Who: Jared Leto

When: December 12, 1994

Where: Westwood, California

Why: In his break-out role as Jordan Catalano on the 90s cult hit My So Called Life (canceled after one season but re-aired by MTV after fans petitioned for more), Jared Leto defined the intoxicating, misunderstood, appeal of a bad boy for a new generation. Catalano spent his days leaning hard against the lockers, procuring fake IDs, working on his car, and making-out in the school's boiler room. His nights were spent, of course, at band practice. Ask any woman over 29 what she liked about the show, and she'll immediately flush with erotic nostalgia—Jordan Catalano is definitely at the top of her list. But Leto didn't invent this trope of masculinity. What we can credit him for, is the clear-as-the-ocean blue eyes, chin length dirty hair, and grunge wardrobe. In this photo from the premiere of the film Speechless, Leto is at peak heartthrob. His buffalo plaid jacket suggests some cozy bungalow with a roaring fire, and then there's the hair, which frames his almost too pretty face in DGAF-ness. It perfectly captures the un-pretentious cool of the decade, in line behind only River Phoenix, Johnny Depp, and Kurt Cobain.

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