, flashed a sweet smile ahead of the ceremony.
Kim Cattrall
The Sex and the City star was front and center on the red carpet, wearing a stunning sleeveless tan gown with embellished detail.
50 Cent & Vivica A. Fox
The former couple, who began dating earlier that year—they ultimately split in 2004—showed up and showed out in matching grey ensembles.
Black Eyed Peas
The band, which featured Fergie as a member at the time, met MTV more than halfway that year, hitting the stage to perform "Where Is The Love?"
Paris Hilton & Nicky Hilton
Loves it! Paris and Nicky Hilton attended the event as a stylish sister duo.
Christina Aguilera
The "Come on Over Baby" singer had four nominations underneath her belt going in that night, but her onstage kiss with Madonna (alongside Britney, of course) that became the talked-about moment from the ceremony.
Serena Williams & Venus Williams
Game, set, match: The tennis legends were seen posing in matching mini skirts on the red carpet.
Ashanti
The "Rock Wit U" singer, who earned a nomination for Best R&B Video for her single that year, arrived pretty in pink.
Good Charlotte
Flying high from the success of their 2002 song, "Lifestyles of the Rich & Famous," the band earned a nomination that night for Best Rock Video.