As far as red carpet looks go, the Grammy Awards are easily the most entertaining, especially compared with the aesthetics of the more restrained—albeit inarguably beautiful—Oscars. Since its inception in 1959, the Grammys have emboldened musicians to experiment and make statements, resulting in a catalog of unique looks representative of both era and genre. It’s the night every year we see celebrities unabashedly lean into trends: Timeless and classic this is not. Instead, it’s often a welcome breath of fun-and-risky fresh air.
Aretha Franklin embodied the ’70s glamorous bohemian aesthetic when she accepted a gilded gramophone with lids dusted in hazy silver—her dense, close-cropped Afro wrapped in a scarf. Skip ahead a decade and Joan Jett’s trademark raven shag paired with graphic pink blush and eyes rimmed in smudged onyx served as a visual portal to the ’80s. Alanis Morissette and Fiona Apple rounded out the ’90s I-don’t-care-if-you-like-it songwriter vibe with tangled and messy hair—and Britney Spears and Jennifer Lopez showed us the exact opposite in the early aughts pop-era, marked by highlighted, ironed styles, sweet smiles, and plunging necklines. From Madonna‘s geometric black bob to Beyoncé’s golden headpiece and natural hip-grazing spirals, scroll through the gallery above for 20 memorable moments that demonstrate the undeniable power of live-for-the-moment beauty.