LL Cool J (1985)
With due respect to early bucket hat proponents Big Bank Hank and Devastating Tito, it was Def Jam's teenage rapper who made the fuzzy, fire-red Kangol a hip-hop style essential, earning him the sobriquet of rap's "most recognizable bucket hat stan." (LL also favored the traditional canvas bucket hat, as snapped by legendary photographer Janette Beckman.) Intriguingly, other early bucket hat purveyors include Cool J's putative boss, a young, dusted-out Russell Simmons (the pre-yoga proto-executive paired the bucket hat with tight-fitting polo shirts for a distinctly beach bummy look). The bucket became so inseparable from LL that rumors spread that something was wrong with his head. His arch-rival Kool Moe Dee even used it as a signifier for LL on this How Ya Like Me Now album cover, positioning a red Kangol bucket under the tire of his Jeep.