The Most Outrageous VMA Beauty Looks of All Time

The Greatest VMA Beauty Moments of All Time: From Kurt Cobain’s Blonde to Britney’s Abs Inline

Amid a sea of glamorous red carpets that revolve around a pitch-perfect blowout or well-executed cat-eye, the MTV Video Music Awards have come to stand out as a beacon of quirk and nonconformity, offering celebrities an occasion to let their hair down—or tie it up, as the case may be—in an off-the-cuff celebration of music and pop culture.

Who could forget Madonna’s revolutionary 1984 performance of “Like a Virgin” at the network’s inaugural event, inspiring a generation of extreme bedhead, brushed-up brows, gleaming décolletage, and playful irreverence? Since then, looks have ranged from coordinated grunge—Kurt Cobain and Courtney Love attended the 1993 ceremony with daughter Frances Bean in tow, each embracing their own shade of shoulder-grazing platinum—to romantic.

The mid-’90s found alternative songstress Fiona Apple embracing Botticelli-worthy waves tied back in a half-up style that amplified her ironically angelic features—ones that she employed later to not-so-sweetly call out the absurdity of pop idolatry while accepting her silver Moonman statuette. Meanwhile, Alanis Morissette’s middle part, hip-grazing weighted lengths, and lightly lined eyes were the very picture of the decade’s rocker insouciance.

Not long afterward, the unofficial exposed midriff dress code was born, spurring everyone from the members of TLC, Jennifer Lopez, and the Spice Girls to Shakira, Miley Cyrus, and Gwen Stefani to flaunt their famously sculpted abs. It was a scene-stealing tactic repeated in 1999, when the red carpet saw a lot of Lil’ Kim, who supplemented her lack of clothing—aka the pasty seen round the world—with an impressive wig of shiny lilac and an era-appropriate plum lip. And in 2001, Britney Spears found the necessary counterpart to her bare, glossy legs and abs in a handful of glitter tattoos and one albino python.

In fact, the VMA red carpet and onstage rebellions have been so iconoclastic that attendees continue to pay homage to the trailblazers that came before, with Cyrus seemingly re-creating Stefani’s trademark look, and Katy Perry honoring Spears and Justin Timberlake’s infamous all-denim couples moment—made newly modern by a cat-eye and full-face bangs.

And it doesn't end there. Beyoncé used the iconic platform to announce her first pregnancy, unbuttoning her sparkly jacket and embracing her bump while her side-swept mane blew majestically behind her. Fast forward to 2016, and the pop star made waves again when she arrived hand-in-hand with daughter Blue Ivy, who wore a glittering frock and sophisticated braids topped with tiara fit for a princess. And last year? Jennifer Lopez owned the night with Rapuzelian blonde, parted down the middle and swinging past her waist, while Nikki Minaj blinked past a supremely graphic cat-eye, black liner pulled into exaggerated swoops that pointed past her browline and toward a seemingly animated updo.

Considering this year's ceremony comes just days after the release of September cover star Taylor Swift's most recent album, Lover, the pop star and her penchant for red lips and saccharine notes are bound to set the stage for an evening of noteworthy beauty. Here, in honor of the pop star-fueled spectacle's unparalleled ability to shock and delight, a look back at the best VMA beauty moments of all time.

Originally Appeared on Vogue