Who started it: LL Cool J
Circa: Late '80s 

Sugar Hill Gang's Big Bank Hank has the honor of being the first rapper to wear a bucket hat in a rap video (the first rap music video, to be exact), and Run D.M.C. switched up to Kangol bucket hats from time to time—although Jam Master Jay apparently thought they were wack—but no rapper adopted the fuzzy Kangol and made it as mainstream as LL Cool J. Every now and then he switched it up with a canvas version, but his endorsement of the  bucket hat took the Kangol logo from dope accessory to must-have piece.